ALDEHYDE AND KETONE-EXERCISE

(1) C2H5CHO
SECTION - A
(2) CH3 – O – CH3
NCERT Based MCQs
O
1. Final product (B) obtained in the following sequence
of reactions is [NCERT Pg. 362] (3) CH 3 – C – CH 3
(i) DIBAL – H (i) NH2NH2
CH2 = CH – CH2 – CN A B O
(ii) H2O (ii) KOH/
(4) Ph – C – H
(1) CH3 – CH2 – CH2 – CH3
(2) CH2 = CH – CH3 5. Product obtained in the following reaction is called

(3) CH2 = CH – CH2 – CH3 R CH2 – OH HCl gas

C= O +
(4) CH3 – CH = CH – CH3 CH2 – OH
R
2. Which of the following pairs can be distinguished
[NCERT Pg. 367]
by Fehling test? [NCERT Pg. 369]
(1) HCHO and CH3 – CHO (1) Acetal (2) Hemiacetal

O (3) Ketal (4) Cyanohydrin

CHO C – CH3 6. Product (C) obtained in the following sequence of

(2) and reaction is [NCERT Pg. 363]

CHO Anhyd. AlCl 3 Cl2(2eq.)/h H 2O

+ CH 3 – Cl A B C
373k
(3)
and CH3CHO
CH 2 – OH
(1)
CHO
O
CH2 – Cl
(4) (2)
and CH3 – C – CH 3

3. Which of the following reactions will produce COOH

Schiff’s base? [NCERT Pg. 368] (3)

(1) C = O + NH 2 – OH CHO
(4)
(2) C = O + CH 3 – NH 2
7. Correct order of reactivity of the following carboxylic
(3) C = O + H 2N – NH 2 acid towards esterification reaction is
[NCERT Pg. 382]
O
(1) HCOOH < CH3COOH < C2H5COOH
(4) C = O + H2N – C – NH 2
(2) CH3COOH < HCOOH < C2H5COOH
4. Which of the following compounds will form yellow
(3) C2H5COOH < HCOOH < CH3COOH
precipitate when treated with alkaline I2 solution?
[NCERT Pg. 370] (4) C2H5COOH < CH3COOH < HCOOH
8. Consider the following reactions [NCERT Pg. 361] 12. Consider the following reaction. [NCERT Pg. 376]

a.
Cu(573 K)
CH3CH2OH   A CH2CH3

KMnO4 - KOH H3O
CH3 – CH(OH) – C2H5 
 B Cu(573 K) A B(major)
b. 

Products A and B respectively are

Major product B is
(1) Aldehyde and ketone
CH2CHO CH2CH2OH
(2) Ketone and aldehyde
(1) (2)
(3) Alkene and ketone
(4) Aldehyde and alkene
9. Number of optically active products formed in HO – CH – CH3 COOH
following reaction is [NCERT Pg. 367]
(3) (4)
(i) OH–
C6H5CHO + HCN 
+

(ii) H
13. When benzaldehyde is treated with a mixture of
(1) 1 nitric acid and sulphuric acid at 273 K then the
major product formed is [NCERT Pg. 373]
(2) 3
OH CHO
(3) 4
NO 2
(4) 2 (1) (2)
NO2
10. Consider the reactions. [NCERT Pg. 361]
CHO CHO
(i) BH 3 /TH F PC C
a. CH3 – CH = CH 2 – A B NO2
(ii) H 2O 2/OH (in CH 2Cl2) (3) (4)

b. NO 2 NO2
14. Most acidic compound among the following is
Product B and D are [NCERT Pg. 381]
(1) Functional isomers (2) Positional isomers COOH
(3) Chain isomers (4) Metamers
(1)
11. Consider the following reactions.[NCERT Pg. 383]

(i) Br /Red P
2 COOH
CH3CH2COOH 
(ii) H O
 A. major product A
2 NO2
is (2)

O
 COOH
(1) CH3 CH2 — C — Br

(2) CH3CH2CH2Br (3)

NO2
Br O
  COOH
(3) CH3 CH — C — OH

O (4)

(4) Br  CH2  CH2  C  OH NO2
15. The reaction given below is called (1) CH 3 – C = O + CH 3 – CHO
[NCERT Pg. 363] CH 3
CH3 CHO (2) CH3 – C = O + CH 3 – COOH
CH3
1. CrO2 Cl2 /CS2
2. H 3O
+ O
(3) CH 3 – C CH – CH3
O O
(1) Stephen reaction CH3
(2) Wolff-Kishner reduction O O
(3) Rosenmund reduction (4) CH 3 – C CH – CH3
O O
(4) Etard reaction CH3
5. The slowest step of Cannizzaro's reaction is

SECTION - B (1) Attack of nucleophile

Objective Type Questions (2) Hydride shift

1. What is the I.U.P.A.C. name of the following (3) Transfer of proton

compound? (4) All of these
O
6. Which of the following will not give bisulphite
C–H addition product?
(1) H – CHO (2) CH3 – CHO
(1) Cyclohexanal
(2) Cycloheptan-1-al O O
(3) Cyclohexylmethanal (3) C2H5 – C – C2H5 (4) CH 3 – CH 2 – C – H

(4) Cyclohexanecarbaldehyde 7. Which compound gives Iodoform reaction?

2. Which of the following is Crotonaldehyde?
O O
(1) CH2 = CH – CHO || ||
(1) CH 3 – C – CH 3 (2) Cl – C – CH 3
(2) CH3 – CH = CH – CHO
OH O
CHO ||
(3) (3) H2N – C – CH3 (4) All of these

(4) CH3CHO
O
3. Which of the following is a gas at room HCl
8. CH3 – C – H + CH3OH gas
temperature?
(1) HCHO OCH3
(2) CH3CH2CHO HCl
A + CH3OH gas
CH3 – CH – OCH3 + H2O
O
(3) CH3 – C – CH 3 A is

(1) Classified as acetal

(4) Both (1) & (2)
4. an intermediate. (2) Classified as ketal
CH3 – C = CH – CH 3 + O 3
CH3 (3) Classified as hemiacetal

The intermediate is (4) Classified as hemiketal

9. Which of the following will not give DNP test? O
conc. NaOH
(1) CH3–CHO (2) CH3–CO–CH3 14. CH3 – CH – C – H major product(s)
CH3
CHO
(3) CH3–O–CH3 (4) What will be the major product(s) product of above
reaction?
10. Benzaldehyde reacts with acetic anhydride in
– +
presence of sodium acetate at 180ºC then the (1) CH3 – CH – COONa
product formed is
CH3
(1) Butanoic acid (2) Cinnamic acid (2) CH3 – CH – CH2 – OH
(3) Crotonic acid (4) Acrylic acid CH3
OH H O
O
11. + KOH electrolysis (3) CH3 – CH – CH – C – C – H
CH3 – C – H + 2[Ag(NH3)2] A B
H CH3
B is
(4) Both (1) & (2)
(1) CH3 – CH3
15. When salicylic acid is reacted with methanol in
presence of concentrated H2SO4, then the drug
O
formed is
(2) CH3 – C – OH
(1) Aspirin (2) Salol
O (3) Oil of wintergreen (4) Dettol
– +
(3) CH3 – C – OK 16. Which of the following will give H– during the
following reaction?
(4) CH4
O O
12. Which of the following doesn't reduce Fehling's
solution? H–C–H+ C–H [Link]

(1) CH3 – CHO (2) H – CHO

O
O
O O C–H
(1) H – C – H (2)
(3) H – C – OH (4) CH3 – C – CH3
CH2 – OH
O (3) HCOOH (4)

13. CH3 – C – H + dil. NaOH A B. O
B is ? C–H
H2SO4 (conc.)
O 17. + HNO3 (conc.) A .
(major)
(1) CH3 – C – ONa
– + A is ?
(2) CH3 – CH2OH CHO CHO
NO2
OH O (1) (2)
(3) CH3 – CH – CH2 – C – H NO2

CHO CHO
O NO2 NO2

(4) CH3 – C = CH – C – H (3) (4)

H NO2 NO2
18. 40% aqueous solution of Methanal is called as 24. Which acid derivative is readily hydrolysed?
(1) Formalin (1) CH3COCl
(2) Salol (2) CH3CONH2
(3) Wood spirit (3) (CH3CO)2O
(4) Aspirin (4) CH3COOC2H5
1 PdCl2 H Cl
19. CH2  CH2  H2O  O2  
 A 
298
B
2 CuCl2
THF CO H 
25.  Mg   A 
2
 B C
B is pleasant smelling liquid. What is B? (1 equivalent)

Br
CH3 C is ?
O
O O
(1) CH3 – C – H (2) COOH Cl
CH3 O CH3
(1) (2)
(3) Metaldehyde (4) Trioxane
COOH COOH
20. Which of the following will not be counted among
long chain fatty acids? COOH Cl
(1) C13H27COOH (2) C7H15COOH (3) (4)
(3) C15H31COOH (4) C17H35COOH
Br
21. In which of the following H-bond is present even in
vapour phase? 26. Which carboxylic acid does not give HVZ reaction?

O (1) Acetic acid

(1) CH3 – CH2 – OH (2) CH3 – C – OH (2) Propanoic acid
(3) 2, 2-dimethyl propanoic acid
O
(4) 2-methyl propanoic acid
(3) CH3 – C – H (4) CH3 – NH2
27. Which of the following is the most stable?
22. Which carboxylic acid has highest pKa value?
–
CH3 O O

(1) HCOOH (2) CH 3 – CH – COOH (1) H – C – O (2)

CH3

(3) CH3CH2COOH (4) CH3 – C – COOH (3) CH3  O (4) CH3 – CH – O

CH3
CH3

28. Which of the following will be decarboxylated most
H NaOH CaO
23. CH3  C  N  H2O  A  B easily ?

(excess)

O
B is
(1) CH 3 – C – OH
O O
(2) CH2 = CH – CH2 – COOH
(1) CH3 – C – NH2 (2) CH3 – C – OH
CH2 – COOH
O (3)
COO H
(3) CH3 – C – ONa (4) CH4 (4) CH3 – CH2 – COOH
29. Ca(OH)2
CH3CH2COOH  B 33. Dry distillation of calcium acetate gives

(1) Acetaldehyde
B is
(2) Ethane
O
(3) Acetic acid
(1) CH3 – CH2 – C – OH
(4) Acetone

 O  34. Pyrolysis of acetone gives CH2=C=O called

 
(2) CH3 – CH2 – C – O 2 Ca (1) Methylene oxide
(2) Methyl carbonmonooxide
O
(3) CH3 – CH2 – C – CH2 – CH3 (3) Ketene
(4) Methanone
(4) CH3 – CH2 – CH2 – OH
O 35. Schiff’s reagent is

C – Cl (1) Magenta solution decolourised with

30. NaOH
+ CH3NH2 sulphurous acid

O (2) Ammoniacal cobalt chloride solution

C–NH–CH3 (3) Ammoniacal manganese sulphate solution
+ HCl
(4) Magenta solution decolourised with chlorine
Above reaction is known as
36. HCHO and CH3–CHO differ from each other in
(1) Carbylamine reaction reaction with
(2) Esterification (1) Schiff’s reagent (2) Fehling solution
(3) Hoffmann Bromamide reaction (3) Ammoniacal AgNO3 (4) I2 and NaOH
(4) Schotten-Baumann reaction 37. Which of the following compound gives a ketone
31. Which of the following will not form alcohol when with Grignard reagent?
reduced with H2 + Pd? (1) Formaldehyde (2) Ethyl alcohol
(1) CH3 – COOH
(3) Methyl iodide (4) Methyl cyanide
O O
38. Hexamethylene tetramine is used as
(2) CH 3 – C – O – C – CH 3
(1) Analgesic (2) Antipyretic
O
(3) CH3 – C – Cl (3) Urinary antiseptic (4) All of these
39. The reaction of chloroform with acetone gives
O
(4) CH 3 – C – NH 2 (1) Mesitylene (2) Ethylidene chloride

O (3) Chloretone (4) Chloral

32. CH3 – CH2 – C – NH2 + HNO 2 A. 40. On heating with HCl, acetone gives

A is ? (1) Mesityl oxide (2) Phorone

(1) CH3 – CH2 – COOH (3) Both (1) & (2) (4) Acetaldehyde
(2) CH3 – COOH 41. The reaction of dimethyl sulphoxide with
acetophenone in the presence of HBr (aq.) gives
(3) CH3 – CH2 – CH2 – NO2
(1) C6H5COCH2OH (2) C6H5COCHO
O
(4) CH3 – C – OCH3 (3) C6H5COCOOH (4) No reaction
42. Consider the following reaction sequences 49. A tribasic acid is
 CaO (1) Oxalic acid (2) Tartaric acid
C4H6O4 C3H6O2 C2H6 .
NaOH
[A] [B] [C] (3) Lactic acid (4) Citric acid
[A] and [B] respectively are O
P2O5
(1) CH3–CH(COOH)2, CH3CH2COOH 50. CH3 – C – OH + NH3 A  B  C

CH2-COOH C is
(2) , CH3–CH2–COOH
CH2-COOH O O
– +
COOCH 3 (1) CH 3 – C – ONH 4 (2) CH 3 – C – NH 2
(3) , CH3–COOCH3
COOCH 3 (3) CH3 – C  N (4) CH3 – CH3
(4) CH3–CH2–COOH, HCHO
43. When ethyl acetate is reacted with excess of
SECTION - C
CH3MgBr followed by hydrolysis to give Previous Years Questions
(1) Acetone 1. When vapours of a secondary alcohol is passed
over heated copper at 573 K, the product formed
(2) Tertiary butyl alcohol
is [NEET-2019 (Odisha)]
(3) Propanol-2
(1) an alkene (2) a carboxylic acid
(4) Acetaldehyde (3) an aldehyde (4) a ketone
44. Treatment of benzoic acid and Cl2 / FeCl3 will give 2. Carboxylic acids have higher boiling points than
(1) p-chlorobenzoic acid aldehydes, ketones and even alcohols of
comparable molecular mass. It is due to their
(2) o-chlorobenzoic acid
[NEET-2018]
(3) 2, 4 dichlorobenzoic acid
(1) Formation of intramolecular H-bonding
(4) m-chlorobenzoic acid (2) Formation of carboxylate ion
45. C2H5CHO and (CH3)2CO can be distinguished by (3) Formation of intermolecular H-bonding
testing with
(4) More extensive association of carboxylic acid
(1) Fehling’s solution (2) Hydroxylamine via van der Waals force of attraction
(3) Sodium bisulphite (4) Phenyl hydrazine 3. Compound A, C8H10O, is found to react with NaOI
(produced by reacting Y with NaOH) and yields a
46. The acid which reduces Tollen’s reagent
yellow precipitate with characteristic smell.
(1) Methanoic acid (2) Ethanoic acid A and Y are respectively [NEET-2018]
(3) Butanoic acid (4) Propanoic acid
47. Product [P] will be (1) H3C CH2 – OH and I2
HI/P
CH3–CH2–COOH 

[P]

(1) Ethane (2) Propane (2) CH2 – CH2 – OH and I2

(3) Butane (4) Hexane
CH3
48. Which of the following compounds will not give
Benzoic acid with KMnO4/ OH ? (3) CH3 OH and I2
(1) C6H5(CH3)2CCH2OH
(2) C6H5CH(CH3)2
CH – CH3 and I2
(3) C6H5CH2OH (4)
OH
(4) C6H5CH(CH3)COOH
4. Of the following, which is the product formed when 7. The correct order of strengths of the carboxylic
cyclohexanone undergoes aldol condensation acids
followed by heating? [NEET-2017] COOH COOH COOH

O O
O
I II III
(1) (2) is [NEET-(Phase-2)-2016]
(1) I > II > III (2) II > III > I
OH O (3) III > II > I (4) II > I > III
8. Reaction of a carbonyl compound with one of the
following reagents involves nucleophilic addition
(3) (4) followed by elimination of water. The reagent is
[Re-AIPMT-2015]
OH O O
(1) Hydrocyanic acid
5. Consider the reactions : (2) Sodium hydrogen sulphite

Cu / [Ag(NH3)2]
+
(3) A Grignard reagent
X 573 K
A Silver mirror
–OH,  observed (4) Hydrazine in presence of feebly acidic solution
(C2H6O)
–OH, 
Y 9. Which one of the following esters gets hydrolysed
O
most easily under alkaline conditions?
NH2 – NH – C – NH2
Z [Re-AIPMT-2015]
OCOCH3
Identify A, X, Y and Z [NEET-2017] (1)
(1) A-Methoxymethane, X-Ethanoic acid, Y-Acetate
ion, Z-hydrazine OCOCH3
(2)
(2) A-Methoxymethane, X-Ethanol, Y-Ethanoic
Cl
acid, Z-Semicarbazide
OCOCH3
(3) A-Ethanal, X-Ethanol, Y-But-2-enal,
(3)
Z-Semicarbazone O2N
(4) A-Ethanol, X-Acetaldehyde, Y-Butanone, OCOCH3
Z-Hydrazone
(4)
6. The correct structure of the product A formed in the H3CO
reaction 10. The oxidation of benzene by V2O5 in the presence
O of air produces [Re-AIPMT-2015]
(1) Benzoic acid (2) Benzaldehyde
H2(gas, 1 atmosphere)
A (3) Benzoic anhydride (4) Maleic anhydride
Pd/carbon, ethanol

is [NEET-(Phase-2)-2016] 11. Treatment of cyclopentanone O with

OH O
methyl lithium gives which of the following species?
(1) (2) [AIPMT-2015]
(1) Cyclopentanonyl biradical
OH OH (2) Cyclopentanonyl anion

(3) (4) (3) Cyclopentanonyl cation

(4) Cyclopentanonyl radical
12. An organic compound "X" having molecular formula 16. The correct order of decreasing acid strength of
C5H10O yields phenyl hydrazone and gives negative trichloroacetic acid (A),trifluoroacetic acid (B),
response to the Iodoform test and Tollen's test. It acetic acid (C) and formic acid (D) is
produces n-pentane on reduction. 'X' could be:
[AIPMT (Prelims)-2012]
[AIPMT-2015] (1) A > B > C > D (2) A > C > B > D
(1) n-amyl alcohol (2) Pentanal (3) B > A > D > C (4) B > D > C > A

(3) 2-pentanone (4) 3-pentanone 17. In the following sequence of reactions

13. Which of the following will not be soluble in KCN H O LiAlH

CH3– Br   A 
3
B  4
 C,
sodium hydrogen carbonate? [AIPMT-2014] ether

the end product (C) is [AIPMT (Prelims)-2012]

(1) 2,4,6 -trinitrophenol
(1) Acetaldehyde (2) Ethyl alcohol
(2) Benzoic acid
(3) Acetone (4) Methane
(3) o-Nitrophenol
18. Predict the products in the given reaction
(4) Benzenesulphonic acid CHO
14. Which one is most reactive towads Nucleophilic 50% KOH
addition reaction? [AIPMT-2014]
Cl
CHO
(1) [AIPMT (Prelims)-2012]
–
CH2OH COO
(1)
COCH3 +
(2)
Cl Cl
CHO
–
CH2OH COO
(2) +
(3)
CH3 OH OH
–
CHO CH2OH CH2COO
(3)
+

(4) Cl Cl
NO2
CH2OH OH
(4) +
15. Reaction by which Benzaldehyde cannot be
prepared
OH OH
[NEET-2013]
19. Which of the following acids does not exhibit
COCl optical isomerism ? [AIPMT (Prelims)-2012]
(1) + H2 in presence of Pd-BaSO4
(1) Lactic acid (2) Tartaric acid

(2) +CO+HCl in presence of anhydrous AlCl3 (3) Maleic acid (4) -amino acids
20. CH3CHO and C6H5CH2CHO can be distinguished
COOH
(3) + Zn/Hg and conc. HCl chemically by [AIPMT (Prelims)-2012]
(1) Tollen's reagent test (2) Fehling solution test
CH3
(4) +CrO2Cl2 in CS2 followed by H3O +
(3) Benedict test (4) Iodoform test
21. Acetone is treated with excess of ethanol in the 25. Which one is a nucleophilic substitution reaction
presence of hydrochloric acid. The product obtained among the following [AIPMT (Prelims)-2011]
is [AIPMT (Prelims)-2012]
(1) CH3CHO + HCN  CH3CH(OH)CN
OH 
(1) (CH3)2C (2) CH3CH = CH2 + H2O H
 CH3– CH – CH3
OC2H5
OH
OC2H5
(2) (CH3)2C (3) RCHO + RMgX  R – CH – R
OC2H5
OH
O
CH3
(3) CH 3CH2CH 2—C—CH 3
(4) CH3– CH2– CH – CH2Br + NH3 
O CH3

(4) CH3CH2CH2—C—CH2CH2CH3 CH3– CH2– CH – CH2NH2

22. Consider the following reaction 26. Clemmensen reduction of a ketone is carried out
in the presence of which of the following?
COCl [AIPMT (Prelims)-2011]
H2
A
Pb – BaSO4 (1) H2 and Pt as catalyst
(2) Glycol with KOH
The product A is [AIPMT (Mains)-2012]
(3) Zn-Hg with HCl
(1) C6H6CHO (2) C6H5OH
(4) LiAlH4
(3) C6H5COCH3 (4) C6H5Cl
27. An organic compound 'A' on treatment with NH3
23. Consider the reaction
gives 'B' which on heating gives 'C' when treated
RCHO + NH2NH2  RCH = N – NH2 with Br 2 in the presence of KOH produces
ethylamine. Compound 'A' is
What sort of reaction is it? [AIPMT (Mains)-2012]
[AIPMT (Mains)-2011]
(1) Electrophilic addition - elimination reaction
(2) Free radical addition - elimination reaction (1) CH3 – CHCOOH (2) CH3CH2COOH
CH3
(3) Electrophilic substitution - elimination reaction
(4) Nucleophilic addition - elimination reaction (3) CH3COOH (4) CH3CH2CH2COOH

24. In a set of reactions m-Bromobenzoic acid gave a 28. Match the compounds given in Column-I with
product D. Identify the product D Column-II and select the suitable option using the
code given below
COOH
Column-I Column-II
SOCl2 NH3 NaOH
B C D a. Benzaldehyde (i) Phenolphthalein
Br2
Br b. Phthalic anhydride (ii) Benzoin
A
condensation
[AIPMT (Prelims)-2011]
c. Phenyl benzoate (iii) Oil of wintergreen
CONH2 SO2NH2
d. Methyl salicylate (iv) Fries rearrangement
(1) (2) [AIPMT (Mains)-2011]
Br Br (1) a(ii), b(iii), c(iv), d(i)
COOH
NH2 (2) a(ii), b(i), c(iv), d(iii)
(3) a(iv), b(i), c(iii), d(ii)
(3) (4)
NH2 Br (4) a(iv), b(ii), c(iii), d(i)
29. The order of reactivity of Phenyl magnesium 33. Which of the following reactions will not result in
bromide (PhMgBr) with the following compounds the formation of carbon-carbon bonds ?

CH3 CH3 Ph [AIPMT (Prelims)-2010]

C = O, C = O and C=O
H H3C Ph (1) Reimer-Tieman reaction

[AIPMT (Mains)-2011] (2) Cannizaro reaction

(1) I > III > II (2) I > II > III (3) Wurtz reaction

(3) III > II > I (4) II > I > III (4) Friedel-Crafts acylation

30. Given are cyclohexanol(I), acetic acid(II), 34. Following compounds are given
2,4,6-trinitrophenol (III) and phenol(IV). In these the a. CH3CH2OH
order of decreasing acidic character will be
b. CH3COCH3
[AIPMT (Prelims)-2010]
c. CH3–CHOH
(1) III > II > IV > I
CH3
(2) II > III > I > IV
(3) II > III > IV > I d. CH3OH

(4) III > IV > II > I Which of the above compound(s), on being warmed
with iodine solution and NaOH, will give iodoform ?
31. In a set of reactions, ethyl benzene yielded a
product D [AIPMT (Mains)-2010]
(1) a, c and d (2) Only b
CH2CH3 KMnO4

KOH
B (3) a, b and c (4) a and b
35. Propionic acid with Br2|P yields a dibromo product.
Br C H OH

2
FeCl
 C 
2 5
 D Its structure would be [AIPMT (Prelims)-2009]
3 H

D would be [AIPMT (Prelims)-2010] Br

(1) H–C–CH2COOH (2) CH2Br–CH2–COBr
CH2–CH–COOC2H5 Br
(1)
Br Br
(3) CH3–C–COOH (4) CH2Br–CHBr–COOH
Br Br
(2) 36. Trichloroacetaldehyde, (CCl 3CHO) reacts with
Br chlorobenzene in presence of sulphuric acid and
CH2COOC2H5 produces [AIPMT (Prelims)-2009]
Cl
COOH
(3)
OCH2CH3 (1) Cl C Cl
H
COOC2H5
OH
(4) (2) Cl C Cl
Br
Cl
32. Among the given compounds, the most susceptible
(3) Cl CH Cl
to nucleophilic attack at the carbonyl group is
CCl3
[AIPMT (Prelims)-2010]
Cl
(1) CH3COOCH3 (2) CH3CONH2 (4) Cl C Cl
(3) CH3COOCOCH3 (4) CH3COCl CH2Cl
37. A strong base can abstract an -hydrogen from 41. The product formed in Aldol condensation is
[AIPMT (Prelims)-2008] [AIPMT (Prelims)-2007]
(1) Alkane (2) Alkene (1) An alpha, beta unsaturated ester
(3) Amine (4) Ketone (2) A beta-hydroxy acid
38. The relative reactivities of acyl compounds towards (3) A beta-hydroxy aldehyde or a beta-hydroxy
nucleophilic substitution are in the order of ketone
[AIPMT (Prelims)-2008] (4) An alpha-hydroxy aldehyde or ketone
(1) Acyl chloride > Ester > Acid anhydride > Amide 42. Reduction of aldehydes and ketones into
(2) Acyl chloride > Acid anhydride > Ester > hydrocarbons using zinc amalgam and conc. HCl
Amide is called [AIPMT (Prelims)-2007]
(3) Ester > Acyl chloride > Amide > Acid (1) Wolf-Kishner Reduction
anhydride
(2) Clemmensen Reduction
(4) Acid anhydride > Amide > Ester > Acyl
(3) Cope Reduction
chloride
(4) Dow Reduction
39. Acetophenone when reacted with a base,
C2H5ONa, yields a stable compound which has the 43. Consider the following compounds
structure ?
[AIPMT (Prelims)-2008] (a) C6H5COCl (b) O2N COCl

CH—CH— (c) H 3C (d) OHC

(1) COCl COCl
OH OH
The correct decreasing order of their reactivity
towards hydrolysis is [AIPMT (Prelims)-2007]
C=CH—C–
(2) (1) (b) > (d) > (a) > (c) (2) (b) > (d) > (c) > (a)
CH3 O
(3) (a) > (b) > (c) > (d) (4) (d) > (b) > (a) > (c)
CH—CH2C 44. Which of the compounds with molecular formula
(3) C5H10 yields acetone on ozonolysis ?
CH3 O
[AIPMT (Prelims)-2007]
CH3 CH3
(1) 2 – Methyl – 1 – butene
C C
(4) (2) 2 – Methyl – 2 – butene
OH OH
(3) 3 – Methyl – 1 – butene
40. Which of the following presents the correct order of (4) Cyclopentane
the acidity in the given compounds ?
45. In a set of reactions propionic acid yielded a
[AIPMT (Prelims)-2007] compound D
(1) FCH2COOH > CH3COOH > BrCH2COOH
SOCl2 NH3
> ClCH2COOH CH3CH2COOH  B  C

(2) BrCH2COOH > ClCH2COOH > FCH2COOH

KOH
  D
> CH3COOH Br2

(3) FCH2COOH > ClCH2COOH > BrCH2COOH The structure of D would be

> CH3COOH [AIPMT (Prelims)-2006]
(4) CH3COOH > BrCH2COOH > ClCH2COOH (1) CH3CH2CH2NH2 (2) CH3CH2CONH2
> FCH2COOH (3) CH3CH2NHCH3 (4) CH3CH2NH2
46. A carbonyl compound reacts with hydrogen cyanide 51. In a set of reactions, acetic acid yielded a product D
to form cyanohydrin which on hydrolysis forms a SOCL Benzene
CH3COOH   A  B
2
racemic mixture of –hydroxy acid. The carbonyl Anhyd. AlCl3
compound is [AIPMT (Prelims)-2006]
HCN HOH
 C  D
(1) Acetaldehyde
The structure of D would be
(2) Acetone
[AIPMT (Prelims)-2005]
(3) Diethylketone
OH COOH
(4) Formaldehyde C COOH (2)
(1) CH2–C–CH3
47. Nucleophilic addition reaction will be most favoured CH3 OH
in [AIPMT (Prelims)-2006]
OH CN
O (3) CH2–C–CH3 (4) C CH3
CN OH
(1) CH3 – CH2 – CH2C – CH3
Questions asked Prior to Medical Ent. Exams. 2005
(2) (CH3)2C = O
52. In the conversion of
(3) CH2CH2CHO
O
(4) CH3CHO X
CH = CH – CH2 – C – CH3
48. Self condensation of two moles of ethyl acetate in
presence of sodium ethoxide yields
OH
[AIPMT (Prelims)-2006]
CH = CH – CH2 – CH
(1) Ethyl butyrate
CH3
(2) Acetoacetic ester

(3) Methyl acetoacetate X is

(4) Ethyl propionate (1) H2/Pt
49. Which of the following is not chiral ? (2) Zn-Hg / HCl

[AIPMT (Prelims)-2006] (3) Li/NH3

(1) 2-Butanol (4) NaBH4

(2) 2, 3-diBromopentane 53. In Tollen’s test, aldehydes

(3) 3-Bromopentane (1) Are oxidised to acids

(4) 2-Hydroxypropanoic acid (2) Are reduced to alcohol

(3) Neither reduced nor oxidised
50. Products of the following reaction
(4) Precipitate Ag+ as AgCl
(1) O3
CH3C  C.CH2CH3 
(2) Hydrolysis
 ....... are 54. Which of the following compound will undergo self
aldol condensation in the presence of cold dilute
[AIPMT (Prelims)-2005] alkali?
(1) CH3CHO + CH3CH2CHO (1) CH  C – CHO
(2) CH3COOH + CH3COCH3 (2) CH2 = CH – CHO
(3) CH3COOH + HOOC.CH2CH3 (3) C6H5CHO
(4) CH3COOH + CO2 (4) CH3CH2CHO
55. Which of the following compounds will give positive 62. First product of the reaction between RCHO and
test with Tollen’s reagent? NH2NH2

(1) Acetic acid (2) Acetone (1) RCH = NNH2 (2) RCH = NH

(3) Acetamide (4) Acetaldehyde (3) RCH2NH2 (4) RCON3

56. The order of reactivity of carbonyl compounds for 63. Which of the following is correct?
nucleophilic addition is (1) On reduction, any aldehyde gives secondary
alcohol
(1) Ar2C = O >R2C = O > ArCHO > RCHO > H2C = O
(2) Reaction of vegetable oil with H2SO4 gives
(2) H2C = O > R2C = O > Ar2C = O > RCHO > ArCHO
glycerine
(3) H2C = O > RCHO > ArCHO > R2C = O > Ar2C = O (3) Ethyl alcohol and iodine with NaOH gives
(4) ArCHO > Ar2C = O > RCHO > R2C = O > H2C = O iodoform

57. The oxidation of toluene with CrO3 in the presence (4) Sucrose on reaction with NaCl gives inverted
of (CH 3 CO) 2 O gives a product A, which on sugar
treatment with aqueous NaOH, produces CN
(1) C6H5COONa (2) 2, 4-diacetyl toluene H3O
64. + CH3MgBr P
(3) C6H5CHO (4) (C6H5CO)2O OCH3
58. When aniline reacts with oil of bitter almonds Product ‘P’ in the above reaction is
(C6H5CHO) condensation takes place and benzal
OH
derivative is formed. This is known as
CH – CH3
(1) Schiff’s base
(2) Benedict’s reagent (1)

(3) Million’s base OCH3

O
(4) Schiff’s reagent
C – CH3
59. Aldol condensation will not take place in
(1) CH3CHO (2) CH3COCH3 (2)

(3) HCHO (4) CH3CH2CHO OCH3

60. The oxidation of toluene to benzaldehyde by CHO

chromyl chloride is called
(3)
(1) Etard reaction
OCH3
(2) Reimer-Tiemann reaction COOH
(3) Wurtz reaction
(4)
(4) Cannizzaro’s reaction
OCH3
61. Polarisation in acrolein can be described as
65. In this reaction CH3CHO + HCN  CH3CH(OH)CN
δ δ H . OH
(1) C H 2  CH  C HO   CH3CH(OH)COOH an asymmetric centre
is generated. The acid obtained would be
δ δ
(2) C H 2  CH  C HO (1) D-isomer
δ δ (2) L-isomer
(3) C H2  CH  CH O
(3) 50% d + 50% l-isomer
δ δ
(4) C H2  CH  CH O (4) 20% d + 80% l-isomer
66. A and B in the following reactions are 70. Lowest pKa is associated with
OH COOH
HCN/ B
R–C–R A R—C (1)
KCN
O R CH2NH2

CN
COOH
(1) A = RRC , B = H3O (2)
OH
CH3
CN
(2) A = RRC , B = H2O/OH COOH
OH (3)
Br
(3) A = RRCH2CN , B = NaOH
COOH
CN
, B = LiAlH4 (4)
(4) A = RRC
OH OCH3

67. Compound A has a molecular formula C2Cl3OH. It

SECTION - D
reduces Fehling’s solution and on oxidation, it
gives a monocarboxylic acid B. If A is obtained by NEET Booster Questions
the action of chlorine on ethyl alcohol, then
1. Which one of the following compounds is least
compound A is
reactive with Nucleophile?
(1) Methyl chloride
O
(2) Monochloroacetic acid
(1) CH3 C Cl
(3) Chloral
O
(4) Chloroform
68. Which one of the following on treatment with 50% (2) C6H5 C NH2
aqueous sodium hydroxide yields the
O
corresponding alcohol and acid?
(1) C6H5CHO (3) CH3 C NH2

(2) CH3CH2CH2CHO O

O (4) C6H5 C Cl
2. In the given reaction
(3) CH3 – C – CH3

(4) C6H5CH2CHO O

69. An ester (a) with molecular formula, C9H10O2 was HOH\H

O [P] , [P] is
treated with excess, of CH3MgBr and the complex,
so formed, was treated with H2SO4 to give an CH3 OH
olefin (b). Ozonolysis of (b) gave a ketone with
molecular formula C 8 H 8 O which shows +ve (1) HOOC – CH2 – CH2 – CH – CH3
iodoform test. The structure of (a) is
(2) CH3 – CH2 – CH2 – CH2 – COOH
(1) H3COCH2COC6H5
(3) HO – CH2 – CH2 – CH2 – COOH
(2) C2H5COOC6H5
(3) C6H5COOC2H5 (4) CH3 – CH2 – CH – CH2 – COOH

(4) p-H3CO  C6H4  COCH3 OH

3. In the given reaction 9. Cyclic polymerization of acetone in presence of
conc. H2SO4 produces
O
H2O/H H2O/H (1) Mesityl oxide
[S] R – C – NH2 R – COOH
(2) Phorone
[S] will be
(3) Metaldehyde
(1) RCN
(4) Mesitylene
(2) RNC
10. Reaction of aldehyde with ammonia derivative
(3) RCHO
perform at pH value
(4) R2CO
(1) 3– 4
4. Which compound shows intramolecular H-bonding
in hydrated form? (2) 7

(1) NH3 (3) 8– 9

(2) C2H5OH (4) 12–14

(3) CCl3CHO 11. Reagent used in Etard’s reaction is

(4) CHCl3 (1) K2Cr2O7

5. Which of the following is disproportionation (2) Cr2O3

reaction? (3) CrO2Cl2
(1) Cannizzaro reaction (4) KMnO4
(2) HVZ reaction 12. CH3CHO + HCN  [A]. Product is
(3) Rosenmund’s reaction (1) Optically active
(4) Stephen’s reduction (2) Cyanohydrin
Cl2 alc. KOH
6. CH3CH2COOH A B. (3) Produce by nucleophilic addition
Red P
What is B? (4) All of these

(1) CH3CH2COCl 13. Which acid derivative have highest boiling point?
(1) Acid chloride
(2) CH2 CHCOOH
(2) Ester
(3) CH3CH2CHO
(3) Acid anhydride
(4) ClCH2CH2COOH
(4) Amide
7. HCOOH reacts with conc. H2SO4 to produce
14. Catalyst used in Wacker’s process is
(1) CO
(1) PdCl2
(2) CO2
(2) PbCl2
(3) NO
(3) Zn/HCl
(4) SO2
(4) SnCl2
8. When acetamide reacts with Br2 and caustic soda,
then we get 15. Cannizzaro’s reaction may be of

(1) Methyl amine (1) Second order

(2) Ethyl amine (2) Third order

(3) Ethene (3) Fourth order

(4) Acetic acid (4) Both (2) & (3)

 O 22. Lactic acid on oxidation by alkaline potassium
C6H5COOOH permanganate gives
16. CH3 C CH3 (A) . Product is
(1) Tartaric acid
(1) Carboxylic acid
(2) Pyruvic acid
(2) Alcohol
(3) Cinnamic acid
(3) Ester
(4) Ether (4) Propionic acid

17. Calcium acetate on heating gives Ozonolysis

23. CH2 C—CH3 (A) + HCHO
(1) Acetic anhydride
CH3 PCl5
(2) Acetone
aq. KOH
(3) Acetaldehyde (C) (B)

(4) Methane The product (C) is

18. Formic acid and acetic acid can be distinguished
(1) CH3CH2CH2OH
by
(1) Phenyl hydrazine (2) CH3—CH2—CH—Cl
(2) NaHCO3 Cl
(3) Tollen’s reagent (3) CH3—C—CH3
(4) All of these O
19. Which one of the following will yield a hydrocarbon
when treated with CH3MgBr? Cl
(1) C6H6 (4) CH3 C CH3

O O Cl

(2) C6H5 C CH2 C C6H5 24. Which of the following is a correct order of
acidity?
(3) C6H5 CHO
(4) C6H5COCl (1) CF3COOH < CCl3COOH < CH3COOH

20. The relative reactivities of acyl compounds towards (2) HCOOH > CCl3COOH > CF3COOH
nucleophilic substitution are in the order of
(3) HCOOH > CH3COOH > CH3—CHCOOH
(1) Acyl chloride > Ester > Acid anhydride > Amide
CH3
(2) Acyl chloride > Acid anhydride > Ester > Amide
(3) Ester > Acyl chloride > Amide > Acid anhydride (4) HCOOH > COOH > CCl3COOH
(4) Acid anhydride > Amide > Ester > Acyl chloride COOH
21. In the given reaction
MgBr
(i) conc. NaOH dry
C6H5COCHO [X], [X] is ether H2O
25. HCN + A B , B is
(ii) H
(1) Cyclopropanol
(1) C6H5COOH
(2) Cyclopropanal
(2) C6H5COCH2OH
(3) C6H5CH(OH)COOH (3) Cyclopropanecarbaldehyde

(4) C6H5CH2OH (4) Cyclopropanenitrile

 30. In the reaction
O3/Zn
26. H2O Product. The product is CHO

Conc. KOH
(1) O = CH—CH2—C—(CH2)4—CHO + HCHO Product
||
O
If one equivalent of each is taken, the major
product will be
(2)
CHO
O O O
C CH2 OH
O
(1)
(3) O + HCOOH
CHO
CHO
O O
C CHO CH2OH
(4)
(2)
+
CHO CHO
27. Clemmensen reduction of a ketone is carried out in OH
the presence of which of the following?
CH2
(1) H2 and Pt as catalyst
(3)
(2) Glycol with KOH + HCOOH

(3) Zn-Hg with HCl

COOH
(4) LiAlH4
CH CHO
28. In the following sequence of reactions
(4)

KCN H3 O
LiAlH4
CH3  Br  A  B 
ether
 C,

the end product (C) is

LiAlH4
(1) Acetaldehyde 31. CH = CH – CHO Product .
(2) Ethyl alcohol
(3) Acetone Product of the reaction is
(4) Methane
CH2 – CH2 – CHO
O (1)

SeO2 HIO4 CaO


A 
B 
C CH2 – CH2 – CHO
29. (2)
H2SO5

D
C and D are respectively
CH2 – CH2CH2OH
(1) Adipic acid, -lactone (3)

(2) Cyclobutane, -lactone

(3) Cyclobutanone, -lactone CH = CH – CH2OH
(4)
(4) Adipic acid, -lactone
32. The number of total final products formed in given 37. Which of the following statement is incorrect about
reaction the reaction of ammonia derivatives with carbonyl
OH
– compounds?
CH 3 CHO 
(1) pH of solution is maintained between 3 to 4
(1) 1
(2) Addition of ammonia derivatives occurs followed
(2) 2
by elimination of H2O
(3) 3
(3) At very low pH (less than 3) ammonia derivatives
(4) 4 are protonated and do not act as nucleophile

33. Iodoform reaction is given by (4) At very high pH reaction becomes explosive

O 38. An organic compound does not reacts with Tollen’s

CH = CH – C – CH3 reagent but undergoes Baeyer Villiger oxidation. The
(1)
compound is

O (1) CH  C–CH2COCH3
CHO
(2) C
O
(2)
(3) CH3 – CH2 – CHO
(4) All of these (3) CH3CHO

34. Aromatic aldehydes undergoes condensation on (4) CH 3 – C – CH 3

heating with an ethanolic solution of KCN. This O
reaction is called as
39. Following compounds are given
(1) Perkin reaction
a. CH3CH2OH
(2) Benzoin condensation
b. CH3COCH3
(3) Claisen condensation
c. CH3 CHOH
(4) Cannizzaro’s reaction
CH3
35. Which of the following carbonyl compound can give
Cannizzaro reaction? d. CH3OH
(1) CCl3CHO Which of the above compound(s), on being warmed
(2) (CH3)3CCHO with iodine solution and NaOH, will give iodoform?

(3) CH3CH2CHO (1) a, c & d

(4) Both (1) & (2) (2) Only b

36. The reactivity of carbonyl compounds towards (3) a, b & c

nucleophilic addition reaction gets affected by
(4) a & b only
(1) Magnitude of positive charge on carbonyl carbon
40. A strong base can abstract an -hydrogen from
atom
(1) Alkane
(2) Steric hindrance

(3) Presence of electron withdrawing groups (2) Alkene

surrounding carbonyl group (3) Ether
(4) All of these (4) Ketone
41. Iodoform test is not given by 45. Which of the following compound gives benzoic acid
on hydrolysis?
(1) Ethanal
(1) Chlorobenzene
(2) Ethanol

(3) 2-pentanone (2) Benzoyl chloride

(4) 3-pentanone (3) Chlorophenol

42. Which of the following reactions will not result in the (4) Chlorotoluene
formation of carbon-carbon bonds?
46. In a set of reactions, ethyl benzene yielded a
(1) Friedel-Craft’s acylation product D.
(2) Reimer-Tiemann reaction
KMnO4 Br2 C2H5OH
(3) Cannizzaro reaction CH2CH3 B C + D
KOH FeCl3 H

(4) Wurtz reaction

43. In a set of reactions acetic acid yielded a product D. ‘D’ would be

SOCl benzene HCN
CH 3 COOH  
2
 A   B 
anhy. AlCl3
COOC2H5
HOH
C   D
The structure of D would be (1)
Br
COOH
C – CH3
(1) CH2–CH–COOC2H5
OH (2)
Br
CN
C–CH3 Br
(2)
OH
(3)
OH Br
CH2–C–CH3 CH2COOC2H5
(3)
CN
COOH
OH
(CH2)2–C–CH3 (4)
(4)
CN OCH2CH3

44. An organic compound 'A' on treatment with NH3 gives 47. What is Z in following sequence of reactions?
'B' which on heating gives 'C' when treated with Br2
in presence of KOH produces ethylamine. Compound Zn CH Cl
alkaline
Phenol 
 X  
3
 Y   Z
'A' is dust anhydrous AlCl3 KMnO 4

(1) CH3 — CHCOOH

(1) Benzene
CH3
(2) Toluene
(2) CH3CH2COOH
(3) Benzaldehyde
(3) CH3COOH

(4) CH3CH2CH2COOH (4) Benzoic acid

48. Which of the following is the correct sequence of O
decreasing reactivity towards hydroxide ion promoted 18
(3) R – C – O – CH3
hydrolysis among the following compounds?

O H (4) R – C – O – R
|| | 16

CH3–C–N O

(I) 52. The correct order of decreasing acid strength of

trichloroacetic acid (A), trifluoroacetic acid (B), acetic
O H NO2
|| | acid (C) and formic acid (D) is
CH3–C–N
(1) A > B > C > D
(II)
(2) A > C > B > D
O H
|| | (3) B > A > D > C
CH3–C–N NO2
(4) B > D > C > A
(III) 53. Which one of the following products is formed when
O H adipic acid is heated?
|| |
CH3–C–N CH2CH2CO
(1) O
(IV) CH2CH2CO
(1) I > II > III > IV (2) II > I > IV > III
CH2CH2COOH
(3) III > II > IV > I (4) I > III > II > IV (2)
+
CH2CH2COOH
P2 O 5 H /H2 O
49. CH3CH2COONH4 X Y.
 CH2 CH2
Y and X respectively are (3) O
CH2 CH2
(1) CH3CH2COOH, CH3CH2CN
(2) CH3CH2CN, CH2CH2COOH CH2—C H2
(4) C=O
(3) CH3CH2CH2COOH, CH3CH2CH3 CH2—CH2

(4) CH3CH3, CH3CH2COOCH3 54. Aspirin is an acetylation product of

50. Acetic acid exist in dimer state in benzene due to
(1) m-Hydroxybenzoic acid
(1) Condensation reaction
(2) o-Dihydroxybenzene
(2) Hydrogen bonding
(3) o-Hydroxybenzoic acid
(3) Presence of carbonyl group
(4) p-Dihydroxybenzene
(4) Strong polar nature
O 55. Which one of the following compounds will react with
16 18 dil. H2SO4
51. CH3 – C – O – H + R – O – H Major product. NaHCO3 solution to give sodium salt and carbon

dioxide?
Product of the reaction is
(1) Acetic acid
O
18
(1) CH3 – C – O – R (2) n-hexanol

(3) Phenol
O
16
(2) CH3 – C – O – R (4) Both (2) & (3)
56. Ethyl benzoate can be prepared from benzoic acid (1) Phosphorus pentachloride
by using (2) Hypochlorous acid

(1) Ethyl alcohol (3) Chlorine

(4) Hydrochloric acid
(2) Ethyl alcohol and dry HCl
59. Propionic acid with Br2 / P yields a dibromo product.
(3) Ethyl chloride Its structure would be
(4) Sodium ethoxide Br
(1) CH3 C COOH
57. In a set of the given reactions, acetic acid yielded a
Br
product C
(2) CH2Br – CHBr – COOH
C6 H6 (i) C2H5MgBr Br
CH3COOH + PCl5  A B (ii) ether H3O+
C
Anh. AlCl3
(3) H C CH2COOH

Product C would be Br
(4) CH2Br – CH2 – COBr
(1) CH3CH(OH)C2H5
Br2 / P excess of NH
60. CH3 CH2 COOH   A    
3
 Y.
(2) CH3COC6H5
The product Y is
(3) CH3CH(OH)C6H5
(1) Lactic acid
C2H5
(2) n-propyl amine
(4) CH3–C(OH)C6H5
(3) Ethylamine
58. The OH group of an alcohol or carboxylic acid can
be replaced by –Cl using (4) Alanine