Question

Arrow pushing mechanism for deet syynthesis from benzoic acid

Answer 1

Answer:

Olivia Miller, Chem 213

Synthetic #2 FFR

Exploring the Usefulness of Carboxylic Acid Derivatives in Nucleophilic Acyl Substitution

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Introduction

Carboxylic acid derivatives are the most widely occurring of all molecules, both in laboratory

chemistry and in biological pathways. Specifically, acid derivatives are compounds in which the

hydroxyl group of the carboxylic acid has been replaced by another acyl substituent that can act as a

leaving group in nucleophilic acyl substitutions. These compounds can be acid halides, acid anhydrides,

esters, thioesters, and amides. Some examples of carboxylic acid derivatives can be seen below in Figure

1.

Figure 1. Examples of carboxylic acid derivatives.

These compounds are extremely valuable in organic chemistry synthesis as result of their primary

nucleophilic acyl substitution reactions. When a nucleophile adds to a carboxylic acid derivative, the

initially formed tetrahedral intermediate eliminates one of the two substituents originally bonded to the