Riddle
1. Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give compound (b).
Compound (b) is reacted with HBr to give (c) which is an isomer of (a). When (a) is reacted
with sodium metal it gives compound (d). C8H18 which is different from the compound formed
when 𝑛-butyl bromide is reacted with sodium. Give the structural formula of (a) and write the
equations for all the reactions.
2. An organic compound (A) with molecular formula C8H8O forms an orange-red precipitate
with 2,4-DNP reagent and gives yellow precipitate on heating with iodine in the presence of
sodium hydroxide. It neither reduces Tollens’ or Fehlings’ reagent, nor does it decolourise
bromine water or Baeyer’s reagent. On drastic oxidation with chromic acid, it gives a
carboxylic acid (B) having molecular formula C7H6O2. Identify the compounds (A) and (B) and
explain the reactions involved.
3. An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative,
reduces Tollens’ reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives
1,2-benzenedicarboxylic acid. Identify the compound.
4. An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute sulphuric
acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid
produced (B). (C) on dehydration gives but-1-ene. Write equations for the reactions involved.
5. An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The
molecular mass of the compound is 86. It does not reduce Tollens’ reagent but forms an
addition compound with sodium hydrogen-sulphate and give positive iodoform test. On
vigorous oxidation it gives ethanoic and Propanoic acid. Write the possible structure of the
compound.
6. (a) An aromatic compound ‘A’ on treatment with aqueous ammonia and heating forms
compound ‘B’ which on heating with Br2 and KOH forms a compound ‘C’ of molecular formula
C6H7N. Write the structures and IUPAC names of compounds A, B and C.
(b) Write tests to distinguish the following pairs of compounds:
i. Aniline and ethylamine
ii. Ethylamine and dimethylamine
7. An amide ‘A’ with molecular formula C7H7On undergoes Hoffmann Bromamide degradation
reaction to give amine ‘B’. B’ on treatment with nitrous acid at 273-278 K form ‘C’ and on
CHEMISTRY BY: MRITYUNJAY SIR (9953761394)
treatment with chloroform and ethanolic potassium hydroxide forms ‘D’. ‘C’ on treatment,
with ethanol gives ‘E’. Identify ‘A’, ‘B’, ‘C’, ‘D’ and ‘E’ and write the sequence of chemical
equations.
8. An organic compound (A) with the molecular formula C9H10O forms 2, 4-DNP derivative,
reduces Fehling solution and undergoes Cannizzaro reaction. On vigorous oxidation, it gives
1, 2-benzene dicarboxylic acid.
i. Identify the compound (A) and write its IUPAC name.
ii. Write the reaction of compound (A) with
1. 2, 4-Dinitrophenyl hydrazine and
2. Fehling solution
iii. Write the equation of compound (A) when it undergoes Cannizzaro reaction.
9. Compound (A) (C6H12O2) on reduction with LiAlH4 gives two compounds (B) and (c). The
compound (B) on oxidation with PCC gives compound (D) which upon treatment with dilute
NaOH and subsequent heating gives compound (E). Compound (E) on catalytic hydrogenation
gives compound (C). The compound (D) is oxidized further to give compound (F) which is
found to be a monobasic acid (Molecular weight = 60). Identify the compounds (A), (B), (C),
(D), (E) and (F).
10. (a) Compound A undergoes Rosenmund reduction to give compound B with molecular
formula C7H6O. Compound B does not give Fehling’s test but reacts with conc. NaOH to give C
and D.
Identify A, B, C and D and write all the reactions involved. Write one chemical test to
distinguish between compound B and propanone.
OR
(b) Compound A with molecular formula (C2H6O) on oxidation by PCC gives compound B,
which on treatment with dilute alkali forms compound C which is a 𝛽-hydroxy aldehyde. B on
oxidation by potassium permanganate forms C. Identify A, B, C and D and write all the
chemical equations involved.
11. An alkyl halide (A) of molecular formula C6H13Cl on treatment with alcoholic KOH gives
two isomeric alkenes (B) and (C) of molecular formula C6H12. Both alkenes on hydrogenation
gives 2,3-dimethylbutane. Write the structures of (A), (B) and (C).
12. An aromatic compound ‘A’ of molecular formula C7H6O2 on treatment with aqueous
ammonia and heating forms compound ‘B’. Compound ‘B’ on heating with Br 2 and aqueous
KOH gives a compound ‘C’ of molecular formula C6H7N. Write the structures of A, B and C.
CHEMISTRY BY: MRITYUNJAY SIR (9953761394)
13. An organic compound ‘A’ with molecular formula C5H8O2 is reduced to n-pentane with
hydrazine followed by heating with NaOH and Glycol. ‘A’ forms a dioxime with hydroxylamine
and gives a positive Iodoform and Tollen’s test. Identify ‘A’ and give its reaction for Iodoform
and Tollen’s test.
14. An organic compound ‘A’ with molecular formula C4H8O2 undergoes acid hydrolysis to
form compounds ‘B’ and ‘C’. Oxidation of ‘C’ with acidified potassium permanganate also
produces ‘B’. Sodium salt of ‘B’ on heating with soda lime gives methane.
1) Identify ‘A’, ‘B’ and ‘C’.
2) Out of ‘B’ and ‘C’, which will have higher boiling point? Give reason.
15. An organic compound (X) having molecular formula C5H10O can show various properties
depending on its structures. Draw each of the structures if it,
1) Gives positive iodoform test.
2) Shows Cannizzaro reaction.
3) Reduces Tollens’ reagent and has a chiral carbon.
16. A primary amine ‘A’ C2H7N reacts with alkyl halide (C2H5I) to give secondary amine ‘B’. ‘B’
reacts with C6H5SO2Cl to give a solid ‘C’ which is insoluble in alkali. Identify ‘A’, ‘B’, ‘C’ and
write all the chemical reactions involved.
17. An alcohol ‘A’, (C3H8O) on oxidation gives compound ‘B’. ‘B’ gives negative Tollens’ test
and reacts with hydrazine to give compound ‘C’. ‘B’ reacts with NaOH and I2 to give yellow
precipitate of ‘D’. Identify ‘A’, ‘B’, ‘C’ and ‘D’.
18. A compound ‘A’ (C2H4O) on oxidation gives ‘B’ (C2H4O). ‘A’ undergoes Iodoform reaction
to give yellow precipitate and reacts with HCN to form the compound ‘C’. ‘C’ on hydrolysis
gives 2-hydroxypropanoic acid. Identify the compounds ‘A’, ‘B’ and ‘C’. Write down equations
for the reactions involved.
19. An organic compound ‘X’ with the molecular formula C5H10O forms 2,4-DNP derivative,
does not reduce Tollens’ reagent but gives positive iodoform test on heating with I2 in the
presence of NaOH. Compound ‘X’ gives ethanoic acid and Propanoic acid on vigorous
oxidation. Write the:
i. Structure of the compound ‘X’.
ii. Structure of the product obtained when compound ‘X’ reacts with 2,4-DNP reagent.
iii. Structures of the products obtained when compound ‘X’ is heated with I2 in the
presence of NaOH.
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20. An organic compound A with molecular formula C7H7NO reacts with Br2 aqueous KOH to
give compound B, which upon reaction with NaNO2 and HCl at 00C gives C.
Compound C on heating with CH3CH2OH gives a hydrocarbon compound B on further reaction
with Br2 water gives white precipitate of compound E.
Identify A, B, C, D, E.
Justify by giving relevant chemical equation.
21. An alcohol A(C4H10O) on oxidation with acidified potassium discharge gives acid B C4H8O2.
Compound A when dehydrated with H2SO4 at 443 K give compound C.
Treatment of C with aqueous H2SO4 gives compound D(C4H10O) which is isomer of A.
Compound D is resistant to oxidation but A can easily be oxidized.
Identify A, B, C, D.
Write reactions involved.
22. An organic aromatic compound A with molecular formula C6H7N is sparingly soluble in
H2O.
A on treatment with dilute HCl gives a H2O soluble compound B. A do react with chloroform in
presence alc. KOH to form an offensive smelling compound C.
A reacts with benzene sulphuryl chloride to form an alkali soluble compound D.
A reacts with NaNO2 and HCl to form a compound E which on reaction with phenol forms an
orange red dye F.
Elucidate the structures of organic compounds from A to F.
23. A ketone A which undergoes haloform reaction gives compound B on reduction. B on
heating with H2SO4 gives C, which forms mono-oxide D.
The compound D on hydrolysis in presence of Zinc dust gives only acetaldehyde. Write
structures and IUPAC names of A, B, C.
Write down reaction involved.
24. You are given 4-organic compounds A, B, C, D. The organic compound A, B, C form an
orange red precipitate with 2,4-DNP reagent.
Compound A, B reduce Tollens reagent while C, D do not.
Both B, C gives yellow precipitate when heated with iodine in presence of NaOH.
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Compound D gives brisk effervescence with sodium bicarbonate solution.
Identify A, B, C, D given the number of carbon atom in three of these carbon compounds is
three while one has 2-carbon atoms. Give explanation for your answer.
25. An organic compound A on C8H6 on treatment with dilute H2SO4 containing mercuric
sulphate gives compound B.
This compound B can also be obtained from a reaction of Benzene with acetyl chloride in
presence of AlCl3. B on treatment with I2 in aqueous KOH gives C and a yellow compound D.
Identify A, B, C, D.
Give chemical reactions involved.
26. An organic compound ‘A’ having the molecular formula C3H8O on treatment with Cu at
573 K, gives ‘B’. ‘B’ does not reduce Fehling’s solution but gives a yellow precipitate of the
compound ‘C’ with I2/NaOH. Deduce the structures of A, B and C.
27. An alkene A with molecular formula C5H10 on ozonolysis gives a mixture of two
compounds, B and C. Compound B gives positive Fehling’s test and also reacts with iodine
and NaOH solution. Compound C does not give Fehling solution test but forms iodoform.
Identify the compounds A, B and C.
28. (A), (B) and (C) are three non-cyclic functional isomers of a carbonyl compound with
molecular formula C4H8O. Isomers (A) and (C) give positive Tollens’ test whereas isomer (B)
does not give Tollens’ test but gives positive iodoform test. Isomers (A) and (B) on reduction
with Zn(Hg)/conc. HCl give the same product (D).
a) Write the structures of (A), (B), (C) and (D).
b) Out of (A), (B) and (C) isomers, which one is least reactive towards addition of HCN?
29. An alkene with molecular formula C5H10 on ozonolysis gives a mixture of two compounds
‘B’ and ‘C’. Compound ‘B’ gives positive Fehling test and also reacts with iodine and NaOH
solution. Compound ‘C’ does not give Fehling solution test but forms iodoform. Identify the
compounds ‘A’. ‘B’ and ‘C’.
30. (a) An organic compound (A) having molecular formula C4H8O gives orange red
precipitate with 2, 4-DNP reagent. It does not reduce Tollens’ reagent but gives yellow
precipitate of iodoform on heating with NaOH and I2. Compound (A) on reduction with NaBH4
gives compound (B) which undergoes dehydration reaction on heating with conc. H 2SO4 to
form compound (C). Compound (C) on ozonolysis gives two molecules of Ethanal. Identify
CHEMISTRY BY: MRITYUNJAY SIR (9953761394)
(A), (B) and (C) and write their structures. Write the reactions of compound (A) with (i)
NaOH/I2 and (ii) NaBH4.
(b) Give reason:
i. Oxidation of Propanal is easier than propanone.
ii. 𝛼-Hydrogen of aldehydes and ketones is acidic in nature.
31. A hydrocarbon (A) with molecular formula C5H10 on ozonolysis gives two products (B) and
(C). Both (B) and (C) give a yellow precipitate when heated with iodine in presence of NaOH
while only (B) gives a silver mirror on reaction with Tollen’s reagent.
a) Identify (A), (B) and (C).
b) Write the reaction of B with Tollen’s reagent.
c) Write the equation for iodoform test for C.
d) Write down the equation for aldol condensation reaction of B and C.
32. An organic compound (A) with molecular formula C2Cl3O2H is obtained when (B) reacts
with red P and Cl2. The organic compound (B) can be obtained on the reaction of methyl
magnesium chloride with dry ice followed by ice hydrolysis.
a) Identify A and B.
b) Write down the reaction for the formation of A from B. What is this reaction called?
c) Give any one method by which organic compound B can be prepared from its
corresponding acid chloride.
d) Which will be the more acidic compound (A) or (B)? Why?
e) Write down the reaction to prepare methane from the compound (B).
33. An aliphatic compound ‘A’ with a molecular formula of C3H6O reacts with phenyl
hydrazine to give compound ‘B’. Reaction of ‘A’ with I2 in alkaline medium on warming gives a
yellow precipitate ‘C’. Identify the compounds A, B and C.
OR
Compound ‘A’ was prepared by oxidation of compound ‘B’ with alkaline KMnO4. Compound ‘A’
on reduction with lithium aluminium hydride gets converted back to compound ‘B’. When
compound ‘A’ is heated with compound ‘B’ in the presence of H 2SO4 it produces fruity smell of
compound ‘C’. To which family the compounds ‘A’, ‘B’ and ‘C’ belong to?
34. An aromatic compound ‘A’ (C8H8O) gives positive 2, 4-DNP test. It gives a yellow
precipitate of compound ‘B’ on treatment with iodine and sodium hydroxide solution.
Compound ‘A’ does not give Tollens’ or Fehling’s test. On drastic oxidation with potassium
permanganate it forms a carboxylic acid ‘C’ (C7H6O2), which is also formed along with the
yellow compound in the above reaction. Identify A, B and C and write all the reactions
involved.
CHEMISTRY BY: MRITYUNJAY SIR (9953761394)
35. A compound ‘X’ with molecular formula C3H9N reacts with C6H5SO2Cl to give a solid,
insoluble in alkali. Identify ‘X’ and give the IUPAC name of the product. Write the reaction
involved.
36. An organic compound (A) with molecular formula C3H7NO on heating with Br2 and KOH
forms a compound (B). Compound (B) on heating with CHCl3 and alcoholic KOH produces a
foul smelling compound (C) and on reacting with C6H5SO2Cl forms a compound (D) which is
soluble in alkali. Write the structures of (A), (B), (C) and (D),
37. A compound ‘A’ on reduction with iron scrap and hydrochloric acid gives compound ‘B’
with molecular formula C6H7N. Compound ‘B’ on reaction with CHCl3 and alcoholic KOH
produces an obnoxious smell of carbylamines due to the formation of ‘C’. Identify ‘A’, ‘B’ and
‘C’ and write the chemical reactions involved.
38. A hydrocarbon ‘A’ (C4H8) on reaction with HCl gives a compound ‘B’ (C4H9Cl), which on
reaction wit 1 mole of NH3 gives compound ‘C’ (C4H11N). On reacting with NaNO2 and HCl
followed by treatment with water, compound ‘C’ yields an optically active alcohol, ‘D’.
Ozonolysis of ‘A’ gives 2 moles of acetaldehyde. Identify compounds ‘A’ to ‘D’. Explain the
reactions involved.
CHEMISTRY BY: MRITYUNJAY SIR (9953761394)