Aldehydes and Ketones - Result Question 42

####43. Base catalysed aldol condensation occurs with

(1984,1M)

(a) propionaldehyde

(b) benzaldehyde

(c) 2-methyl propionaldehyde

(d) 2, 2-dimethyl propionaldehyde

Passage Based Questions

Passage 1

Two aliphatic aldehydes P and Q react in the presence of aqueous K2CO3 to give compound R, which upon treatment with HCN provides compound S. On acidification and heating, S gives the product shown below :

(2010)

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Answer:

Correct Answer: 43. (c)

Solution:

  1. For base catalysed aldol condensation, there must be at least one αH to carbonyl group.

CH3CH2CHO

 Propionaldehyde  (2αH)

2, 2-dimethyl propionaldehyde (no αH)

Passage 1 (For Q. Nos. 44-46)

The given product is an ester, obtained by condensation of a hydroxy acid obtained through hydrolysis of a cyanohydrin :

Acid above is obtained by acid hydrolysis of cyanohydrin S as

S is obtained by nucleophile addition of HCN on R, hence R is

R is obtained by treatment of P and Q with aqueous K2CO3 through aldol condensation reaction as

Passage 2 (For Q. Nos. 47-49) (gives positive iodoform test)

R

S

Passage 3 (For Q. Nos. 50-52)



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