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Aldehydes and Ketones - Q&A

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7 views3 pages

Aldehydes and Ketones - Q&A

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Shashank Parthiban
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© © All Rights Reserved
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UNIT-8

ALDEHYDES, KETONES AND CARBOXYLIC ACIDS


IMPORTANT QUESTIONS
Q1. Name the following compounds according to IUPAC system of nomenclature:

(i) CH3CH(CH3) CH2CH2CHO


(ii) CH3CH2COCH(C2H5) CH2CH2Cl
(iii) CH3CH=CHCHO
(iv) CH3COCH2COCH3
(v) CH3CH(CH3) CH2C(CH3)2COCH3
(vi) (CH3)3CCH2COOH
(vii) OHCC6H4CHO-p

Ans.

(i) 4-methyl pentanal


(ii) 6-chloro-4-ethylhexan-3-one
(iii) But-2-enal
(iv) Pentane-2,4-dione
(v) 3,3,5-trimethyl hexane-2-one
(vi) 3,3-dimethylbutanoic acid
(vii) Benzene-1,4-dicarbaldehyde

Q2. 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 p-Fluorobenzaldehyde
(iv) Ethanenitrile to ethanal
(v) Allyl alcohol to propenal
(vi) But-2-ene to ethanal

Ans.

(i) C5H5NH+CrO3Cl- (PCC)


(ii) Anhydrous CrO3 or K2Cr2O7 in acidic medium
(iii) CrO3 in the presence of acetic anhydride or 1. CrO2Cl2 2. H2O
(iv) (Di isobutyl) Aluminium hydride (DIBAL-H)
(v) PCC
(vi) O3 /H2O-Zn dust

Q3. Arrange the following compounds in the increasing order of their boiling points:
CH3CH2CH2CHO, CH3CH2CH2CH2OH, H5C2 -O-C2H5 and CH3CH2CH2CH3

Ans. Increasing order of boiling points of the given compounds is as follows:

CH3CH2CH2CH3 < H5C2 -O-C2H5 < CH3CH2CH2CHO < CH3CH2CH2CH2OH

Q4. Although phenoxide ion has more number of resonating structures than carboxylate
ion,carboxylic acid is a stronger acid than phenol. Why?
Ans. The electronic charge in the carboxylate ion is more dispersed in comparison to
phenoxide ion. Carboxylate ion is more stable as compared to phenoxide ion. The release of
H+ ion is easier from carboxylic acid. It behaves as stronger acid than phenol.

Q5. 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.

Ans. Reactions are as follows:

Q6. 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.

Ans. (i) Butanone < Propanone < Propanal < Ethanal


(ii) Acetophenone < p-Tolualdehyde < Benzaldehyde < p-Nitrobenzaldehyde

Q7. 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.
Ans. 2-Ethyl benzaldehyde
Q8. An organic compound (A) (molecular formula C8H16O2) was hydrolyzed 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.

Ans. A = Butyl butanoate, B = Butanoic acid, C = Butanol

Q9. 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)
Ans. (i) Acetaldehyde > Acetone > Methyl tert-butyl ketone > Di-tert-butyl ketone

(ii) (CH3)2CHCOOH < CH3CH2CH2COOH < CH3 CH (Br) CH2 COOH < CH3CH2CH (Br)COOH

(iii) 4-Methoxybenzoic acid < Benzoic acid < 4-Nitrobenzoic acid < 3, 4-Dinitrobenzoic acid

Q10. Give plausible explanation for each of the following:

(i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6- trimethylcyclohexanonedoes not.
(ii) There are two –NH2 groups in semicarbazide. However, only one is involved in theformation of
semicarbazones.
(iii) During the preparation of esters from a carboxylic acid and an alcohol in the presenceof an acid
catalyst, the water or the ester should be removed as soon as it is formed.

Ans. (i) Cyclohexanone forms cyanohydrin in good yield but 2, 2, 6-trimethylcyclohexanone does not
because of presence of three methyl groups at α -position w.r.t carbonyl group which hinder the
Nucleophilic attack of CN- group due steric hindrance. No such steric hindrance inCyclohexanone.

(ii) Semicarbazide has two –NH2 groups but one of these which is directly attached to C=O is
involved in resonance. Electron density on NH2 group decreases hence it does not act as
nucleophile.

(iii) It is a reversible reaction. Therefore, to shift the equilibrium in the forward direction, thewater or
the ester should be removed as fast as it is formed.

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