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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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Most popular questions from this chapter

Question: Draw a stepwise mechanism for the formation of A from an alcohol and acid chloride. A was converted in one step to Blattella quinone, the sex pheromone of the female German cockroach Blattella germanica.

Draw a stepwise mechanism for the following reaction.

Which carbon is most electrophilic in Compound Y? Explain your choice.

What aldehyde or ketone is needed to prepare each alcohol by metal hydride reduction?

What reagent is needed to convert (CH3)2CHCH2COCIinto each compound?

a.

b.

c.

d.
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