Question

Question: Draw the products of each reaction

a.

b.

Short answer

Answer

Product formed:

(a)

b.

Step-by-step solution

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.

Reaction with thionyl chloride.

• Carboxylic acid reacts with ${\mathrm{SOCl}}_2$and 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)