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Chapter 22: Q15. (page 890)

Question: Draw the products of each reaction

a.

b.

Short Answer

Expert verified

Answer

Product formed:

(a)

b.

Step by step solution

01

Step-by-Step Solution  Step 1: Conversion of carboxylic acids to acid chlorides.

In order to convert carboxylic acid to acid chlorides, cannot be used as a nucleophile as it is a weaker base than the leaving group -OH.

Hence, thionyl chloride is used because it converts the OH group of the acid into a better leaving group.

02

Reaction with thionyl chloride.

  • Carboxylic acid reacts with SOCl2and converts the -OH group to -OSOCl (good leaving group) through the loss of a proton.
  • The nucleophile attacks the carbonyl carbon and forms a tetrahedral intermediate; the leaving group (-OSOCl) departs, forming acid chloride.

Reaction (a)

Reaction mechanism for (a)

Reaction (b)

Reaction mechanism for (b)

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