Aldehydes , ketones and Carboxylic acids

1. Write the structure of the following

a) 2-methylbutanal
b) 4-chloropentan-2-one
c) p-Methylbenzaldehyde
d) 4-methylpent-3-en-2-one.
e) 1-phenylPropan-1-one
f) 3-oxopentanal
g) α-Methoxypropionaldehyde
h) 3-Hydroxybutanal
i) 2-Hydroxycyclopentane carbaldehyde
j) 4-Oxopentanal
k) Di-sec. butyl ketone
l) 4-Fluoroacetophenone
2. Write the IUPAC name of the following

a. b c
. .
d e f.
. .

g h i.
. .
j. k l
.

m n o

3. Illustrate the following name reaction

a) Wol–Kishner reduction reaction h) Rosenmund’s reduction
b) Cannizzaro’s reaction i) Hell-Volhard-Zelinsky reaction
c) Stephen reaction j) Decarboxylation
d) Etard reaction k) Stephen’s reduction
e) Acetylation l) Gatermann Koch reaction
f) Aldol condensation m) Cross aldol condensation
g) Clemmensen reaction

4. Word problems
a) An organic compound with molecular formula C9H10O forms 2,4-DNP derivative, reduces
Tollen’s reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1,2-
benzenedicarboxylic acid. Identify the compound.
b) 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 I 2 and NaOH. It neither reduces
Tollens’ reagent nor Fehling’s 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.
c) An organic compound A, having the formula, C3H8O, on treatment with copper 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 structure of A, B and C
 d) A and B are two functional isomers of compound C 2H6O. On heating with NaOH and I 2, isomer
B forms yellow precipitate of iodoform whereas isomer A does not form any precipitate.
Write the formulae of A and B.
e) An organic compound (A) which has characteristic odour, on treatment with NaOH forms two
compounds (B) and (C). Compound (B) has the molecular formula C 7H8O which on oxidation
with CrO3 gives back compound (A). Compound (C) is the sodium salt of the acid. Compound
(C) when heated with soda lime yields an aromatic hydrocarbon (D). Deduce the structures of
(A), (B), (C) and (D). Write chemical equations for all reactions taking place.
f) An organic compound with molecular formula C 5H10O does not reduce Tollens’ reagent but
forms an addition compound with sodium hydrogen sulphite and gives a positive iodoform
test. On vigorous oxidation, it gives ethanoic acid and propanoic acid. Identify the compound
and write all chemical equations for the reactions.
g) An organic compound A has the molecular formula C 8H16O2. It gets hydrolysed with dilute
sulphuric acid and gives a carboxylic acid B and an alcohol C. Oxidation of C with chromic acid
also produced B. C on dehydration reaction gives but-1-ene. Write equations for the reactions
involved.
h)
An organic compound contains 69.77% carbon, 11.63% hydrogen and the rest is oxygen. The
molecular mass of the compound is 86. It does not reduce Tollens’ reagent but forms an
addition compound with sodium hydrogen sulphite and gives a positive iodoform test. On
vigorous oxidation it gives enthanoic and propanoic acids. Deduce the possible structure of
the organic compound
i) A ketone A(C4H8O), which undergoes a haloform reaction gives compound B on reduction. B
on heating with sulphuric acid gives a compound C which forms monozonide D. D on
hydrolysis in presence of zinc dust gives only acetaldehyde E. Identify A, B, C, D and E. Write
the reactions involved.
j) An organic compound A(C3H6O) is resistant to oxidation but forms compound B(C 3H8O) on
reduction. B reacts with HBr to form the compound C. C with Mg forms Grignard reagent D
which reacts with A to form a product which on hydrolysis gives E. Identify A and E
5. Conversions

a) Propanone to propane Nitrobromobenzene to 3-

b) Benzoyl chloride to benzaldehyde
c) Ethanal to but-2-enal nitrobenzoic acid (iv) 4-
d) Ethanal to 2-hydroxy propanoic acid Methylacetophenone to
e) Benzoic acid from ethyl benzene.
benzene-1,4-dicarboxylic
f) Propanone to Propene
g) Bromobenzene to 1-phenylethanol acid (v) Cyclohexene to
h) Ethanol to 3-hydroxybutanal hexane-1,6-dioic acid (vi)
i) Benzaldehyde to Benzophenone
Butanal to butanoic acid
j) Write chemical reactions to k) Cyclohexanol to cyclohexan 1-one
affect the following l) Ethanol to acetone.
transformations: Example m) Ethanol to acetone
n) Benzene to acetophenone
12.5 (i) Butan-1-ol to o) Benzoic acid to benzaldehyde
butanoic acid (ii) Benzyl p) Benzaldehyde from toluene
q) Benzaldehyde from Phenol
alcohol to phenylethanoic r) Ethyne to Ethanal
acid (iii) 3-
6. Write the structures of the main products of the following reactions :

a b

c. d
.
e. f.

G
,
7. Write the products formed when ethanal reacts with the following reagents : (i) CH 3MgBr and then H3O+
(ii) Zn-Hg/conc. HCl (iii) C6H5CHO in the presence of dilute NaOH (iv) HCN (vi) H2N OH (vii) CH3CHO in the
presence of dilute NaOH
8. Out of CH3CH2 CO CH2 CH3 and CH3CH2 CH2 CO CH3, which gives iodoform test?
9. Draw the structure of the following derivatives : (i) Propanone oxime (ii)
Semicarbazone of the CH3CHO
10. Give names of the reagents to bring about the following transformations: (i)
Hexan-1-ol to hexanal (ii) Cyclohexanol to cyclohexanone (iii) p-
Fluorotoluene to (iv) Ethanenitrile to ethanal p-fluorobenzaldehyde (v) Allyl
alcohol to propenal (vi) But-2-ene to ethanal
11. Predict the structures of the products formed when benzaldehyde is treated
with (i) conc. NaOH (ii) HNO3/H2SO4 (at 273– 383 K)
12. Arrange the following compounds in increasing order of their boiling points.
CH3 CHO, CH3 CH2OH, CH3OCH3 , CH3 CH2 CH
13. Would you expect benzaldehyde to be more reactive or less reactive in
nucleophilic addition reactions than propanal? Explain your answer
14. Arrange the following compounds in increasing order of their reactivity in
nucleophilic addition reactions. (i) Ethanal, Propanal, Propanone, Butanone.
(ii) Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone.
Hint: Consider steric effect and electronic effect
15. Although phenoxide ion has more number of resonating structures than
carboxylate ion, carboxylic acid is a stronger acid than phenol. Why?
16. Give plausible explanation for each of the following: (i) Cyclohexanone
forms cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not.
(ii) There are two –NH2 groups in semicarbazide. However, only one is
involved in the formation of semicarbazones. (iii) During the preparation of
esters from a carboxylic acid and an alcohol in the presence of an acid
catalyst, the water or the ester should be removed as soon as it is formed.
17. Give simple chemical tests to distinguish between the following pairs of compounds. (i) Propanal and
Propanone (ii) Acetophenone and Benzophenone (iii) Phenol and Benzoic acid (iv) Benzoic acid and Ethyl
benzoate (v) Pentan-2-one and Pentan-3-one (vi) Benzaldehyde and Acetophenone (vii) Ethanal and
Propanal Distinguish between CH3COOH and HCOOH
18. Arrange the following compounds in increasing order of their property as
indicated: (i) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl
ketone (reactivity towards HCN) (ii) CH3CH2CH(Br)COOH,
CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid strength) (iii)
Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-
Methoxybenzoic acid (acid strength)

ACIDS
State reasons for the following : (i) Monochloroethanoic acid has a higher
pKa value than dichloroethanoic acid. (ii) Ethanoic acid is a weaker acid than
benzoic acid.
Give reasons : (i) Electrophilic substitution in benzoic acid takes place at
meta position. (ii) Carboxylic acids do not give the characteristic reactions of
carbonyl group
Butan-1-ol to butanoic acid 242 CBSE Chapterwise-Topicwise Chemistry (ii)
4-Methylacetophenone to benzene-1,4- dicarboxylic acid
Ethylbenzene to benzoic acid (ii) Bromobenzene to benzoic acid
Write the mechanism of esterication of carboxylic acid
Chloroacetic acid is stronger than acetic acid
How are the following conversions carried out : (i) Ethylcyanide to ethanoic
acid (ii) Butan-1-o1 to butanoic acid (iii) Methylbenzene to benzoic acid
Write Chemical equations for the involved reactions.

Which acid of each pair shown here would you expect to be stronger?