Aldehydes, Ketones and Carboxylic Acids

Aldehydes, Ketones and Carboxylic Acids

Question

straight a right parenthesis space Write space the space structure space of space straight A space and space straight B space in space the space following space reactions colon
straight i right parenthesis thin space CH subscript 3 COCl space rightwards arrow with straight H subscript 2 space Pd minus space BaSO subscript 4 on top space straight A space rightwards arrow with straight H subscript 2 straight N minus OH on top space straight B

ii right parenthesis thin space CH subscript 3 MgBr space rightwards arrow from 2. straight H subscript 3 straight O to the power of plus to 1. space CO subscript 2 of space straight A space rightwards arrow with PCl subscript 5 on top space straight B
b) 

Distinguish between:
i) C6H5-COCH3 and C6H5-CHO
ii) CH3COOH and HCOOH

c) Arrange the following in the increasing order of their boiling points:
CH3CHO,CH3COOH,CH3CH2OH

Or

a) Write the chemical reaction involved in Wolff Kishner reduction.

b) Arrange the following in the increasing order of their reactivity towards nucleophilic addition reaction:
C6H5COCH3, CH3-CHO, CH3COCH3

c) why carboxylic acid does not give reactions of carbonyl group ?

d) Write the product in the following reaction

CH subscript 3 CH subscript 2 CH equals CH minus CH subscript 2 CN space rightwards arrow from 2. space straight H subscript 2 straight O to 1. space left parenthesis straight i minus Bu right parenthesis subscript 2 divided by AlH of

e) A and B are two functional isomers of compound C3H6O. On heating with NaOH and I2, isomers B forms a yellow precipitate of iodoform whereas isomer A does not form any precipitate. Write the formulae of A and B.

Answer
straight i right parenthesis thin space CH subscript 3 COCl space rightwards arrow with straight H subscript 2 space Pd minus space BaSO subscript 4 on top space CH subscript 3 CHO space rightwards arrow with straight H subscript 2 straight N minus OH on top space CH subscript 3 CH equals straight N minus OH

ii right parenthesis thin space CH subscript 3 MgBr space rightwards arrow from 2. straight H subscript 3 straight O to the power of plus to 1. space CO subscript 2 of space CH subscript 3 COOH space rightwards arrow with PCl subscript 5 on top space CH subscript 3 COCl
b) 

(i)Heat both compounds with NaOH and I2, C6H5COCH3 forms yellow ppt of CHI3 whereas C6H5CHO does not.
(ii)Add ammoniacal solution of silver nitrate (Tollen’s reagent) to both the compounds, HCOOH gives silver mirror but CH3COOH does not.

C) CH3CHO < CH3CH2OH < CH3COOH
Or
a) 
b)C6H5COCH3 < CH3COCH3 < CH3CHO

(c) Because of resonance in the carboxylic group the carbonyl group loses a double bond character.

 d) CH subscript 3 CH subscript 2 CH equals CH minus CH subscript 2 CN space rightwards arrow from 2. space straight H subscript 2 straight O to 1. space left parenthesis straight i minus Bu right parenthesis subscript 2 divided by AlH of space space CH subscript 3 CH subscript 2 CH equals CH minus CH subscript 2 CHO
e) A : CH3CH2CHO B : CH3COCH3

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