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Chapter 22: Q18. (page 892)

Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

Formation of the final product

Step by step solution

01

Step-by-Step SolutionStep 1: The intramolecular esterification

The intramolecular esterification takes place from the and hydroxy carboxylic acids. It occurs in the presence of a strong acid and forms five or six-membered lactones.

During this reaction, the acid protonates the carbonyl group and causes the intramolecular ring closure resulting in the formation of lactones.

02

The stepwise mechanism of the given reaction

  • The first step involves the protonation of the carboxylic acid group followed by the removal of a proton.

First step

  • The second step is the ring closure by the nucleophilic attack of the -OH group on the carbonyl carbon.

Second step

  • The next step is the protonation of the alcohol group.

Third step

  • Finally, a proton is removed by the group:

Formation of the final product

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Most popular questions from this chapter

Question: Without reading ahead in Chapter 22, state whether it should be possible to carry out each of the following nucleophilic substitution reactions.

a.

b.

c.

d.

Question: Explain why trichloroacetic anhydride[Cl3CCO2O] is more reactive than acetic anhydride[CH3CO2O] in nucleophilic acyl substitution reactions.

What amide(s) will form each of the following amines on treatment with LiAlH4?

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