(c) One sigma and two pi bonds

(d) Two sigma and two pi bonds

12. Which of the following types of isomerism is shown by pentanone
(a) Chain isomerism (b) Position isomerism
(c) Functional isomerism (d) All of these
13. IUPAC name of CCl 3 CHO is [MP PMT/PET 1988]
Introduction (a) Chloral (b) Trichloro acetaldehyde
(c) 1, 1, 1-trichloroethanal (d) 2, 2, 2-trichloroethanal
1. Reaction of acetaldehyde with HCN followed by hydrolysis gives a 14. Which of the following is a mixed ketone [AFMC 1997]
compound which shows [MP PET 1997] (a) Pentanone (b) Acetophenone
(a) Optical isomerism (b) Geometrical isomerism
(c) Benzophenone (d) Butanone
(c) Metamerism (d) Tautomerism
15. Chloral is [CPMT 1976, 84]
2. In aldehydes and ketones, carbon of carbonyl group is
[MP PMT 1995; RPET 1999, 2000] (a) CCl 3 CHO (b) CCl 3 COCH 3
(a) sp 3 hybridised (b) sp 2 hybridised (c) CCl 3 COCCl 3 (d) CCl 3 CH 2 OH
(c) sp hybridised (d) Unhybridised 16. Carbonyl compounds are usually
3. The IUPAC name of the following structure is (a) Ethers, aldehydes, ketones and carboxylic acids
CH 3 O (b) Aldehydes, ketones and carboxylic acids
| ||
CH 3  CH  C  CH 2  CH 2 OH [MP PMT 1995] (c) Aldehydes and ketones
(a) 1-hydroxy 4-methyl 3-pentanone (d) Carboxylic acids
(b) 2-methyl 5-hydroxy 3-pentanone 17. Acetone and acetaldehyde are [KCET 1998]
(c) 4-methyl 3-oxo 1-pentanol (a) Position isomers (b) Functional isomers
(d) Hexanol-1, one-3 (c) Not isomers (d) Chain isomers
4. Glyoxal is [BVP 2003] 18. Which of the aldehyde is most reactive ? [DCE 2004]
(a) CH 2O  CH 2O (b) CH 2 OH (a) C6 H 5  CHO (b) CH 3 CHO
|
CH 2OH (c) HCHO (d) All the equally reactive
(c) CHO (d) CH 2 OH
| | Preparation
CHO CHO
5. Aldehydes are isomeric with 1. The end product in the following sequence of reaction is
(a) Ketones (b) Ethers
HC  CH    A 
1%HgSO 4
 B 
CH 3 MgX

[O ]
(c) Alcohols (d) Fatty acids 20 % H 2 SO 4
6. Which of the following compounds does not contain an OH [Bihar CEE 2002]
group [CPMT 1982] (a) Acetic acid (b) Isopropyl alcohol
(a) Phenol (b) Carboxylic acid (c) Acetone (d) Ethanol
(c) Aldehydes (d) Alcohols
O
7. IUPAC name of CH 3 COCH 3 is [MP PET 1991] ||
(a) Acetone (b) 2-propanone 2. In the following reaction, product P is R  C  Cl 
 P [CBSE PMT 19
H2
Pd  BaSO 4
(c) Dimethyl ketone (d) Propanal
IIT 1992; AIIMS 1997; AFMC 1998]
8. What is the compound called if remaining two valencies of a
carbonyl group are satisfied by two alkyl groups (a) RCH 2 OH (b) R COOH
[CPMT 1990]
(c) RCHO (d) RCH 3
(a) Aldehyde (b) Ketone
(c) Acid (d) Acid chloride 3. Acetophenone is prepared from [CPMT 2003]
OH (a) Rosenmund reaction
|
(b) Sandmayer reaction
9. CH 3  C  CN is
| (c) Wurtz reaction
H (d) Friedel craft reaction
(a) Acetaldehyde cyanohydrin 4. Compound which gives acetone on ozonolysis
(b) Acetone cyanohydrin [UPSEAT 2003]
(c) Cyanoethanol
(d) Ethanol nitrile (a) CH 3  CH  CH  CH 3 (b) (CH 3 )2 C  C(CH 3 )2
10. Ethanedial has which functional group(s) (c) C6 H 5 CH  CH 2 (d) CH 3 CH  CH 2
(a) One ketonic (b) Two aldehydic
NaOH
(c) One double bond (d) Two double bond 5. CH 3  C  CH 2  COOC 2 H 5   A,
||
H 2O
R O
11. In the group C  O the carbonyl carbon is joined to other
R product ‘A’ in the reaction is [RPMT 2003]
atoms by (a) CH 3 COOH (b) C 2 H 5 OH
(a) Two sigma and one pi bonds
(b) Three sigma and one pi bonds (c) CH 3 COCH 3 (d) C 2 H 5 CHO
6. Which one of the following compounds is prepared in the (a) Phenol and acetic acid
laboratory from benzene by a substitution reaction (b) Benzene and acetone
[EAMCET 2003] (c) Benzene and acetyl chloride
(a) Glyoxal (b) Cyclohexane (d) Phenol and acetone
(c) Acetophenone (d) Hexabromo cyclohexane 17. Isopropyl alcohol on oxidation gives
7. Ketones (R  C  R1 ) where R  R1  alkyl group. It can be [RPMT 1997; BHU 1997]
||
O (a) Acetone (b) Acetaldehyde
obtained in one step by [CBSE PMT 1997] (c) Ether (d) Ethylene
(a) Hydrolysis of esters 18. On heating calcium acetate and calcium formate, the product
(b) Oxidation of primary alcohol formed is
(c) Oxidation of secondary alcohol [DPMT 1984; EAMCET 1985; MP PMT 1996, 92;
KCET 1990; CPMT 1979, 82, 84; BIT 1992; RPET 2000]
(d) Reaction of acid halide with alcohols
8. Predict the product ‘B’ in the sequence of reaction (a) CH 3 COCH 3 (b) CH 3 CHO
HC  CH   A 
30 % H 2 SO 4
 B
NaOH
[CBSE PMT 2001] (c) HCHO  CaCO 3 (d) CH 3 CHO  CaCO3
HgSO 4
19. Which of the following compound gives a ketone with Grignard
(a) CH 3 COONa (b) CH 3 COOH reagent [CPMT 1988; MP PET 1997]
(c) CH 3 CHO (d) CH 3  CH  CH 2 CHO (a) Formaldehyde (b) Ethyl alcohol
| (c) Methyl cyanide (d) Methyl iodide
OH
20. In the Rosenmund's reduction, BaSO4 taken with catalyst Pd acts
9. CH 3 COCl  CH 3 CHO  HCl;
2H
as
Pd / BaSO 4
(a) Promotor (b) Catalytic poison
The above reaction is called [JIPMER 1997] (c) Cooperator (d) Absorber
(a) Reimer-Tiemann reaction (b) Cannizzaro reaction 21. The Clemmenson reduction of acetone yields
(c) Rosenmund reaction (d) Reformatsky reaction (a) Ethanol (b) Ethanal
10. The oxidation of toluene to benzaldehyde by chromyl chloride is (c) Propane (d) Propanol
called
[CBSE PMT 1996; AFMC 1998, 99; AIIMS 2000; 22. Catalyst SnCl 2 / HCl is used in [BHU 1995]
JIPMER 2001; AFMC 2001; DCE 2004] (a) Stephen's reduction
(a) Cannizzaro reaction (b) Wurtz reaction (b) Cannizzaro reaction
(c) Etard reaction (d) Reimer-Tiemann reaction (c) Clemmensen's reduction
11. From which of the following tertiary butyl alcohol is obtained by the (d) Rosenmund's reduction
action of methyl magnesium iodide 23. Methyl ethyl ketone is prepared by the oxidation of
[MP CET 2000] [IIT-JEE 1987; MP PMT 1992]
(a) HCHO (b) CH 3 CHO (a) 2-propanol (b) 1-butanol
(c) CH 3 COCH 3 (d) CO 2 (c) 2-butanol (d) t-butyl alcohol
24. Benzaldehyde can be prepared by oxidation of toluene by
12. Catalyst used in Rosenmund reduction is [Bihar MEE 1997]
[BHU 1986]
(a) Pd / BaSO 4 (b) Zn-Hg couple (a) Acidic KMnO4 (b) K2Cr2O7
(c) LiAlH4 (d) Ni / H 2 (c) CrO2 Cl 2 (d) All of these
13. CH 3  CH 2  C  CH  Butanone, R is
R
[BHU 2003] 25. C6 H 6  CO  HCl  X  HCl
Anhy AlCl3
H 2O
Compound X is [DPMT 1979, 83]
(a) Hg   (b) KMnO4
(a) C6 H 5 CH 3 (b) C6 H 5 CH 2Cl
(c) KClO3 (d) K2Cr2O7
(c) C6 H 5 CHO (d) C6 H 5 COOH
14. Dry heating of calcium acetate gives
26. Which of the following gases when passed through warm dilute
[DPMT 1979, 81, 96; NCERT 1981; KCET 1993;
Bihar CEE 1995; MNR 1986; MP PMT 1997; solution of H 2 SO 4 in presence of HgSO 4 gives acetaldehyde
MP PET 1993, 95; JIPMER 2002; AIIMS 1996; (a) CH 4 (b) C2 H 6
CPMT 1982, 86, 96, 2003; RPMT 2002]
(c) C2 H 4 (d) C2 H 2
(a) Acetaldehyde (b) Ethane
(c) Acetic acid (d) Acetone 27. CH 3 COCH 3 can be obtained by [CBSE PMT 1992]
15. Identify the product C in the series (a) Heating acetaldehyde with methanol
CH 3 CN    A 
Na / C2 H 5 OH
 B 
HNO 2
 C
Tollen's reagent (b) Oxidation of propyl alcohol
[MP PET 1999]
(c) Oxidation of isopropyl alcohol
(d) Reduction of propionic acid
(a) CH 3 COOH (b) CH 3 CH 2 NHOH
28. Propyne on hydrolysis in presence of HCl and HgSO4 gives[DPMT 1980; CPMT
(c) CH 3 CONH 2 (d) CH 3 CHO (a) Acetaldehyde (b) Acetone
16. Acetophenone is prepared by the reaction of which of the following (c) Formaldehyde (d) None of these
in the presence of AlCl3 catalyst [AIIMS 1996]
29. Which of the following on reaction with NH 3 gives urinary (a) Pb / BaSO4 (b) alkaline KMnO4
antiseptic compound [MP PMT 1999] (c) acidic KMnO4 (d) CO  HCl
(a) HCHO (b) CH 3 CHO
CH 3

(c) C 6 H 5 CHO (d) C 6 H 5 CH 2 CHO 42. On reductive ozonolysis yields

[Orissa JEE 2005]
30. The oxidation product of 2-propanol with hot conc. HNO 3 is [JIPMER 1997]
(a) 6-oxoheptanal (b) 6-oxoheptanoic acid
(a) Ethanoic acid (b) Propanone (c) 6-hydroxyheptanal (d) 3-hydroxypentanal
(c) Propanal (d) None of these 43. An alkene of molecular formula C9 H18 on ozonolysis gives 2,2
31. Hydrolysis of ozonide of 1-butene gives [Kerala PMT 2003]
dimethyl propanal & 2-butanon, then the alkene is
(a) Ethylene only [Kerala CET 2005]
(b) Acetaldehyde and Formaldehyde (a) 2, 2, 4-trimethyl –3-hexene
(c) Propionaldehyde and Formaldehyde (b) 2, 2, 6-trimethyl-3-hexene
(d) Acetaldehyde only (c) 2, 3, 4-trimethyl-2-hexene
(e) Acetaldehyde and Oxalic acid (d) 2, 2, 4-trimethyl-2-hexene
32. Ketones are prepared by (e) 2, 2dimethyl-2-heptene
(a) Clemmensen's reduction (b) Cannizzaro reaction
(c) Rosenmund's reduction (d) Oppenaur's oxidation
Properties
33. O3 reacts with CH 2  CH 2 to form ozonide. On hydrolysis it
forms [MP PET 1986, 90] 1. Identify the reactant X and the product Y
(a) Ethylene oxide (b) HCHO
CH 3  CO  CH 3  X  (CH 3 )3 C  OMg  Cl
(c) Ethylene glycol (d) Ethyl alcohol
34. Ethyne on reaction with water in the presence of HgSO4 and Hydrolysis
H 2 SO 4 gives [UPSEAT 1999; BVP 2003] Y  Mg (OH ) Cl
(a) Acetone (b) Acetaldehyde [Kerala PMT 2003]
(c) Acetic acid (d) Ethyl alcohol (a) X  MgCl2 ; Y  CH 3 CH  CH 2
35. CH 3  CH 2  C  CH   A, the compound A is
HgSO 4
(b) X  CH 3 MgCl; Y  C 2 H 5 COCH 3
H 2 SO 4
[Orissa JEE 2004] (c) X  CH 3 MgCl; Y  (CH 3 )3 C  OH
O (d) X  C 2 H 5 MgCl; Y  (CH 3 )3 C  OH
||
(a) CH 3  CH 2  C  CH 3 2. When m-chlorobenzaldehyde is treated with 50% KOH solution, the
product (s) obtained is (are)
(b) CH 3  CH 2  CH 2  CHO
[CBSE PMT 2003]
(c) CH 3  CH 2  CH 2  COOH OH OH
(d) None of these (a) CH – CH
36. When a mixture of methane and oxygen is passed through heated
molybdenum oxide, the main product formed is
[KCET 2004]
(a) Methanoic acid (b) Ethanal OH OH
(c) Methanol (d) Methanal
37. Benzoin is [KCET 2004] (b) COO  CH 2 OH
(a) Compound containing an aldehyde and a ketonic group
+
(b) , -unsaturated acid
(c) -hydroxy aldehyde
(d) -hydroxy ketone OH OH
38. The oxidation of benzyl chloride with lead nitrate gives (c)
[MP PMT 2004] COO  CH 2 OH
(a) Benzyl alcohol (b) Benzoic acid
(c) Benzaldehyde (d) p-chlorobenzaldehyde +
39. R  CH  CH 2  CO  H 2
Cl Cl
  RCH 2CH 2CHO.
High Temp
[DPMT 2004] (d)
High Pressure
OH OH
The above reaction is
(a) Mendius reaction (b) Oxo process CH – CH
(c) Sandorn's reaction (d) Stephen's reaction
40. Glycerol reacts with potassium bisulphate to produce
3. A and B in the following reactions are
[Pb. CET 2003]
(a) Allyl iodide (b) Allyl sulphate Cl R Cl OH
R  C  R  HCN
 A  B
C
(c) Acryl aldehyde (d) Glycerol trisulphate || KCN R CH 2 NH 2
41. The reagent used in Gatterman Koch aldehyde synthesis is O
[CPMT 2004] [CBSE PMT 2003]
 CN 12. Which of the following products is formed when benzaldehyde is
(a) A  RR' C , B  LiAlH4 treated with CH 3 MgBr and the addition product so obtained is
OH
subjected to acid hydrolysis
OH
(b) A  RR' C , B  NH 3 [Haryana CEET 2000]
COOH (a) Secondary alcohol (b) A primary alcohol
CN (c) Phenol (d) Tert-Butyl alcohol
(c) A  RR' C , B  H3O 13. Aldol condensation will not be observed in [GATE 2001]
OH
(a) Chloral (b) Phenyl acetaldehyde
(d) A  RR' CH 2 CN , B  NaOH
(c) Hexanal (d) Ethanol
4. Reduction of Aldehydes and Ketones to hydrocarbon take place in 14. Which of the following compounds containing carbonyl group will
the presence of [CPMT 2003]
give coloured crystalline compound with
(a) Zn amalgam and HCl acid
(b) Pd / BaSO4 NHNH 2
(c) Anhydrous AlCl3
(d) Ni/Pt O2 N NO 2 [Kerala (Med.) 2001]
5. Reduction of  C  O to CH 2 can be carried out with (a) CH 3 COCl (b) CH 3 COCH 3
[DCE 2000]
(a) Catalytic reduction (b) Na / C2 H 5 OH (c) CH 3 CO(OC2 H 5 ) (d) CH 3 CONH 2

(c) Wolf-Kischner reduction (d) LiAlH4 (e) HO(C6 H 4 )COOH

6. For C6 H 5 CHO which of the following is incorrect 15. Which of the following organic compounds exhibits positive Fehling
[CPMT 1985] test as well as iodoform test
(a) On oxidation it yields benzoic acid [MP PET 1994; KCET 2001]
(b) It is used in perfumery (a) Methanal (b) Ethanol
(c) It is an aromatic aldehyde (c) Propanone (d) Ethanal
(d) On reduction yields phenol 16. Which of the following compound will undergo self aldol
7. Grignard reagent on reaction with acetone forms condensation in the presence of cold dilute alkali
[BHU 1995; RPMT 2002; Roorkee 1990] [CBSE PMT 1994]
(a) Tertiary alcohol (b) Secondary alcohol (a) C 6 H 5 CHO (b) CH 3 CH 2CHO
(c) Acetic acid (d) Acetaldehyde
8. Which of the following is incorrect [CBSE PMT 2001] (c) CH  C  CHO (d) CH 2  CH  CHO
(a) FeCl3 is used in the detection of phenols 17. Acetaldehyde when treated with dilute NaOH gives
(b) Fehling solution is used in the detection of glucose [EAMCET 1998]
(c) Tollen’s reagent is used in detection of unsaturation (a) CH 3 CH 2 OH
(d) NaHSO 3 is used in the detection of carbonyl compounds (b) CH 3 COOH
9. Consider the following statement Acetophenone can be prepared by
(c) CH 3  CH  CH 2  CHO
(1) Oxidation of 1-phenylethanol |
(2) Reaction of benzalthanol with methyl magnesium bromide OH
(3) Friedel craft’s reaction of benzene with acetyl chloride (d) CH 3  CH 3
(4) Distillation of calcium benzoate [SCRA 2001]
18. C 2 H 5 CHO and (CH 3 )2 CO can be distinguished by testing
(a) 1 and 2 (b) 1 and 4
(c) 1 and 3 (d) 3 and 4 with [EAMCET 1998; CPMT 1994, 97; MP PET 1995;
10. Which one of the following pairs is not correctly matched MP PMT 1996; RPMT 1997, 99]
[SCRA 2001] (a) Phenyl hydrazine (b) Hydroxylamine
(c) Fehling solution (d) Sodium bisulphite
(a)  C  O   CH 2
Clemenson' s reduction
19. Which of the following will undergo aldol condensation
(b)  C  O    CHOH
Wolf- Kishner reduction
[IIT 1998]
(c)  COCl  CHO
Rosenmund' s reduction (a) Acetaldehyde (b) Propanaldehyde
(c) Benzaldehyde (d) Trideuteroacetaldehyde
(d)  C  N    CHO
Stephen reduction
20. Which of the following oxidation reactions can be carried out with
11. Which of the following gives aldol condensation reaction
[CPMT 2001] chromic acid in aqueous acetone at 5  10 o C
[Roorkee Qualifying 1998]
O
|| (a) CH 3 (CH 2 )3 C  C  CH  CH 3 
(a) C6 H 5 OH (b) C6 H 5  C  C6 H 5 |
O
OH ||
O O CH 3 (CH 2 )3 C C C CH 3
|| ||
(c) CH 3 CH 2  C  CH 3 (d) (CH 3 )3 C  C  CH 3 (b) CH 3 (CH 2 )3 CH  CH  CH 2 OH 
CH 3 (CH 2 )3 CH  CH  CHO
 (c) C 6 H 5 CH 3  C 6 H 5 COOH [Pb. CET 1985]
(a) An aldehyde (b) A ketone
(d) CH 3 (CH 2 )3 CH 2 OH  CH 3 (CH 2 )3 CHO (c) A primary alcohol (d) A secondary alcohol
21. Acetaldehyde cannot show [AIIMS 1997] 35. Treatment of propionaldehyde with dilute NaOH solution gives
(a) Iodoform test (b) Lucas test (a) CH 3 CH 2 COOCH 2 CH 2 CH 3
(c) Benedict's test (d) Tollen's test (b) CH 3 CH 2CHOHCH (CH 3 )CHO
22. Benzaldehyde NaOH  (c) CH 3 CH 2CHOHCH 2CH 2CHO
[CPMT 1997, 2001; CBSE PMT 1999; Pb. PMT 1999]
(d) CH 3 CH 2COCH 2CH 2CHO
(a) Benzyl alcohol (b) Benzoic alcohol
36. Aldol condensation of acetaldehyde involves the formation of which
(c) Hydrobenzamide (d) Cinnamic acid of the following intermediate [Pb. CET 1986]
23. The following reagent converts C 6 H 5 COCHO to (a) Acetate ion (b) A carbanion
C 6 H 5 CHOHCOONa [Roorkee Qualifying 1998] (c) A carbonium ion (d) A free radical
37. 3CH 3 COCH 3  (CH 3 )2 C  CH  CO  CH  C(CH 3 )2
HCl
(a) Aq. NaOH (b) Acidic Na 2 S 2 O 3
This polymer (B) is obtained when acetone is saturated with
(c) Na 2 CrO4 / H 2 SO 4 (d) NaNO 2 / HCl hydrogen chloride gas, B can be [CBSE PMT 1989]
(a) Phorone (b) Formose
24. Benzyl alcohol and sodium benzoate is obtained by the action of
sodium hydroxide on benzaldehyde. This reaction is known as (c) Diacetone alcohol
[KCET 2005] (d) Mesityl oxide
(a) Perkin’s reaction (b) Cannizzaro’s reaction 38. Aromatic aldehydes undergo disproportionation in presence of
sodium or potassium hydroxide to give corresponding alcohol and
(c) Sandmeyer’s reaction (d) Claisen condensation acid. The reaction is known as [MNR 1987]
25. To distinguish between formaldehyde and acetaldehyde, we require [Orissareaction
(a) Wurtz's PMT 1987] (b) Cannizzaro reaction
(a) Tollen's reagent (b) Fehling's solution (c) Friedel-Craft's reaction (d) Claisen reaction
(c) Schiff's reagent (d) Caustic soda solution 39. m-chlorobenzaldehyde on reaction with conc. KOH at room
26. Which of the following does not give iodoform test temperature gives [IIT-JEE 1991]
[AIIMS 1992; MP PMT 1990, 96; CET Pune 1998 (a) Potassium m-chlorobenzoate and m-hydroxy benzaldehyde
DPMT 1981; CPMT 1976] (b) m-hydroxy benzaldehyde and m-chlorobenzyl alcohol
(a) CH 3 CH 2OH (b) CH 3 OH (c) m-chlorobenzyl alcohol and m-hydroxy benzyl alcohol
(d) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol
(c) CH 3 CHO (d) PhCOCH 3
40. Which of the following does not give yellow precipitate with
27. Which of the following will not give iodoform test NaOH  KI [MP PMT 1997]
[Kurukshetra CEE 1991; Bihar CEE 1995; (a) Acetone (b) Acetaldehyde
CBSE PMT 1998; MP PMT 2004] (c) Benzaldehyde (d) Acetophenone
(a) Ethanal (b) Ethanol
41. The alkaline CuSO 4 containing sodium potassium tartrate does
(c) 2-propanone (d) 3-pentanone
not react with [MP PMT 1997]
28. Which of the following will not give the iodoform test
[MNR 1994] (a) CH 3 CHO (b) C 2 H 5 CHO
(a) Acetophenone (b) Ethanal (c) C 6 H 5 CH 2 CHO (d) C 6 H 5 CHO
(c) Benzophenone (d) Ethanol
42. Correct order of reactivity of CH 3 CHO, C 2 H 5 COCH 3 and
29. Haloform test is given by the following substance
[EAMCET 1988] CH 3 COCH 3 is [MP PMT 1991]
(a) HCHO (b) (CH 3 )2 CO (a) CH 3CHO  CH 3COCH 3  CH 3COC 2 H5
(c) CH 3 OCH 3 (d) CH 3 CH 2Cl (b) C2 H5 COCH 3  CH 3 COCH 3  CH 3 CHO
30. Dimethyl ketones are usually characterised through (c) CH 3COCH 3  CH 3CHO  C2 H5 COCH 3
[MNR 1992]
(a) Tollen's reagent (b) Iodoform test (d) CH 3COCH 3  C2 H5 COCH 3  CH 3 CHO
(c) Schiff's test (d) Benedict's reagent 43. One mole of an organic compound requires 0.5 mole of oxygen to
31. The light yellow compound produced when acetone reacts with produce an acid. The compound may be
iodine and alkali, is [MP PMT 1992; EAMCET 1993] [NCERT 1981]
(a) CH 3 .[Link] 2 I (b) CH 3 I (a) Alcohol (b) Ether
(c) Ketone (d) Aldehyde
(c) CHI 3 (d) None of these 44. Aldehydes can be oxidised by [NCERT 1983]
32. If formaldehyde and KOH are heated, then we get (a) Tollen's reagent (b) Fehling solution
[MP PET 1999; KCET 2000] (c) Benedict solution (d) All of these
(a) Acetylene (b) Methane 45. Silver mirror is a test for [DPMT 1983; CBSE PMT 1988]
(c) Methyl alcohol (d) Ethyl formate
(a) Aldehydes (b) Thio alcohols
33. Which of the following reagent reacts differently with
(c) Amines (d) Ethers
HCHO, CH 3 CHO and CH 3 COCH 3 [MP PET 1999]
46. CH 3 CH  CHCHO is oxidised to CH 3 CH  CHCOOH
(a) HCN (b) NH 2 NH 2 using [NCERT 1978]
(c) NH 2 OH (d) NH 3 (a) Alkaline KMnO4 (b) Selenium dioxide
34. Acetaldehyde reacts with C2 H 5 MgCl the final product is (c) Ammoniacal AgNO3 (d) All of these
47. Which of the following does not turn Schiff's reagent to pink 61. Glucose molecule reacts with X number of molecules of
[DPMT 1981; CPMT 1989] phenylhydrazine to yield osazone. The value of X is
[CBSE PMT 1998]
(a) Formaldehyde (b) Benzaldehyde
(a) One (b) Two
(c) Acetone (d) Acetaldehyde (c) Three (d) Four
48. Fehling's test is positive for [KCET 1993] 62. In which of the following reactions aromatic aldehyde is treated with
(a) Acetaldehyde (b) Benzaldehyde acid anhydride in presence of corresponding salt of the acid to give
(c) Ether (d) Alcohol unsaturated aromatic acid
49. Acetaldehyde and acetone differ in their reaction with [BHU 1998, KCET (Med.) 2001]
[KCET 1989] (a) Friedel-Craft's reaction (b) Perkin reaction
(a) Sodium bisulphite (c) Wurtz reaction (d) None of these
(b) Ammonia 63. 2CH 3  C  CH 3 Mg
/Hg
 Product, product in the reaction is[RPMT 2003]
(c) Phosphorus pentachloride || H
(d) Phenyl hydrazine O
50. The final product formed when acetaldehyde is reduced with sodium CH 3 CH 3
and alcohol is [BHU 1976] | |

(a) Ethylene (b) Ethyl alcohol (a) H 3 C  C  C  CH 3 (b) CH 3  C  O  C  CH 3

| | || ||
(c) Ethene (d) All of these OH OH O O
51. The compound obtained by the reduction of propionaldehyde by
amalgamated zinc and concentrated HCl is (c) CH  CH1983]
[MP3 PMT  CH  CH 3 (d) None of these
| |
(a) Propanol (b) Propane OH OH
(c) Propene (d) All of these 64. Cinnamic acid is formed when C6 H 5  CHO condenses with
52. Formaldehyde when treated with KOH gives methanol and
potassium formate. The reaction is known as (CH 3 CO )2 O in presence of [Orissa JEE 2003]
[MP PET 1997] (a) Conc. H 2 SO 4 (b) Sodium acetate
(a) Perkin reaction (b) Claisen reaction
(c) Cannizzaro reaction (d) Knoevenagel reaction (c) Sodium metal (d) Anhydrous ZnCl2
53. Aldehydes and ketones give addition reaction with 65. A mixture of benzaldehyde and formaldehyde on heating with
[KCET 1992] aqueous NaOH solution gives
(a) Hydrazine (b) Phenyl hydrazine [IIT-JEE (Screening) 2001]
(c) Semicarbazide (d) Hydrogen cyanide (a) Benzyl alcohol and sodium formate
(e) All of these (b) Sodium benzoate and methyl alcohol
54. Acetaldehyde reacts with [CBSE PMT 1991] (c) Sodium benzoate and sodium formate
(a) Electrophiles only (d) Benzyl alcohol and methyl alcohol
(b) Nucleophiles only 66. The reaction,
(c) Free radicals only O
(d) Both electrophiles and nucleophiles ||
H  or OH 
CH 3  C  OCH 3  C 2 H 5 OH 
55. The typical reactions of aldehyde is [Pb. CET 1986]
(a) Electrophilic addition (b) Nucleophilic substitution O
||
(c) Nucleophilic addition (d) Nucleophilic elimination CH 3  C  OC2 H 5  CH 3 OH is called [MP PMT 2003]
56. Which will not give acetamide on reaction with ammonia
[CPMT 1985] (a) Perkin’s reaction (b) Claisen Schmidt reaction
(a) Acetic acid (b) Acetyl chloride (c) Esterification (d) Trans-esterification
(c) Acetic anhydride (d) Methyl formate 67. Formaldehyde reacts with ammonia to give urotropine. The formula
of urotropine is
57. The addition of HCN to carbonyl compounds is an example of [Haryana CEET 2000] [MP PMT 1989, 96, 2003; AIIMS 1982; NCERT 1987;
(a) Nucleophilic substitution MP PET 1990, 91, 2000; CPMT 1978, 82, 86, 97; KCET 2003]
(b) Electrophilic addition (a) (CH 2 )6 N 4 (b) (CH 2 )4 N 3
(c) Nucleophilic addition
(c) (CH 2 )6 N 6 (d) (CH 2 )3 N 3
(d) Electrophilic substitution
58. Which of the following reagents is used to distinguish acetone and 68. Aldol condensation will not take place in
acetophenone [RPMT 2002; KCET 1998] [CBSE PMT 1996, 99; RPMT 1999; CPMT 1988, 04]

(a) NaHSO 3 (b) Grignard reagent (a) HCHO (b) CH 3 CH 2 CHO

(c) Na SO (d) NH Cl (c) CH 3 CHO (d) CH 3 COCH 3

2 4 4
69. Contents of three bottles were found to react
59. The product formed by the reaction of chlorine with benzaldehyde
in the absence of a catalyst is (i) Neither with Fehling's solution nor with Tollen's reagent
[Tamil Nadu CET 2002] (ii) Only with Tollen's reagent but not with Fehling's solution
(a) Chlorobenzene (b) Benzyl chloride (iii) With both Tollen's reagent and Fehling's solution.
(c) Benzoyl Chloride (d) o-Chlorobenzaldehyde If they contained either ethanal (acetaldehyde) or propanone
(acetone) or benzal (benzaldehyde), which bottle contained which
60. Which of the following compound is resistant to nucleophilic attack
by hydroxyl ions (a) In (i) benzal, in (ii) ethanal and in (iii) propanone
[CBSE PMT 1998; KCET (Med.) 2001; AFMC 2001] (b) In (i) benzal, in (ii) propanone and in (iii) ethanal
(a) Methyl acetate (b) Acetonitrile (c) In (i) propanone, in (ii) benzal and in (iii) ethanal
(c) Dimethyl ether (d) Acetamide (d) In (i) propanone, in (ii) ethanal and in (iii) benzal
70. Action of hydrazine on aldehydes and ketones gives compound of R
the general structure R |
83. Reaction CO  HCN  R  C  OH is
(a)  C  N  NH 2 R |
CN
(b)  C  N  OH [Kurukshetra CEE 1998; IIT 1990]
(c)  C  N  NH  CONH 2 (a) Electrophilic substitution
(d)  C  N  NH  C 6 H 5 (b) Electrophilic addition
(c) Nucleophilic addition
71. The reaction in which sodium cyanide is used
[MP PET/PMT 1998]
(d) Nucleophilic substitution
(a) Perkin reaction (b) Reimer-Tiemann reaction 84. Benzaldehyde on reaction with acetophenone in the presence of
sodium hydroxide solution gives [BVP 2003]
(c) Benzoin condensation (d) Rosenmund reaction
72. Which one of the following reactions is a method for the conversion (a) C6 H 5 CH  CHCOC 6 H 5
of a ketone into a hydrocarbon (b) C 6 H 5 COCH 2 C 6 H 5
[MP PET/PMT 1998; CBSE PMT 1989]
(a) Aldol condensation (b) Reimer-Tiemann reaction (c) C 6 H 5 CH  CHC 6 H 5
(c) Cannizzaro reaction (d) Wolf-Kishner reduction (d) C6 H 5 CH (OH)COC 6 H 5
73. Bakelite is a polymer of [DPMT 1996; MP PET 2002]
85. Aldehydes and ketones can be reduced to hydrocarbon by using
(a) HCHO  phenol (a) LiAlH4 (b) H 2 / Pd  BaSO 4
(b) HCHO  aldehyde (acetaldehyde)
(c) Na  Hg / HCl (d) NH 2  NH 2 / C 2 H 5 ONa
(c) Phenol  H 2 SO 4
86. An important reaction of acetone is autocondensation in presence of
(d) HCHO  acetone concentrated sulphuric acid to give the aromatic compound
74. Clemmenson reduction involves  C  O to  CH 2 in presence [KCET 2003; MP PET 1986, 89; MP PMT 1992, 2000]
of [DPMT 1996] (a) Mesitylene (b) Mesityl oxide
(a) Zn / Hg (b) Alcohol (c) Trioxan (d) Phorone
(c) Zn dust (d) Zn / alcohol 87. Identify the organic compound which, on heating with strong
75. Aldol condensation involving CH 3 CHO  CH 3 CHO gives the solution of NaOH , partly converted into an acid salt and partly
into alcohol [KCET 2003]
product [DPMT 1996]
(a) Benzyl alcohol (b) Acetaldehyde
(a) CH 3 CHOHCH 2 CHO (b) CH 3 COCH 2 CH 3 (c) Acetone (d) Benzaldehyde
(c) CH 3 CH  CH 2 (d) None of these 88. Which of the following does not give brick red precipitate with
Fehling solution [AIIMS 1996]
76. Enol content is highest in [Orissa JEE 2005]
(a) Acetone (b) Acetaldehyde
(a) Acetone (b) Acetophenone
(c) Formalin (d) D-glucose
(c) Acetic acid (d) Acetyl acetone
89. Acetaldehyde and acetone can be distinguished by
77. Which one of the following reacts with HCN and Tollen's reagent, [AIIMS 1996; DCE 1999; Pb. CET 2000]
but is not oxidised by Fehling's solution
(a) Molisch test (b) Bromoform test
(a) Methanal (b) Ethanal
(c) Solubility in water (d) Tollen's test
(c) Benzaldehyde (d) Acetone
78. During reaction of benzaldehyde with alkali one of the product is 90. Which compound is soluble in H 2 O [RPMT 1997]
(a) Phenol (b) Benzyl alcohol (a) HCHO (b) CH 3 CHO
(c) Benzene (d) Benzophenone (c) CH 3 COCH 3 (d) All
79. Cannizzaro reaction is given by [DPMT 1996]
91. CH 3 CHO  CH 3 MgBr  Product   A
H 2O
(a) HCHO (b) CH 3 COCH 3
What is A ? [RPMT 1997]
(c) CH 3 CHO (d) CH 3 CH 2 OH (a) Primary alcohol (b) Secondary alcohol
(c) Tertiary alcohol (d) Ketone
80. The reaction
92. Which gives lactic acid on hydrolysis after reacting with HCN [UPSEAT 2003; MP
C 6 H 5 CHO  CH 3 CHO  C 6 H 5 CH  CH  CHO
(a) HCHO (b) CH 3 CHO
is known as [BHU 1996]
(a) Perkin's reaction (b) Claisen condensation (c) C 6 H 5 CHO (d) CH 3 COCH 3
(c) Benzoin condensation (d) Cannizzaro's reaction 93. CH 3 CHO react with aqueous NaOH solution to form
81. When two molecules of acetaldehyde condense in the presence of [MP PMT 1992]
dilute alkali, it forms [Bihar MEE 1996] (a) 3-hydroxy butanal (b) 2-hydroxy butanal
(a) Acetal (b) Sodium formate (c) 4-hydroxy butanal (d) 3-hydroxy butanol
(c) Aldol (d) Mesitylene 94. Fehling solution react with HCHO to form precipitate of
(e) None of these [MP PMT 1992]
82. Acetaldehyde on treatment with dil. NaOH followed by heating gives (a) White
[CETcolour
Pune 1998] (b) Yellow colour
(a) CH 3 CH 2 CH 2 CH 2 OH (c) Red colour (d) Blue colour
95. Product in following reaction is
(b) CH 3 CH 2 CH 2 CHO CH 3 MgI  HCHO  Product
(c) CH 3  CH  CHCHO [RPMT 2003; BHU 1998, 2005; DCE 1999]
(d) CH 3  CH  CHCH 2 OH (a) CH 3 CHO (b) CH 3 OH
 (c) C2 H 5 OH (d) CH 3  O  CH 3 (a) Fehling's solution (b) Tollen's reagent

(c) Schiff's reagent (d) Benedict's solution
96. A  CH 2  C  O , Reactant ‘A’ in the reaction is (e) All of these
800 o C
[RPMT 2003] 107. Aldehyde turns pink with [Bihar MEE 1997]
(a) Benedict solution (b) Schiff reagent
(a) CH 3 CH 2 CHO (b) CH 3 CHO
(c) Fehling solution (d) Tollen's reagent
(c) CH 3  C  CH 3 (d) C2 H 5 OH (e) Mollisch reagent
||
O 108. Which of the following would undergo aldol condensation
97. Only an aldehyde having..... can undergo the aldol condensation [KCET 1998] [MP PMT 1986; BHU 1995]
(a) At least one beta H atom CH 3
|
(b) At least one alpha H atom (a) CCl 3 .CHO (b) CH 3  C  CHO
(c) An aromatic ring |
(d) No alpha H atom CH 3
98. Clemenson’s reduction of ketones is carried out in (c) CH 3 .CH 2 .CHO (d) HCHO
[BHU 2000]
109. The reaction of acetaldehyde with conc. KMnO4 gives
(a) H 2 with Pd catalyst (b) Glycol with KOH
[DPMT 1982; AIIMS 1996]
(c) LiAlH4 in water (d) Zn  Hg with HCl
(a) CH 3 COOH (b) CH 3 CH 2OH
99. Reaction
(c) HCHO (d) CH 3 OH
R R H
C  O   
H 2 NNH 2
C  N 2  H 2 is called 110. When acetaldehyde is heated with Tollen's reagent, following is
R KOH / glycol R H obtained [CPMT 1989; MP PET/PMT 1988]
[MP PET 2003] (a) Methyl alcohol (b) Silver acetate
(a) Wolff–Kishner reaction (b) Tischenko reaction (c) Silver mirror (d) Formaldehyde
(c) Reformatsky reaction (d) Gattermann reaction
111. Boiling point of acetone is [CPMT 1975, 89]
100. Propanal on treatment with dilute sodium hydroxide forms
[Kerala CET 2000] (a) 56 o C (b) 60 o C
(a) CH 3CH 2CH 2CH 2CH 2CHO
(c) 100 o C (d) 90 o C
(b) CH 3CH 2CH (OH)CH 2CH 2CHO 112. Urotropine is
(c) CH 3CH 2CH (OH)CH (CH 3 )CHO (a) Hexamethylene tetramine
(d) CH 3CH 2COONa (b) Hexaethylene tetramine
(c) Hexamethylene diamine
101. Identify the product Y in the sequence
H 2O / H 
(d) None of these
CH 3 CHO  CH 3 Mgl  X 
 Y
Ether
113. Magenta is [DPMT 1982; Kurukshetra CEE 1998]
[Kerala (Med.) 2001]
(a) Alkaline phenolphthalein
(a) CH 3 OH (b) CH 3 CH 2 OH (b) Methyl red
(c) (CH 3 )2 CHOH (d) (CH 3 )3 COH (c) p-rosaniline hydrochloride
102. What is the name of reaction when benzaldehyde changes into (d) Red litmus
benzyl alcohol [CPMT 1996; RPET 1999] 114. An aldehyde on oxidation gives [CPMT 1973, 03;
(a) Friedel-Craft's reaction (b) Kolbe's reaction DPMT 1983; Manipal MEE 1995]
(c) Wurtz reaction (d) Cannizzaro reaction
(a) An alcohol (b) An acid
103. The reagent that gives an orange coloured precipitate with
acetaldehyde (c) A ketone (d) An ether
[EAMCET 1997; Pb. PMT 2004; AIIMS 1987] 115. The reaction of an aldehyde with hydroxylamine gives a product
(a) NH 2OH (b) NaHSO 3 which is called [MP PET 1993; AFMC 2002]
(a) Aminohydroxide (b) Hydrazone
(c) Iodine (d) 2, 4-DNP
104. Which one is used in the manufacture of mirror (c) Semicarbazone (d) Oxime
[MP PET 1992] 116. Cannizzaro reaction is not shown by
(a) Red lead (litharge) [BHU 1980; IIT 1983; KCET 1993; Bihar MEE 1995;
(b) Ammoniacal AgNO3 RPMT 1997, 2000, 02]

(c) Ammoniacal AgNO3  Red lead (a) HCHO (b) C 6 H 5 CHO

(d) Ammoniacal AgNO3  HCHO (c) CH 3 CHO (d) All of these

105. When CH 3 COCH 3 reacts with Cl 2 and NaOH, which of the 117. When acetone is heated with hydroxylamine, the compound formed
is [MP PMT 1993]
following is formed [CPMT 1996]
(a) Cyanohydrin (b) Oxime
(a) CHCl 3 (b) CCl 4
(c) Semicarbazone (d) Hydrazone
(c) CCl 2 H 2 (d) CH 3 Cl 118. The product of the reaction between ammonia and formaldehyde is
106. Which gives difference between aldehyde and ketone (a) Urotropine (b) Formamide
[CPMT 1994]
(c) Paraformaldehyde (d) Methanol
119. Which of the following products is obtained by the oxidation of (c) Propanal (d) Butanal
propionaldehyde [CPMT 1989] 130. Schiff's reagent is [MP PMT 1989]
(a) Acetic acid (a) Magenta colour solution decolourised with sulphurous acid
(b) Formic acid and acetic acid (b) Ammoniacal cobalt chloride solution
(c) Propanoic acid (c) Ammoniacal manganese sulphate solution
(d) n-propyl alcohol (d) Magenta solution decolourised with chlorine
120. When acetaldehyde reacts with PCl5 , the resulting compound is 131. Pyrolysis[MP
of PMT 1992,gives
acetone 93] CH  C  O called
2
(a) Ethyl chloride (b) Ethylene chloride (a) Methylene oxide
(c) Ethylidene chloride (d) Trichloro acetaldehyde (b) Methyl carbon monoxide
121. Benzaldehyde and acetaldehyde can be differentiated by (c) Ketene
(a) HCN (b) NH 2 OH (d) Methone
(c) Hydrazine (d) NaOH solution 132. Which one of the following on oxidation will not give a carboxylic
acid with the same number of carbon atoms
122. In the presence of a dilute base C 6 H 5 CHO and CH 3 CHO
[CBSE PMT 1992; MP PET 1996]
react together to give a product. The product is
(a) CH 3 COCH 3 (b) CCl 3 CH 2 CHO
[MP PET 1994]
(a) C 6 H 5 CH 3 (b) C 6 H 5 CH 2 CH 2 OH (c) CH 3 CH 2 CH 2 OH (d) CH 3 CH 2CHO

(c) C 6 H 5 CH 2 OH (d) C 6 H 5 CH  CHCHO 133. Acetal is obtained by reacting in the presence of dry HCl and alcohol
with [MP PET 1996]
123. Grignard's reagent reacts with ethanal (acetaldehyde) and propanone to (a) Aldehyde (b) Ketone
give
(c) Ether (d) Carboxylic acid
(a) Higher aldehydes with ethanal and higher ketones with
propanone 134. The reagent with which both aldehyde and acetone react easily is[CPMT 1973, 74
(b) Primary alcohols with ethanal and secondary alcohols with (a) Fehling's reagent (b) Grignard reagent
propanone (c) Schiff's reagent (d) Tollen's reagent
(c) Ethers with ethanal and alcohols with propanone 135. Phenylmethanol can be prepared by reducing the benzaldehyde with
(d) Secondary alcohols with ethanal and tertiary alcohols with
(a) CH 3 Br (b) Zn and HCl
propanone
124. Base catalysed aldol condensation occurs with (c) CH 3 Br and Na (d) CH 3 I and Mg
[IIT-JEE 1991]
136. Which of the following is used in the manufacture of thermosetting
(a) Benzaldehyde plastics
(b) 2, 2-dimethyl propionaldehyde (a) Formaldehyde (b) Acetaldehyde
(c) Acetaldehyde (b) Acetone (d) Benzaldehyde
(d) Formaldehyde 137. Which compound undergoes iodoform reaction
125. Benzaldehyde reacts with ammonia to form [DPMT 1984; CPMT 1989]
[CPMT 1989; AFMC 1998]
(a) HCHO (b) CH 3 CHO
(a) Benzaldehyde ammonia
(b) Urotropine (c) CH 3 OH (d) CH 3 COOH
(c) Hydrobenzamide 138. Which does not react with Fehling solution [MNR 1983, 93]
(d) Aniline (a) Acetaldehyde (b) Benzaldehyde
126. Glucose + Tollen's reagent  Silver mirror shows (c) Glucose (d) Formic acid
[CPMT 1997] 139. Which of the following compound will react with ethanolic KCN
(a) Presence of acidic group (a) Ethane (b) Acetyl chloride
(b) Presence of alkaline group (c) Chlorobenzene (d) Benzaldehyde
(c) Presence of ketonic group 140. Schiff's reagent gives pink colour with
(d) Presence of aldehyde group [EAMCET 1980; MP PMT 2000]
127. Fehling solution is [MP PMT 1989] (a) Aldehydes (b) Ethers
(a) Ammoniacal cuprous chloride solution (c) Ketones (d) Carboxylic acid
(b) Acidified copper sulphate solution 141. Acetaldehyde reacts with Cl 2 (in excess) to give
(c) Copper sulphate and sodium hydroxide + Rochelle salt
[MP PMT 1997]
(d) None of these
(a) Chloral (b) Chloroform
128. Reduction of an aldehyde produces
(c) Acetic acid (d) Trichloroacetic acid
[MP PMT 1994; MP PET 2001]
142. The compound which reacts with Fehling solution is
(a) Primary alcohol (b) Monocarboxylic acid
[CPMT 1989]
(c) Secondary alcohol (d) Tertiary alcohol
129. Which of the following on reaction with conc. NaOH gives an (a) C6 H 5 COOH (b) HCOOH
alcohol [MP PET 1996] (c) C6 H 5 CHO (d) CH 2ClCH 3
(a) Methanal (b) Ethanal
143. Which one of the following undergoes reaction with 50% sodium (a) 1° > 3° > 2° (b) 1° > 2° > 3°
hydroxide solution to give the corresponding alcohol and acid (c) 3° [AIEEE
> 2° > 2004]
1° (d) 2° > 3° > 1°
(a) Butanal (b) Benzaldehyde 156. In Wolf-Kishner reduction, the carbonyl group of aldehydes and
(c) Phenol (d) Benzoic acid ketones is converted into [Pb. CET 2000]
144. Which one of the following is reduced with zinc and hydrochloric (a)  CH 2 group (b) CH 3 group
acid to give the corresponding hydrocarbon
[AIEEE 2004]
(c) CH 2 OH group (d)  CHOH group
(a) Acetamide (b) Acetic acid 157. Which of the following react with NaHSO 3
(c) Ethyl acetate (d) Butan–2–one [Pb. CET 2003]
145. Three molecules of acetone in the presence of dry HCl form (a) CH 3 COCH 3 (b) CH 3 CHO
[MP PET 2004]
(a) Mesitylene (b) Phorone (c) HCHO (d) All of these
(c) Glyoxal (d) Mesityl oxide 158. Fehling solution is [Pb. CET 2003]
146. Aldehydes and ketones can be reduced to corresponding (a) CuSO 4 + lime (b) CuSO 4  NaOH(aq)
hydrocarbons by [Kerala PMT 2004]
(c) CuSO 4  Na 2 CO 3 (d) None of these
(a) Refluxing with water
(b) Refluxing with strong acids 159. Wolf kishner reduction, reduces [Pb. CET 2003]
(c) Refluxing with soda amalgam and water (a) COOH group (b) C  C – group
(d) Refluxing with zinc amalgam and concentrated HCl (c) CHO group (d) O  group
(e) Passing the vapour under heated PbO2 160. A compound has a vapour density of 29. On warming an aqueous
147. Acetone reacts with iodine to form iodoform in the presence of solution of alkali, it[BHU
gives2004;
a yellow
CPMTprecipitate.
2004] The compound is
(a) CaCO 3 (b) NaOH (a) CH 3 CH 2 CHO (b) CH 3 CHOHCH 3

(c) KOH (d) MgCO3 (c) CH 3 COCH 3 (d) CH 3 CH 2 COOH

148. Cyanohydrin of which of the following forms lactic acid 161. Which responds to +ve iodoform test ? [Orissa JEE 2004]
[MHCET 2003] (a) Butanol (b) Butan-1-al
(a) CH 3 CH 2 CHO (b) CH 3 CHO (c) Butanol-2 (d) 3-pentanone
162. The correct order of reactivity of PhMgBr with
(c) HCHO (d) CH 3 COCH 3
[IIT-JEE (Screening) 2004]
149. Which of the following is used to detect aldehydes O O
O
[MHCET 2004] || || ||
(a) Million's test Ph  C  Ph CH 3  C  H CH 3  C  CH 3 is
(b) Tollen's reagent (I) (II) (III)
(c) Neutral ferric chloride solution (a) (I) > (II) > (III) (b) (III) > (II) > (I)
(d) Molisch's test (c) (II) > (III) > (I) (d) (I) > (III) > (II)
150. Which of the following aldehydes give red precipitate with Fehling 163. The pair of compounds in which both the compounds give positive
solution ? [MHCET 2004] test with Tollen's reagent is
(a) Benzaldehyde (b) Salicylaldehyde [IIT-JEE (Screening) 2004]
(c) Acetaldehyde (d) None of these (a) Glucose and Sucrose
151. A (CH 3 ) 2 C  CHCOCH 3 A is [MHCET 2004] (b) Fructose and Sucrose
(a) Acetone (b) Acetaldehyde (c) Acetophenone and Hexanal
(c) Propionaldehyde (d) Formaldehyde (d) Glucose and Fructose
152. The aldehyde which react with NaOH to produce an alcohol and 164. The most appropriate reagent to distinguish between acetaldehyde
sodium salt is [Pb. PMT 2004] and formaldehyde is [UPSEAT 2004]
(a) HCHO (b) CH 3 CHO (a) Fehling's solution
(b) Tollen's reagent
(c) CH 3 CH 2 CHO (d) CH 3 CH 2CH 2CHO
(c) Schiff's reagent
153. Acetaldehyde and Acetone can be distinguished by
(d) Iodine in presence of base
[DCE 2003]
165. Silver mirror test can be used to distinguish between
(a) Iododorm test
[MP PET 2004]
(b) Nitroprusside test
(a) Ketone and acid (b) Phenol and acid
(c) Fehling's solution test
(d) DNP test (c) Aldehyde and acid (d) Alcohol and phenol
 166. Paraldehyde is
154. OCH  CHO 
OH
 HOH 2 C  COOH [CPMT 1985; MP PET 1992, 96; RPMT 2000]
The reaction given is [DCE 2003] (a) A trimer of formaldehyde
(a) Aldol condensation (b) Knovengel reaction (b) A trimer of acetaldehyde
(c) Cannizzaro reaction (d) None of these (c) A hexamer of formaldehyde
155. The order of susceptibility of nucleophilic attack on aldehydes (d) A hexamer of acetaldehyde
follows the order [DCE 2002]
167. Paraldehyde is used as a [CBSE PMT 1989]
 (a) Medicine (b) Poison (b) 2-methyl propanal
(c) Polymer (d) Dye (c) p-methoxy benzaldehyde
168. Formalin is an aqueous solution of (d) 2,2 dimethyl propanal
[BHU 1979; DPMT 1983] (e) Formaldehyde
(a) Formic acid (b) Formaldehyde
(c) Fluorescein (d) Furfuraldehyde
169. Hexamethylene tetramine is used as [MP PMT 1979, 84]
(a) Analgesic (b) Antipyretic
(c) Urinary antiseptic (d) All of these
170. Methyl ketone group is identified by [BCECE 2005]
(a) Iodoform test (b) Fehling solution
1. Which of the following will fail to react with potassium dichromate
(c) Tollen’s reagent (d) Shiff’s reagent and dilute sulphuric acid
171. Which of the following does not give Fehling solution test? (a) Ethyl alcohol (ethanol)
[BCECE 2005] (b) Acetaldehyde (ethanal)
(a) Acetone (b) Propanal (c) Secondary propyl alcohol (2-propanol)
(c) Ethanal (d) Butanal (d) Acetone (propanone)
172. How will you convert butan2one to propanoic acid? 2. Acetone and acetaldehyde are differentiated by
[IIT 2005] [CPMT 1987, 93]
(a) Tollen’s reagent (b) Fehling’s solution (a) NaOH  I2 (b) Ag(NH 3 )2
(c) NaOH/I /H +
(d) NaOH/NaI/H +

2
(c) HNO 2 (d) I2
173. Ketones react with Mg-Hg over water gives [AFMC 2005]
3. Which of the following will react with water [IIT 1998]
(a) Pinacolone (b) Pinacols
(c) Alcohols (d) None of these (a) CHCl 3 (b) Cl 3 CCHO
174. Which of the following will form two isomers with semi carbazide[Orissa JEE 2005] (c) CCl 4 (d) ClCH 2 CH 2 Cl
(a) Benzaldehyde (b) Acetone
4. An organic compound ‘A’ has the molecular formula C 3 H 6 O, it
(c) Benzoquinone (d) Benzophenone
undergoes iodoform test. When saturated with dil. HCl is gives ‘B’
175. A compound A  C 5 H 10 Cl 2 on hydrolysis gives C 5 H 10 O of molecular formula C9 H 14 O . A and B respectively are [Tamil Nadu CET 2002
which reacts with NH 2 OH , forms iodoform but does not give (a) Propanal and mesitylene
fehling test. A is [DPMT 2005] (b) Propanone and mesityl oxide
Cl (c) Propanone and 2,6–dimethyl –2, 5-heptadien–4–one
|
(a) CH 3  C  CH 2  CH 2  CH 3 (d) Propanone and mesitylene oxide
| 5. Which alkene is formed from the following reaction
Cl
CH 3 CH 2 CH 2 CH  PPh3  2  Butanone [Manipal 2001]
Cl
| (a) 3- Methyl-3-heptene
(b) CH 3 CH 2  C  CH 2 CH 3 (b) 4-Methyl-3-heptene
|
Cl (c) 5-Methyl-3-heptene
Cl (d) 1-Methyl-5- methane
|
6. Compound ‘A’ (molecular formula C3 H 8 O) is treated with
(c) CH 3 CH 2 CH 2 CH 2 CH
| acidified potassium dichromate to form a product ‘B’ (molecular
Cl
formula C 3 H 6 O). ‘B’ forms a shining silver mirror on warming
Cl Cl with ammoniacal silver nitrate. ‘B’ when treated with an aqueous
| |
(d) CH 3  CH  CH  CH 2  CH 3 solution of H 2 NCONHNH 2 .HCl and sodium acetate gives a
product ‘C’. Identify the structure of ‘C’ [IIT-JEE (Screening) 2002]
176. CH 3  CHO  HCN  A ; Compound A on hydrolysis gives[Kerala CET 2005]
(a) CH 3CH 2CH  NNHCONH 2
(a) CH 3  CH 2  COOH
(b) CH 3  CH  NNH CONH 2
(b) CH 3  CH 2  CH 2  NH 2 |
CH 3
(c) CH 3  CO  COOH
(c) CH 3 CH  NCO NHNH 2
(d) CH 3 CO  CH  NOH |
CH 3
(e) CH 3  CH  COOH
|
OH (d) CH 3CH 2CH  NCONHNH 2
177. Which one does not give cannizzaro's reaction 7. Which is not true about acetophenone [Manipal 2002]
[Kerala CET 2005] (a) Reacts to form 2, 4-dinitorphenyl hydrazine
(a) Benzaldehyde (b) Reacts with Tollen’s reagent to form silver mirror
 (c) Reacts with I2 / NaOH to form iodoform

(d) On oxidation with alkaline KMnO4 followed by hydrolysis

gives benzoic acid (d)
8. The enol form of acetone, after treatment with D 2 O, gives
[IIT-JEE (Screening) 1999]
OD O 13. Among the given compounds, the most susceptible to nucleophilic
| || attack at the carbonyl group is [IIT 1997]
(a) CH 3  C  CH 2 (b) CD 3  C  CD 3
(a) MeCOCl (b) MeCHO
OH OD (c) MeCOOMe (d) MeCOOCOMe
| |
(c) CH 2  C  CH 2 D (d) CD 2  C  CD 14. Which of the following will give yellow precipitate with
9. The appropriate reagent for the transformation I 2 / NaOH [IIT 1997]
O
(a) ICH 2COCH 2CH 3
CH 2CH 3
CH 3 (b) CH 3 COOCOCH 3
HO HO (c) CH 3 CONH 2
[IIT-JEE (Screening) 2000]
(a) Zn(Hg), HCl (b) NH 2 NH 2 OH  (d) CH 3 CH (OH )CH 2 CH 3

(c) H 2 / Ni (d) NaBH 4 15. The product of acid hydrolysis of P and Q can be distinguished by [

10. Which of the following has the most acidic hydrogen

[IIT-JEE (Screening) 2000] OCOCH 3 H 3C
(a) 3-hexanone (b) 2, 4-hexanedione P  H 2C Q=
(c) 2, 5-hexanedione (d) 2, 3-hexanedione CH 3 OCOCH 3
(a) Lucas Reagent (b) 2,4-DNP
11. Which of the following will be most readily dehydrated in acidic
conditions [IIT-JEE (Screening) 2000] (c) Fehling’s Solution (d) NaHSO 3
16. On vigorous oxidation by permanganate solution
O OH OH
(a) (b) (CH 3 )2 C  CH  CH 2CH 2CH 3 gives [AIEEE 2002]

OH OH
(c) O (d) O | |
(a) CH 3  C  CH  CH 2 CH 3
|
CH 3
OH OH
12. CHO OHC CH 3
(i) NaOH / 100 o C (b) CHCO 2 H  CH 3 COOH

(ii) H  / H 2 O
CH 3
CHO OHC CH 3
Major Product is [IIT-JEE (Screening) 2003] (c) CHOH  CH 3 CH 2 CH 2 OH
COOH HOOC CH 3

(a) CH 3
(d) C  O  CH 3 CH 2 COOH
CH 3
COOH HOOC
HO HOOC 17. Which of the following reactions give benzo phenone
[Roorkee Qualifying 1998]
(b)
(a) 2C6 H 6  CCl 4  
(i) AlCl3
(ii)H 2 O

COOH HO
(b) C6 H 6  C6 H 5 COCl  
AlCl3
O
O
(c) o  CH 3 C 6 H 4 COC 6 H 5  
Heat
(c)
(d) o  HOOC  C 6 H 4  COC 6 H 5 

Cu
260 o C
O 18. Aldehyde and ketones can decolourize by [CPMT 2003]
O (a) Bromine water (b) Quick lime
CH OH HOH 2C
2

CH OH 2 HOH 2C
 (c) dil. H 2 SO 4 (d) None of these
19. Which of the following statements regarding chemical properties of H
acetophenone are wrong NCH 3
(a) (b)
(1) It is reduced to methyl phenyl carbinol by sodium and ethanol OH NCH 3
(2) It is oxidised to benzoic acid with acidified KMnO4 H
(3) It does not undergo iodoform electrophilic substitution like [Link] 3 H
nitration at meta position (c) (d) NCH 3
(4) It does not undergo iodoform reaction with iodine and alkali [Tamil Nadu CET 2001]
(a) 1 and 2 (b) 2 and 4 29. Products of the following reaction OH
(c) 3 and 4 (d) 1 and 3
CH 3 C  C CH 2 CH 3   ... are
(1) O 3
[CBSE PMT 2005]
20. The product(s) obtained via oxymercuration (HgSO4  H 2 SO 4 ) (2) Hydrolysis

of 1-butyne would be [IIT-JEE 1999] (a) CH 3 CHO  CH 3 CH 2CHO

(a) CH 3 CH 2 COCH 3 (b) CH 3 COOH  CH 3 CH 2 CHO
(b) CH 3 CH 2 CH 2 CHO (c) CH 3 COOH  HOOCCH 2 CH 3
(c) CH 3 CH 2 CHO  HCHO (d) CH 3 COOH  CO 2
(d) CH 3 CH 2 COOH  HCOOH 30. A compound, containing only carbon, hydrogen and oxygen, has a
molecular weight of 44. On complete oxidation it is converted into a
21. The most reactive compound towards formation of cyanohydrin on compound of molecular weight 60. The original compound is [KCET 2005]
treatment with KCN followed by acidification is [GATE 2001]
(a) An aldehyde (b) An acid
(a) Benzaldehyde (b) p-Nitrobenzaldehyde
(c) An alcohol (d) an ether
(c) Phenyl acetaldehyde (d) p-Hydroxybenzaldehyde
22. The key step in cannizzaro’s reaction is the intermolecular shift of [Orissa JEE 2003]
(a) Proton (b) Hydride ion
(c) Hydronium ion (d) Hydrogen bond
23. Benzophenone does not react with [BHU 2003]
(a) RNH 2 (b) SO 3
(c) NaOH (d) Na 2CO 3
Read the assertion and reason carefully to mark the correct option out of
24. The most suitable reagent for the conversion of
the options given below :
RCH 2 OH  RCHO is [AIIMS 2004]
(a) If both assertion and reason are true and the reason is the correct
(a) KMnO 4 explanation of the assertion.
(b) If both assertion and reason are true but reason is not the correct
(b) K 2 Cr2 O7 explanation of the assertion.
(c) CrO 3 (c) If assertion is true but reason is false.
(d) If the assertion and reason both are false.
(d) PCC (Pyridine chloro chromate)
(e) If assertion is false but reason is true.
25. The conversion of acetophenone to acetanilide is best accomplished
by using : [UPSEAT 2004]
1. Assertion : Acetic acid does not undergo haloform reaction.
(a) Backmann rearrangement
Reason : Acetic acid has no alpha hydrogens.
(b) Curtius rearrangement
[IIT 1998]
(c) Lossen rearrangement
2. Assertion : Benzonitrile is prepared by the reaction of
(d) Hofmann rearrangement chlorobenzene with potassium cyanide.
26. Which of the following will not give iodoform test ? Reason : Cyanide (CN ) is a strong nucleophile.
–

[UPSEAT 2004] [IIT 1998]

(a) Isopropyl alcohol (b) Ethanol 3. Assertion : Lower aldehyde and ketones are soluble in water
(c) Ethanal (d) Benzyl alcohol but the solubility decreases as molecular mass
increases.
Reason : Aldehydes and ketones can be distinguished by
27. MeO CHO  (X )  
CH 3 COONa
Tollen's reagent. [AIIMS 1994]
H3O
4. Assertion : Acetaldehyde on treatment with alkaline gives aldol.
Reason : Acetaldehyde molecules contains  hydrogen atom.[AIIMS 1997
CH  CHCOOH
5. Assertion : Acetylene on treatment with alkaline KMnO 4
The compound (X) is [IIT-JEE 2005]
produce acetaldehyde.
(a) CH 3 COOH (b) BrCH 2  COOH
Reason : Alkaline KMnO 4 is a reducing agent.
(c) (CH 3 CO ) 2 O (d) CHO  COOH
[AIIMS 2000]
28. The major organic product formed from the following reaction 6. [CBSE PMT
Assertion 2005]
: Acetophenone and benzophenone can be
distinguished by iodoform test.
O
  ... is
(i) CH 3 NH 2
(ii) LiAlH4 (iii) H 2 O
 Reason : Acetophenone and benzophenone both are carbonyl
compounds. [AIIMS 2002]
7. Assertion : Isobutanal does not give iodoform test
Reason : It does not have -hydrogen. [AIIMS 2004]
8. Assertion : Benzaldehyde is more reactive than ethanol towards
nucleophilic attack.
Reason : The overall effect of –I and +R effect of phenyl
group decreases the electron density on the carbon
atom of  C  O group in benzaldehyde.
9. Assertion : Aldol condensation can be catalysed both by acids
and bases.
Reason : -Hydroxy aldehydes or ketones readily undergo
acid catalysed dehydration.
10. Assertion : Ketones are less reactive than aldehydes.
Reason : Ketones do not give schiff's test.
11. Assertion : Oximes are less acidic than hydroxyl amine.
Reason : Oximes of aldehydes and ketones show geometrical
isomerism.
12. Assertion : The bond energy of  C  O is less than
> C  C < in alkenes.
Reason : The carbon atom in carbonyl group is sp 2
hybridised.
13. Assertion : R  C  0  is more stable than R  C   0 .
Reason : Resonance in carbonyl compound provides C and +

O. –

14. Assertion : Formaldehyde cannot be prepared by Rosenmund's

reduction.
Reason : Acid chlorides can be reduced into aldehydes with
hydrogen in boiling xylene using palladium or
platinum as a catalyst supported on barium
sulphate. This is known as Rosenmund's reduction.
15. Assertion : CH 3 CHO reacts with NH 3 to form urotropine.
Reason : Urotropine is used as medicine in case of urinary
troubles.
16. Assertion : -Hydrogen atoms in aldehydes and ketones are
acidic.
Reason : The anion left after the removal of -hydrogen is
stabilized by inductive effect.
17. Assertion : 2, 2–Dimethyl propanal undergoes Cannizzaro
reaction with concentrated NaOH.
Reason : Cannizzaro is a disproportionation reaction.
18. Assertion : Benzaldehyde undergoes aldol condensation.
Reason : Aldehydes that do not have –hydrogen undergo
aldol condensation.

Introduction

1 a 2 b 3 a 4 c 5 a
6 c 7 b 8 b 9 a 10 b
11 b 12 d 13 d 14 b 15 a
16 c 17 c 18 c
 Preparation 166 d 167 a 168 b 169 c 170 a
171 a 172 c 173 b 174 a 175 a
1 c 2 c 3 d 4 b 5 b,c 176 e 177 b
6 c 7 c 8 d 9 c 10 c
11 c 12 a 13 a 14 d 15 d Critical Thinking Questions
16 c 17 a 18 d 19 c 20 b
1 d 2 bc 3 b 4 c 5 a
21 c 22 a 23 c 24 c 25 c
6 a 7 b 8 b 9 b 10 b
26 d 27 c 28 b 29 a 30 b
11 a 12 b 13 a 14 a,d 15 c
31 c 32 d 33 b 34 b 35 a
16 d 17 b,d 18 d 19 c 20 a
36 d 37 d 38 c 39 b 40 c
21 b 22 b 23 d 24 d 25 a
41 d 42 a 43 a
26 d 27 c 28 b 29 c 30 a

Properties
Assertion & Reason
1 c 2 c 3 a 4 a 5 c
1 c 2 d 3 b 4 a 5 d
6 d 7 a 8 c 9 c 10 b
6 b 7 c 8 a 9 b 10 b
11 c 12 a 13 a 14 b 15 d
11 e 12 e 13 b 14 b 15 e
16 b 17 c 18 c 19 abd 20 abcd
16 c 17 b 18 d
21 b 22 a 23 a 24 b 25 d
26 b 27 d 28 c 29 b 30 b
31 c 32 c 33 d 34 d 35 c
36 b 37 a 38 b 39 d 40 c
41 d 42 a 43 d 44 d 45 a
46 c 47 c 48 a 49 b 50 b
51 b 52 c 53 d 54 b 55 c Introduction
56 d 57 c 58 a 59 c 60 c
O OH
61 b 62 b 63 a 64 b 65 a || |
1. (a) CH 3  C  H  HCN  CH 3  C  H (optically active)
66 d 67 a 68 a 69 c 70 a Acetaldehyde Hydrogen |
Cyanide
71 c 72 d 73 a 74 a 75 a CN
Acetaldehyde
76 d 77 c 78 b 79 a 80 b Cynohydrin

81 c 82 c 83 c 84 a 85 d 2. (b)  C  O
sp 2 hybridised
86 a 87 d 88 a 89 d 90 d
O
91 b 92 b 93 a 94 c 95 c ||
7. (b) CH 3 CCH 3
96 a 97 b 98 d 99 a 100 c 2 propanone
101 c 102 d 103 d 104 d 105 a 10. (b) CHOCHO
106 e 107 b 108 c 109 a 110 c  
R
111 a 112 a 113 c 114 b 115 d 11. (b) 
C O
R 
116 c 117 b 118 a 119 c 120 c
Cl O
121 d 122 d 123 d 124 c 125 c | ||
13. (d) Cl  C  C  H
126 d 127 c 128 a 129 a 130 a |
Cl
131 c 132 a 133 a 134 b 135 b 2, 2, 2, trichloroethanal

136 a 137 b 138 b 139 d 140 a 18. (c) Among Carbonyl Compounds, reactivity decrease with increase
in alkyl groups as alkyl groups (+I effect) decrease positive
141 a 142 b 143 b 144 d 145 b character on C-atom. Thus, the correct order of reactivity is
146 d 147 b 148 b 149 b 150 c HCHO  CH 3CHO  C6 H5 CHO
151 a 152 a 153 c 154 c 155 b
156 a 157 d 158 d 159 c 160 a
161 c 162 c 163 d 164 d 165 c Preparation
 42. (a)
HC  CH   CH 3 CHO  

1% HgSO CH MgX
1. (c) 4 3
20 % H 2 SO 4 ( A) H 2O

CH 3 CHOHCH 3  CH 3 COCH 3

[O ]

(B) Acetone
CH 3
4. (b) (CH 3 )2 C  C(CH 3 )2 
 2CH 3  CO  CH 3
O3 |
43. (a) C 9 H 18  O 3  H 3 C  C  CHO  CH 3 CH 2 COCH 3
(c) Ketonic hydrolysis: CH 3  CO  CH 2COOC 2 H 5
| 2  butanone
5. CH 3
2, 2 dimethyl propanal
  CH 3 COCH 3  C2 H 5 OH  CO 2
NaOH
H 2O On the basis of product formation, it would be alkene
COCH 3
CH 3 CH 3
 CH 3 COCl  
AlCl | |
6. (c) 3
+HCl
CH 3  C  HC  C  CH 2 CH 3
It is Friedel-Crafts reaction. Acetophenone |
CH 3
9. (c) CH 3 COCl 
 CH 3 CHO  HCl 2H
2, 2, 4  trimethyl- 3 - hexene
Pd / BaSO 4
CH 3
CHO CH 3 CH 3
| |
10. (c) 
CrO 2 Cl 2
Etard reaction CH 3  C  HC  C  CH 2 CH 3 

O3

|
CH 3
CH 3 COCH 3  (CH 3 )3 COH
CH 3 MgI
11. (c)
Acetone tert  Butyl alcohol CH 3 O CH 3
| |
13. (a) It is hydration of alkynes.
CH 3 C — HC CCH 2 CH 3
O | | |
Hg  
|| CH 3 O O
CH 3  CH 2  C  CH  CH 3  CH 2  C  CH 3
H 2O Butanone
CH 3 O
O | ||
||  CH 3 C  CHO  CH 3 C  CH 2 CH 3
CH 3  C  O |
14. (d) Ca CH 3
CH 3  C  O   CH 3  CO  CH 3  CaCO 3
Dry heating
||
Acetone
O Properties
COCH 3

1. (c) CH 3 COCH 3  CH 3 MgCl  (CH 3 )3 C  OMgCl

16. (c)  CH 3 COCl   
only AlCl3
 HCl (X)


(CH 3 )3 C  OH  Mg(OH )Cl
hydrolysis
(Y )
CH 3 COO OOCH Distill
18. (d) Ca  Ca  2. (c) It is cannizzaro reaction –2
CH 3 COO OOCH
CHO COO  CH 2OH
2CH 3 CHO  2CaCO 3
19. (c) CH 3  C  N  C H 3 Mg Br  CH 3  C  N  MgBr  
KOH
+
| 
CH 3 Cl Cl Cl
Hydrolysis OH
Br |
CH 3  CO  CH 3  NH 3  Mg
OH 3. (a) R  CO  R '   R  C  R ' 
HCN

LiAlH4

|
O CN
|| ( A)
CH 3  CH  CH 2  CH 3  CH 3  C  CH 2 CH 3
KMnO 4
23. (c)
| Oxidation ethyl methyl ketone OH
OH |
2  Butanol
CH 3
CHO COOH R  C  CH 2 NH 2
CH 3 CH 3 |
R'
24. (c)  
CrO 2Cl 2
 
acidic K 2 Cr2 O7
or KMnO 4
5. (c) Reduction of  C  O to CH 2 can be carried out with Wolf
This is Etard’s reaction Kischner reduction.
R R CHO CH 2OH
32. (d) CH  OH  
[(CH 3 )3 CO ]3 Al
CO
R Aluminium ter butoxide R
Isopropyl alcohol Ketone
6. (d) 
2H

34. (b) HC  CH  H 2 O 

 CH 3 CHO HgSO 4 / H 2 SO 4
Benzaldehyde Benzylalcohol
on reduction it gives benzylalcohol and not phenol.
5 7 7
2 6 CH 5
6 CH
43 1 3
4
3

C=O
6 
ozonolysis
3
HC=O
34 1 1
5 2
2 6-oxoheptanal
9. (c) C6 H 5 CHOHCH 3  C6 H 5 COCH 3
[O ] O O
|| ||
1  Phenyletha nol Acetopheno ne
30. (b) CH 3  C  CH 3  3 I 2  NaOH  CHI 3  CH 3  C  ONa
C6 H 6  CH 3 COCl    C6 H 5 COCH 3  HCl
Friedel craft's dimethyl ketone
reaction

10. (b) Wolf-Kishner reduction does not convert  CO to CHOH 31. (c) CHI 3 is yellow compound when iodine reacts with NaOH
but converts it to  CH 2 . and ketone.
11. (c) Although both CH 3 CH 2COCH 3 and (CH 3 )3 CCOCH 3 32. (c) HCHO  HCHO   HCOOK  CH 3 OH
KOH

contain -hydrogen, yet (CH 3 )3 CCOCH 3 does not undergo

Aldol condensation due to steric hindrance. CHO COONa CH 3 OH
12. (a) C 6 H 5 CHO    C 6 H 5 CH (OH )CH 3
CH 3 MgBr CH 3
Benzaldehyde H  / H 2O 2 Alcohol 38. (b) 2  
Conc. NaOH
+
13. (a) Chloral CCl 3 CHO, has no -hydrogen atom and hence does
not undergo aldol condensation. This reaction is called as Cannizzaro’s reaction.
14. (b) Among the given compounds only acetone gives crystalline
coloured derivative with 2, 4 DNP.
15. (d) Ethanal among the given compounds gives positive iodoform CHO CHO COOK CH 3 OH
test. CH 3 CH 3 Conc .
39. (d) +  +
OH KOH
| Cl Cl Cl Cl
17. (c) 2CH 3 CHO 
 CH 3  CH  CH 2 CHO
dil.
NaOH
41. (d) The solution represented is fehling’s and it has no tendency to
18. (c) C2 H 5 CHO  2Cu 2  5 OH   Cu 2 O  3 H 2 O oxidise benzaldehyde.
Re d ppt
42. (a) Increasing alkyl group the reactivity decreases.
 C2 H 5 COO  1
43. (d) RCHO  O2  RCOOH
CH 3 COCH 3  2Cu 2  5 OH   No reaction 2
44. (d) All test for Aldehyde because ketone require strong oxidising
19. (abd)Deuterium behaves like H and hence trideuteroacetaldehyde agent.
also undergoes aldol condensation but benzaldehyde does not
since it has no -hydrogen. 2[ Ag(NH 3 )2 ]  RCHO  RCOOH  2 Ag  4 NH 3  H 2O
21. (b) 1o Primary alcohol  
ZnCl 2 / HCl 45. (a) Silver mirror test is the test of aldehyde.
White turbidity only heating 46. (c) CH 3 CH  CHCHO  2[ Ag(NH 3 )2 ] 
2 o Alcohol   White turbidity
ZnCl 2 / HCl
2 Ag  4 NH 3  CH 3CH  CHCOOH  H 2O
after 5 min heating
OH
3 o Alcohol  easily in seconds
ZnCl 2 / HCl |
49. (b) CH 3  C  H  NH 3  CH 3  C  H
24. (b) Benzaldehyde on treatment with 50% aqueous or ethanolic || |

alkali solution undergoes Cannizzaro’s reaction like HCHO O NH 2

(no  -hydrogen atom) i.e., one molecule is oxidised and one is OCH 3
reduced with the formation of benzoic acid and benzyl alcohol || |
respectively. 2CH 3  C  CH 3  NH 3  CH 3  C  CH 2  C  CH 3
|| |
2C 6 H 5 CHO   C 6 H 5 CH 2 OH  C 6 H 5 COONa
NaOH
O NH 2
25. (d) 2 HCHO 
 CH 3 OH  HCOONa
NaOH
50. (b) CH 3 CHO  2 H 
 CH 3 CH 2 OH
Na / C2 H5 OH
Conc .
It is a Cannizzaro’s reaction. 51. (b) CH 3 CH 2 CHO  4 H    CH 3 CH 2 CH 3  H 2 O
Zn / Hg
HCl
OH
| This reaction is called clemmenson’s reduction.
2CH 3 CHO   CH 3  CH  CH 2  CHO
NaOH
52. (c) In cannizaro’s reaction the one substance is oxidized and other
dil
is reduced.
It is aldol condensation reaction.
HCHO  HCHO   CH 3 OH  HCOOK
KOH
O O
|| || 55. (c) Nucleophilic as addition of HCN , NaHSO 3 etc.
27. (d) CH 3  CH 2  C  CH 2  CH 3 do not have CH 3  C  57. (c) Addition of HCN to carbonyl compounds is an example of
nucleophilic addition.
group 58. (a) Acetone forms sodium bisulphate adduct but acetophenone
O O does not. Aromatic ketones do not gives addition product with
|| || NaHSO 3 .
29. (b) CH 3  C  CH 3  3 Cl2  CH 3  C  CCl 3  3 HCl
59. (c) C 6 H 5 CHO  Cl 2  C 6 H 5 COCl  HCl
Benzaldehyde Benzoyl chloride
O O
|| || 
CH 3  C  CCl 3  NaOH  CHCl 3  CH 3  C  ONa 60. (c) CH 3  O  CH 3 The electron density of oxygen is highly

increased therefore resistant its nucleophilic attack.
 CH 3 CH 3 R R CN
| | 83. (c) C  O  HCN  C is an example of
63. (a) 2CH 3  CO  CH 3  H 3 C  C  Mg / Hg
C  CH 3
Acetone H 2O
| | R R OH
OH OH nucleophilic addition reaction.
(Pinacol )
84. (a) C6 H 5 CHO  CH 3 COC6 H 5  
NaOH
 H 2O
64. (b) C6 H 5 CHO  (CH 3 CO )2 O  CH 3 CO 2 Na

C6 H5 CH  CHCO 2 H O
||
It is Perkin’s reaction. C6 H 5  CH  CH  C  C6 H 5
65. (a) Crossed aldol reaction gives benzyl alcohol and sodium Benzyl acetopheno ne
formate.
85. (d) HI/P/, Zn/Hg/conc. HCl and
C6 H 5 CHO  HCHO   
NaOH (aq )

Benzaldehyde Formaldehy de NH 2  NH 2 / OH  / C2 H 5 ONa

C6 H 5 CH 2OH  HCOONa O
Benzyl alcohol Sod. formate ||
66. (d) The substitution of alkoxy group of ester by an alcohol, is used to the reduction of  C  group into CH 2  group.
called trans-esterification. It occurs in presence of either an
acid or base.
CH 3
67. (a) 6 HCHO  4 NH 3  (CH 2 )6 N 4  6 H 2 O 86. (a) 3CH 3 COCH 3   
Conc . H 2 SO 4
Urotropine 3 H 2O

68. (a) In HCHO because -Hydrogen atom is absent.

O O H3C CH 3
|| ||
71. (c) C 6 H 5  C  H  H  C  C 6 H 5  
alc NaCN
87. (Mesitylene)
(d) 2C6 H 5 CHO  C6 H 5 COONa  C6 H 5 CH 2OH
50 % NaOH

It is Cannizzaro’s reaction.
OH O 88. (a) Because acetone require stronger oxidising agent and hence not
| ||
C6 H 5  CH  C  C6 H 5 oxidized with Fehling solution to give brick red ppt.
Benzoin 89. (d) CH 3 CHO   CH 3 COOH  Ag   NH 3
[ Ag( NH 3 )2 ]

O Silver mirror test

||
NH 2  NH 2 While acetone do not react.
72. (d) CH 3  C  CH 3 
KOH / Glycol 90. (d) Due to H  bonding all are soluble in water.
CH 3  CH 2  CH 3  H 2 O  N 2 CH 3
|
75. (a) 2CH 3 CHO   CH 3  CH  CH 2  CHO
NaOH
91. (b) CH 3  C  O  CH 3 MgBr  CH 3  C  OH
dil | | |
OH H H
(Aldol)
( 2 o alcohol)
76. (d) The amount of enolic form is highest (76%) in acetyl acetone

because keto group is a much better electron-withdrawing 92. (b) CH 3 CHO   CH 3 CH (OH ) CN 
HCN

2 H 2O / H
group.
CH 3 CH (OH ) COOH
O O O — H . . . .O
|| || | || 93. (a) This reaction is aldol condensation
CH 3 CCH 2 CCH 3 ⇌ CH 3 C  CH  CCH 3 2CH 3 CHO    CH 3  CH  CH 2  CHO
dil NaOH
acetyl acetone enolic form (76%) |
(keto form, 24%)
OH
3  hydroxy butanal
O .... H — O
|| | 94. (c) HCHO  2Cu 2  5 OH     HCOO   Cu 2 O  3 H 2 O
Fehling

 CH 3 C  CH  C  CH 3 solution Red ppt

CHO COONa CH OH OH
2 95. (c) H  CHO  CH 3 MgI  CH 3  CH 2  OH  Mg
I
78. (b)  
NaOH
+ O
||  
100. (c) CH 3 CH 2  C   H CH  CHO 
OH

| |
H
| CH  CH  CHO H CH 3
80. (b) C  O  H 2 CH .CHO  Cinnamalde hyde
OH
|
CH 3  CH 2  CH  CHCHO
82. (c) CH 3 CHO 
 CH 3  CH  CH 2  CHO
dil NaOH |
| CH 3
OH
Aldol
 OMgI 
 | 
 CH 3  CH  CH  CHO  H 2O
Heat
101. (c) CH 3 MgI  CH 3 CHO  CH 3  C  H 
 |

 CH 3 
 
 
H3O
 (CH 3 )2 CHOH Cl
120. (c) CH 3  CHO  PCl5  CH 3  CH  POCl3
2  Propanol Cl
102. (d) Cannizzaro’s reaction involve self oxidation and self reduction. Ethylidene Chloride
or
Gem dihalide
NO 2
121. (d) Benzaldehyde gives cannizaro’s reaction whereas acetaldehyde
gives aldol condensation.
103. (a) CH 3CHO  NH 2 NH NO  2

CHO COONa CH OH
2

Brady’s reagent (2, 4 – DNP)

NO
2  
Conc NaOH
+
2

CH 3CH  N  NH NO Cannizaro reaction

2
2CH 3 CHO    CH 3  CH  CH 2  CHO
dil NaOH
|
Orange crystalline solid OH
105. (a) 2CH 3COCH 3  Cl2 / NaOH  2CHCl 3 + ( Aldol)

2CH 3COONa  HCl O H OH H

|| | | |
106. (e) Fehling solution  Alkaline CuSO 4  Na  K tartarate 122. (d) C  CH 2  CHO  C — CH  CHO
| |
Tollen’s reagent  NH 4 OH  AgNO3
H H
Schiff’s reagent  P-rosaniline hydrochloride or magneta
Benedict’s solution  Alkaline CuSO 4  Citrate ions  CH  CH  CHO
Cinnamalde hyde
All these reagents are used to distinguish between aldehydes O
and ketones. Aldehydes reacts with all these reagents while ||
ketones do not react. 123. (d) CH 3  MgBr  CH 3  C  H  
H 2O

107. (b) Schiff' s reagent   Colourless

SO 2
CH 3  CH  OH  MgBr(OH )
(Pink) |
CH 3
 Pink colour
Aldehyde
CH 3 MgBr  CH 3  C  O  
H 2O

 
|

108. (c) CH 3  CH 2  CHO aldehydes having   H atom can CH 3

participate in aldol condensation. The H  atom attached to CH 3 CH 3

 carbon atom are called  -hydrogen. C  MgBr(OH )
109. (a) CH 3 CHO  CH 3 COOH
KMnO 4 OH CH 3
Oxidation
Acetaldehyde Acetic acid
C 6 H 5 CH  N
110. (c) CH 3 CHO  2[ Ag(NH 3 )2 ]OH  125. (c) 3 C 6 H 5 CHO  2 NH 3  CH  C 6 H 5  3 H 2 O
Tollen's reagent
C 6 H 5 CH  N
CH 3 COONH 4  2 Ag  3 NH 3  H 2O Hydrobenza mide
Silver mirror 127. (c) CuSO 4  NaOH  Roschellesalt(Na  K tartarate )
112. (a) It is used as a medicine to treat urinary infections.
128. (a) R  CHO    R  CH 2  OH
Reduction
113. (c) p-rosaniline hydrochloride. Aldehyde
1o alcohol
CH 3
129. (a) HCHO  HCHO 
 CH 3 OH  HCOONa
NaOH
Conc
NH 2  131. (c) CH 3  CO  CH 3   CH 2  C  O
Pyrolysis

C  NH 2 Cl  Acetone Ketene

NH 2 O
||
CH 3  C  CH 3 2 2 
  CH 3 COOH  HCOOH
K Cr O
132. (a) 7
H 2 SO 4

It is used for the identification of aldehydes. one carbon atom is less in the ketone group
H 2 N OH R
115. (d) R  CHO    RCH  N  OH |
Oxime
134. (b) R  C  O  R  Mg  X  R  C  OMgX
CH 3 CHO  NH 2OH  CH 3  CH  N  OH  H 2O | Grignard reagent |
Acetaldoxime H
H
116. (c) Cannizzaro’s reaction is shown by aldehydes in which -H Aldehyde
atom is absent. CH 3 CHO contains 3,  -H atoms thus, does R
not show this reaction. |
CH 3 CH 3 R  C  O  R  Mg  X  R  C  O  MgX
117. (b) C  O  NH 2 OH  C  N  OH  H 2O | |
CH 3 CH 3 Acetoxime R R
Ketone
119. (c) CH 3  CH 2  CHO    CH 3 CH 2  COOH
Oxidation

Propanal Propanoic acid

137. (b) CH 3 CHO   CHI 3
NaOH 151. (a) Two molecules of acetone condense in presence of dry HCl gas
I2 Yellowppt to form mesityl oxide.
138. (b) Fehling solution is a weak oxidising agent therefore unable to O
CH 3 ||
oxidise benzaldehyde. C  O  H 2  CH  C  CH 3  
HCl
CH 3  H 2O
O O OH O
| | | |
(CH 3 )2 C  CH .COCH 3
H–C H–C CH – C Mesityl oxide
152. (a) Formaldehyde and NaOH reacts to produce alcohol and sodium
139. (d) salt of an acid.
+  
Alc. KCN
2 HCHO  NaOH  CH 3 OH  HCOONa
Benzoin
This reaction is called benzoin condensation. Alcohol Sodium formate

140. (a) Aldehyde  Schiff' s reagent  Pink colour This reaction is Cannizzaro's reaction
(Colourless) 153. (c) Acetaldehyde reduces Fehling solution giving red ppt. while
Ketone do not give this test. acetone do not.
154. (c) It is an example of Cannizzaro reaction
CH 3 CHO 
  CCl 3 CHO  3 HCl
Cl
141. (a) 2
CH 2 OH
(Choral ) CHO
|  NaOH  |
143. (b) Benzaldehyde will undergo Cannizzaro's reaction on treatment CHO COONa
with 50% NaOH to produce benzyl alcohol and benzoic acid as 
it does not contain -hydrogen 155. (b) R  C  H ; Susceptibility of nucleophilic attack on aldehyde
||
CHO CH 2 OH COONa O
 
50% NaOH is decreased by electron releasing effect of R group. Decreasing
order of aldehyde towards nucleophilic attack is 1° > 2° > 3° R
+ group.
Benzaldehyde Benzyl 156. (a) Wolf kischner reduction : Hydrazine (NH 2  NH 2 ) followed
Sodium Benzoate
144. alcohol
(d) Butane 2-one will get reduced into butane when treated with Zinc by reaction with strong base like KOH reduce carbonyl group
and hydrochloric acid following Clemmensen reduction, whereas into alkyl group.
Zn/HCl do not reduce ester, acid, amide C  O  NH 2  NH 2  
Wolf- Kishner

145. (b) Phoron Carbonyl group Hydrazine reduction

O
||
C  N  NH 2   CH 2
KOH
CH 3 CH 3
C  O  H 2 CH  C  CHH 2  O  C Alkyl group
CH 3 CH 3 157. (d) Ketones and Aldehyde add to NaHSO 3 to give white
O precipitate
CH 3 || CH 3 R R OH
 
Dry HCl
C  CH  C  CH  C C  O  
NaHSO 3
C
 2 H 2O CH 3 Phoron CH 3 R R SO 3 Na
Zn  Hg / HCl
146. (d) RCHO  4 H    R  CH 3  H 2 O 158. (d) Fehling's solution is the solution of CuSO 4  NaOH +
R Zn  Hg / HCl R Roschel salt (Sodium potassium tartarate). Aldehyde give red
C  O  4 H    CH 2  H 2 O precipitate with Fehling's solution.
R R
147. (b) Acetone on iodination gives iodoform in the presence of NaOH 159. (c) It reduce CHO group into hydrocarbon.
O 160. (a) Molecular weight of the compound
||
 3 H 2O
CH 3  C  CH 3  3 I2  4 NaOH    2  Vapour density
Acetone
 2  29  58
CHI 3  CH 3 COONa  3 NaI
Iodoform Sodium acetate Sodium iodide Molecular weight of CH 3 CH 2CHO, CH 3 CHOHCH 3 ,
148. (b) We know that CH 3 COCH 3 and CH 3 CH 2COOH are 58, 60, 58 and 74
H H
| | respectively. Both CH 3 CH 2CHO and CH 3 COCH 3 have
 HCN
 H 2O
CH 3  C  O 
 CH 3  C  OH   molecular weight 58 but only aldehyde i.e., CH 3 CH 2CHO
Acetaldehyde |
CN on warming with aqueous alkali gives yellow precipitate.
Cyanohydri n
OH OH
H | |
|
161. (c) CH 3  CH 2  CH  CH 3 contain CH 3  CH  group by
CH 3  C  OH 2 butanol
|
COOH which it give +ve iodoform test.
Lacticacid 162. (c) In nucleophilic addition reaction, the carbonyl compound will
Thus Lactic acid is formed. respond in preference which is sterically more exposed and
149. (b) Tollen's reagent is used to detect aldehydes. Aldehyde reduce electronically have intact positive charge over carbonyl carbon.
Tollen's reagent to give Silver mirror while these are oxidised So reactivity order towards reaction with phMgBr is (II) > (III)
to acid. > (I).
R 163. (d) Tollen's reagent oxidizes the compound having aldehyde group
C  O  Ag 2 O  RCOOH  2 Ag
H Silver mirror like glucose and also oxidizes -hydroxy ketones having
150. (c) Only aliphatic aldehyde reduce fehling solution. Hence, COCH 2OH group as in fructose.
acetaldehyde give red ppt. with fehling solution.
164. (d) Acetaldehyde have CH 3 CO  group so it give positive OH Cl
| |
iodoform test with I2 and NaOH while formaldehyde does not CH 3  C  CH 2 CH 2 CH 3  CH 3 C  CH 2 CH 2 CH 3
H 2O

have CH 3 CO group so it will not give the positive | |

OH Cl
haloform test.
OH
165. (c) Aldehyde reduce silver mirror whereas acid do not reduce silver | 
mirror. 176. (e) CH 3 CHO  HCN  CH 3 C  C  CN  

H 3O

|
CH 3 OH
|
(A)
CH
OH
O O |
166. (d) 3 CH 3 CHO   
conc. H 2 SO 4
CH 3  C  COOH
room temp. CH CH |
H
CH 3 O CH 3
Paraldehyd e 177. (b) Aldehyde, which does not have the   H atom, gives
cannizzaro's reaction on heating with conc. alkali solution
168. (b) Formaline contains 40% HCHO, 8% CH 3 OH and 52%
(50%)
water. It is used as biological preservative. OCH 3
172. (c) C 2 H 5  C  CH 3  I2  NaOH  C 2 H 5 CO 2 Na   CHI 3 CH 3
|| |
O C6 H 5 CHO CH 3  CHCHO
  H atom absent   H - atom

C2 H 5 CO 2 Na  H
 C2 H 5 COOH  Na 
CHO
173. (b) Two molecules of ketones undergo reduction in the presence of   H - atom absent
Mg / Hg to form pinacol. CH 3
  |

  CH 3 C  CHO HCHO
CH 3 CH 3   H  atom absent
 | |  |
CH 3 CH 3
2 C  O   CH 3  C — C  CH 3 
Mg / Hg
  H - atom absent
CH 3 benzene as  | |

acetone
solvent  
 O O 
 Mg 
CH 3 CH 3
| |
Critical Thinking Questions
  CH 3 
HOH
C  C  CH 3  Mg(OH )2
| |
OH OH 1. (d) Acetone oxidise by K 2 Cr2 O7 & conc. H 2 SO 4 into
2, 3  dimethylbutane  2, 3  diol
(pinacol) carboxylic acid. It is not oxidised by dilute H 2 SO 4 .
174. (a) C6 H 5 CH  O  H 2 NNHCONH 2 2. (b) Acetaldehyde react with tollen's reagent while ketone do not
react with tollen's reagent.
 C6 H 5 CH  NNHCONH 2
semicarbazone 3. (b) CCl 3  CHO  H 2O  CCl 3 .CHO.H 2O 
(Chloral hydrate )
The product shows E and Z configuration
OH
CH H CCl 3 .CH
CH
6 5 H
6 5

OH
C
C
4. (c) The compound A with formula C3 H 6 O gives iodoform test, it
N is propanone forms a compound B having carbon atoms three
N
.. times, the number of carbon atoms in propanone, it is 2, 6-
.. NHCONH 2
H NCOHN
2 dimethyl-2, 5-heptadien-4-one.
Z-
E- CH 3
175. (a) As A reacts with hydroxylamine it means A may be |

aldehyde or ketone. but it does not react with fehling solution 5. (a) CH 3 CH 2  C  O  CH 3 CH 2 CH 2 CH  PPh3
2  Butanone
hence A must be a ketone. Secondly it forms iodoform which
is a characteristic reaction of methyl ketone. CH 3
|
O NOH  CH 3 CH 2 C  CHCH 2CH 2CH 3  Ph3 PO
|| || 3  methyl, 3  heptene
CH 3 C  CH 2 CH 2 CH 3   CH 3 C  CH 2 CH 2 CH 3
NH 2OH

6. (a) CH 3  CH 2  CH 2OH  CH 3  CH 2  CHO

[O ]
I2 / NaOH (A) (B)

H 2O CHI 3 H
|
CH 3  CH 2  C  O  H 2 NNHCONH 2 
HCl
 CH 3CH 2CH  N  NHCONH 2
7. (b) Acetophenone is a ketone and does not react with Tollen’s
reagent to give silver mirror.
O  OH 
||  | 
8. (b) CH 3  C  CH 3 CH 3  C  CH 2  ⇌
Acetone (ketoform)  enol form 
  13. (a) Amongst aldehyde & the acid derivatives, acid chloride are the
most susceptible to nucleophilic attack due to strong –I effect
OD O & weak +R effect of the Cl-atom as a result of which carbonyl
| || carbon has the highest electron deficiency. The actual order is
CH 3  C  CH 2 ⇌ CH 3  C  CH 2 D MeCOCl >MeCOOCOMe >MeCOOMe >MeCHO.
OH OD 14. (ad) ICH 2COCH 2CH 3    CHI3  CH 3 CH 2COONa
I2 / NaOH
| |
D2O
CH 2  C  CH 2 D CH 2  C  CH 2 D ⇌ CH 3  CH  CH 2 CH 3 

I2
CH 3CH 2COONa  CHI3
| NaOH
O O OH O
|| ||
H 2O / H 
OH
DCH 2  C  CH 2 D ⇌ D3 C  C  CD3 15. (c) P 
 H 2C H3C
The enol form of acetone on treatment with D2 O undergoes  CH 3
CH 3
Q  
H 2O / H
 H 3 C
enolisation, deutration (addition of D2 O ) and dehydration
(removal of H 2 O ). The repeated enolisation, deutration and OH ⇌ H 3C
dehydration ultimately gives CD3 . COCD 3 (B) . CHO
Ketone (non-reducing) and aldehyde (reducing) can be
9. (b) Both Zn(Hg), HCl and NH 2 NH 2 , OH  can reduce distinguished by Fehling solution.
CH 3
COCH 3 group to CH 2  CH 3 group, but HCl will also 16. (d) C  CHCH 2 CH 2 CH 3 
KMnO 4

bring about dehydration of alcohol to form alkene. Therefore, CH 3
appropriate reagent for the conversion is NH 2 NH 2 , OH  . CH 3
C  O  HOOCCH 2 CH 3
10. (b) 2, 4-hexanedione (a 1, 3-diketone) has the most acidic CH 3
hydrogen. This is because the carbanion left after the removal COC 6 H 5
of H  is resonance stabilised in this case. 17. (bd)  C6 H 5 COCl 
AlCl3

O O
|| || 
CH 3  C  CH 2  C  CH 2 CH 3 
OH
 COOH
2, 4  Hexanedion e H 2O
COC 6 H 5 COC 6 H 5
O O 

Cu
 CO 2
||  || 260 o C
CH 3  C  C H  C  CH 2 CH 3
18. (d) Aldehyde & ketone are colourless & stable compound
O O 19. (c) It undergoes electrophilic substitution at m-position and also
||  ||
gives iodoform test.
CH 3  C  C H  C  CH 2CH 3
20. (a) CH 3  CH 2  C  CH  H 2 O 
But 1  yne
O O
| ||  OH 
 CH 3  C  CH  C  CH 2CH 3  |  keto- enol
CH 3  CH 2  C  CH 2  
O O   tautomerism
|| |  
 CH 3  C  CH  C  CH 2CH 3
O
(a) Aldols (-hydroxy aldehydes or -hydroxyketones) readily
||
11. CH 3  CH 2  C  CH 3
undergo dehydration to form , -unsaturated aldehydes or Butan  2  one
ketones. 21. (b) Due to electron withdrawing nature of NO 2 group, the

O OH O O H2 partial +ve charge on the carbon atom of the  C  O group
H

 in p-nitrobenzaldehyde increases and hence becomes more
-Hydroxyketone O susceptible to nucleophilic attack by CN  ion.
(A) 
 
H ,  H 2O
22. (b) Cannizzaro reaction is an example of hydride ion (H  )
CHO CHO transfer reaction.
12. (b)  o 23. (d) Except Na 2 CO 3 benzophenone react with rest of option.
  
OH / 100 C
Intramolecular 24. (d) The alcohol can be converted to aldehyde group by treating
Cannizzaro reaction
with oxidising agent Pyridinium chloro chromate
CHO CHO 

(C6 H 5 N HCrO3 Cl  ) it is abbreviated as PCC and is called
COO CH 2OH
Collin's reagent. This reagent is used in non aqueous solvent

  
H / H 2O like CH 2Cl 2 It is a very good reagent because it checks the


CHO OOC
COOH CH 2OH
 further oxidation of aldehyde to carboxylic acid while rest
oxidising agent oxidise aldehyde into carboxylic acid. 30. (a) On complete oxidation the obtained compound shows
increament in molecular weight of only 16. It means only one
CH 3 CH 3 oxygen atom is added here. This condition is fulfilled by only
| |
25. (a) C6 H 5  C  O  H 2 NOH   C6 H 5  C  NOH aldehyde which on oxidation gives acid.
H O 2
Acetopheno ne oxime or
methyl phe nyl ketoxime RCHO   RCOOH
[O ]

Hence, original compound must be

2   C6 H 5 NHCOCH 3
H SO
4
Backmann Acetanilide CH 3 CHO  CH 3 COOH
[O ]
rearrangem ent
mol. wt. 44 mol. wt. 60
26. (d) Benzyl alcohol does not have the CH 3 CO  group or
CH 3 CH 2 O  so it will not give the positive iodoform test. Assertion & Reason
27. (c) This is perkin reaction
3. (b) It is true that lower aldehyde and ketones are soluble in water
O O but as the molecular mass increases their solubility decreases.
|| ||
C C On adding Tollen's reagent to a solution of Carbonyl
CH 3 O CH 2  H  CH 3 COO   compound if silver mirror is obtained than it is aldehyde.
O O Therefore Tollen's reagent is used for the identification of
|| || aldehydes and ketones. Here, assertion and reason both are
C C

true but the reason is not the correct explanation of assertion.
CH 3 O C H2
4. (a) Carbonyl compounds having -hydrogen atom condenses to
O produce aldol in presence of alkali.
||
Me C H CH 3  C H  HCH 2 CHO   
dil. NaOH
||
O O O
|| || Acetaldehyde
C C
CH 3 O CH 2  CH  O   
CH 3 COOH
CH 3  CH  CH 2 CHO
|
OH
Aldol
5. (d) Acetylene, on treatment with alkaline KMnO4 is oxidised to
Me O O
|| || produce oxalic acid.
C C
CH 3 O CH 2  CH  OH CH
|||  
4 [O ] COOH
|
CH alk. KMnO 4 COOH
Acetylene Oxalic acid
Therefore, both assertion and reason are false.
Me 6. (b) Acetophenone and benzophenone can be distinguish by
O O iodoform test. Both are carbonyl compounds. Assertion and
 || ||

H
 C C reason both are true but reason is not the correct explanation
 H 2O
CH 3 O CH  CH CH 3 
H O
of assertion.
2

CH 3
7. (c) CH  CHO

CH 3
Me O CH  CH  COOH  CH 3NCOO
 CH 3
28. (b)   
H 2 NCH 3 Isobutanol has -hydrogen atom.
 H 2O
Acetaldehyde, acetone and methyl ketones having CH 3 CO
N  CH 3 group undergo haloform reaction. The halogen atoms of the
 
LiAlH4
methyl group are first replaced by hydrogen atoms. This
29. (c) CH 3  C  C  CH 2  CH 3 

O3 reaction is used as a test of CH 3 CO –group. Due to absence
O
of CH 3 CO –group isobutanal does not give iodoform test.
CH 3  C C  CH 2  CH 3 8. (a) Benzaldehyde is less reactive than ethanol towards
| |
O O nucleophilic attack. The combined effect of –I and +R effect
H 2O of phenyl group is electron donating which increases the
electron density on the carbon atom of the C  O in
benzaldehyde.
CH 3  C  C  CH 2  CH 3  H 2 O 2
|| ||
O O

CH 3 COOH  CH 3 CH 2 COOH
9. (b) Both carbanions (formed in presence of base) and enol form
(formed in presence of an acid) act as nucleophiles and hence
add on the carbonyl group of aldehydes and ketones to give
aldols.
10. (b) The positive inductive effect of two alkyl groups in ketones
makes the carbon atom less positive and makes it less reactive
in comparison to aldehydes.
11. (e) Oximes are more acidic because, there is a delocalisation of 
electrons (i.e., resonance) and it stabilises it and its conjugate
acid. But no such resonance exists in hydroxyl amine base
( NH 2 O  )
12. (e) The bond energy of carbonyl group is 179 Kcal mol and in –1

C  C the bond energy is 145.8 Kcal. The carbonyl group

shows resonance and thus possesses higher bond energy.
CO C  O
13. (b) Both carbon and oxygen are nonmetals and try to complete
their octet. In R  C  O  each has complete octet whereas
in R  C   O, carbon atom has in complete octet.
14. (b) HCHO cannot be prepared by Rosenmund's reduction because
formyl chloride is unstable at room temperature.
15. (e) HCHO reacts with NH 3 to form urotropine
6 HCHO  4 NH 3  (CH 2 )6 N 4  6 H 2 O

16. (c) The anion left after the removal of -hydrogen is stabilized by
resonance effect.
17. (b) Aldehydes which do not contain -hydrogens undergo
Cannizzaro reaction.
CH 3
|
H 3 C  C   CHO
|
CH 3
2, 2 dimethyl propanal (no  hydrogen)

18. (d) Aldehydes having a methyl or methylene group in the -

position or more correctly having atleast one hydrogen atom in
the -position undergo dimerisation in presence of a base at
low temperature to form -hydroxy aldehydes called aldols.
1. Benzophenone can be converted into benzene using O
||
[Tamil Nadu CET 2001]
(c) CH 3  C  CH 3 (d) C 2 H 5 OH
(a) Fused alkali
8. The product of following reaction
(b) Anhydrous AlCl3
 O 2
 is
H / Pt
[Kerala CET 2000]
(c) Sodium amalgam in water
CH OH
(d) Acidified dichromate 3

(a) (b)
2. The reagent(s) which can be used to distinguish acetophenone from CH 3
benzophenone is (are) OH
[CBSE PMT 1990]
(c) H (d)
(a) 2, 4-dinitrophenyl hydrazine
(b) Aqueous solution of NaHSO 3 9. OH
Which of the following aldehydes is most reactive towards
(c) Benedict reagent nucleophilic addition reactions
[Roorkee 1992; RPMT 1997]
(d) I 2 and Na 2 CO 3
(a) HCHO (b) CH 3 CHO
3. When acetaldehyde is heated with Fehling solution, it gives a red
precipitate of [MP PET 1989, 93; (c) C2 H 5 CHO (d) CH 3 COCH 3
IIT 1982; MP PET/PMT 1998; RPMT 2002]
10. Which one of the following gives iodoform test
(a) Cu (b) CuO [AIIMS 1996]
(c) Cu 2 O (d) Cu (OH ) 2 (a) Formaldehyde
4. The general order of reactivity of carbonyl compounds for (b) Ethyl alcohol
nucleophilic addition reactions is [CBSE PMT 1995] (c) Benzyl alcohol
(a) H 2 C  O  RCHO  ArCHO  R 2 C  O  Ar2 C  O (d) Benzaldehyde
11. The active ion in Tollen's reagent is
(b) ArCHO  Ar2 C  O  RCHO  R 2 C  O  H 2 C  O
(a) Cu  (b) Cu (NH 3 )2
(c) Ar2 C  O  R 2 C  O  ArCHO  RCHO  H 2 C  O
(d) H 2 C  O  R 2 C  O  Ar2 C  O  RCHO  ArCHO (c) Ag  (d) Ag(NH 3 )2

5. Which of the following gives an alcohol and salt of carboxylic acid 12. Among the following compounds, which will react with acetone to
when reacted with conc. NaOH give a product containing  C  N 
[MP PMT 1999] [IIT 1998]

(a) CH 3 CHO (a) C 6 H 5 NH 2

(b) C 6 H 5 CHO (b) (CH 3 )3 N

(c) CH 3 COCH 3 (c) C 6 H 5 NHC 6 H 5

(d) C 6 H 5 COCH 3 (d) C 6 H 5 NHNH 2

6. Which of the following compounds would undergo Cannizzaro's 13. Which of the following does not give yellow precipitate with I 2
reaction and NaOH [MP PET 1996]
[CPMT 1989; AFMC 1991; MNR 1995]
(a) C 2 H 5 OH (b) CH 3 CHO
(a) Propionaldehyde
(b) Benzaldehyde (c) CH 3 COCH 3 (d) HCHO

(c) Bromobenzene 14. In this reaction

(d) Acetaldehyde CH 3 CHO  HCN

7. NaOH / H  reacts with [BHU 2003] H  /OH 

CH 3 CH (OH )CN  CH 3 CH (OH )COOH
(a) C 6 H 5 OCH 3 (b) CH 3 OH
an asymmetric centre is generated. The acid obtained would be
(a) 20% D + 80% L-isomer
 (b) D-isomer (a) Friedel-Craft's alkylation
(c) L-isomer (b) Friedel-Craft's acylation
(d) 50% D + 50% L-isomer (c) Cannizzaro reaction
15. Aldehydes are produced in atmosphere by [NCERT 1982]
(d) Claisen condensation
(a) Oxidation of secondary alcohols
18. Which of the following fails to answer the iodoform test.
(b) Reduction of alkenes [CBSE PMT 1989]
(c) Reaction of oxygen atoms with hydrocarbons (a) Pentanone–1
(d) Reaction of oxygen atoms with ozone (b) Pentanone–2
16. Which of the following compounds will give positive test with (c) Propanone–2
Tollen's reagent
(d) Ethanol
[CBSE PMT 1994; Kurukshetra CEE 1998; AFMC 2002]
19. The reagent used for the separation of acetaldehyde from
(a) Acetamide
acetophenone is [AIIMS 2004]
(b) Acetaldehyde
(a) NaHSO 4
(c) Acetic acid
(d) Acetone (b) C 6 H 5 NHNH 2

O O (c) NH 2 OH
|| ||
17. ArH  R  C  Cl 
 Ar  C  R  HCl is an example
Lewis acid
(d) NaOH  I 2
of

(SET -27)

C 6 H 5 COC 6 H 5  KOH   C6 H 6  C6 H 5 COOK

Fusion 2. (d) Acetophenone gives iodoform reaction while benzophenone does
1. (a)
Benzopheno ne Benzene Pot. benzoate
give this.
2  
 3. (c) CH 3 CHO   2Cu  CH 3 COO  Cu 2 O  3 H 2 O
5 OH
C 6 H 5 COOK  KO H  K 2 CO 3  C 6 H 6 Fehling solution Red ppt.
Benzene
4. (a) The size of the alkyle group. Causes hindrance to attacking This reaction is Friedel–Craft’s acylation.
group. As the number and size of the alkyl groups incirease the
18. (a) 1-pentanone is an impossible compound does not have
hindrance to the attack of nucleophile also increases.
Thus the reactivity follows the order O
||
H 2 C  O  RCHO  ArCHO  R 2 C  O  Ar2 C  O . CH 3  C  group.
5. (b) Benzaldehyde does not have the -hydrogen so it will
undergoes cannizzaro’s reaction. 19. (a) NaHSO 3 gives the addition reaction with Aldehyde and only
2C 6 H 5 CHO 
 C 6 H 5 CH 2 OH  C 6 H 5 COONa
NaOH aliphatic ketone. Acetophenone is the aromatic ketone so it
6. (b) C 6 H 5 CHO Aldehydes – Those aldehyde in which   H does not give the addition product with NaHSO 3 aldehyde
atom is absent can participate in Cannizzaro’s reaction. from the addition product with NaHSO 3 which on treatment
7. (c) 2CH 3  CO  CH 3  
dil NaOH with acid or base give again aldehyde.
OH O OH
| || | 
CH 3  C  CH 2  C  CH 3 RCHO  HSO 3 Na  R  C  H   R  CHO

H or

(Diacetone alcohol)
| OH 
| SO 3 Na
CH 3
H C6 H 5 COCH 3  NaHSO 3  No reaction
8. (c)  O   
H 2 / Pt

OH
9. (a) Because alkyl group is absent and they have +ve inductive effect
and increases the electron density on the carbonyl group.
10. (b) The compound having -hydrogen will give iodoform test.
Ethyl alcohol and secondary alcohols also give positive iodoform
test because by the action of halogens in alkaline medium, they
are oxidesed to acetaldehyde and methyl ketones respectively.
CH 3 CH 2 OH  I2
 CH 3 CHO  I2
 CI 3 CHO
NaOH NaOH

CHI 3  HCOONa 

H 2O
NaOH

***

11. (d) During reaction Ag  gets reduced Ag metal and forms silver
mirror.
12. (ad) C 6 H 5 NH 2 and C 6 H 5 NH .NH 2 will give the compounds
containing  C  N -group.

13. (d) HCHO    No reaction

I2 / NaOH

14. (d) CH 3CHO  HCN  CH 3 CHOHCN   

hydrolysis

CH 3 CHOHCOOH
D  L isomer of lacticacid

15. (c) Aldehydes are compounds containing C, H and O . So

hydrocarbons react with atmospheric oxygen to give aldehydes.
16. (b) Tollen’s reagent is ammonical silver nitrate solution. Its
reacting species is Ag  . It oxidises aliphatic as well as
aromatic aldehydes.

R  CHO  Ag    RCOOH  Ag

Redox
reaction

anhyd. AlCl
17. (b) ArH  R  CO  Cl 

3
 Ar  CO  R  HCl