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Chapter 21: Problem 494

Write equations to show the reaction of benzoic anhydride with: (a) water, (b)ethyl alcohol, and (c) aniline.

Short Answer

Expert verified
The reactions of benzoic anhydride with water, ethyl alcohol, and aniline are as follows: a) Hydrolysis with Water: \(C_6H_5C(=O)OC(=O)C_6H_5 + H_2O \rightarrow 2C_6H_5COOH\) b) Nucleophilic Substitution with Ethyl Alcohol: \(C_6H_5C(=O)OC(=O)C_6H_5 + C_2H_5OH \rightarrow C_6H_5COOC_2H_5 + C_6H_5COOH\) c) Nucleophilic Substitution with Aniline: \(C_6H_5C(=O)OC(=O)C_6H_5 + C_6H_5NH_2 \rightarrow C_6H_5C(=O)NH(C_6H_5) + C_6H_5COOH\)

Step by step solution

01

Reaction with Water (Hydrolysis)

When benzoic anhydride reacts with water (H2O), it undergoes hydrolysis to form two molecules of benzoic acid. Chemical equation: \(C_6H_5C(=O)OC(=O)C_6H_5 + H_2O \rightarrow 2C_6H_5COOH\)
02

Reaction with Ethyl Alcohol (Nucleophilic Substitution)

When benzoic anhydride reacts with ethyl alcohol (C2H5OH), it undergoes nucleophilic substitution to form ethyl benzoate and benzoic acid. Chemical equation: \(C_6H_5C(=O)OC(=O)C_6H_5 + C_2H_5OH \rightarrow C_6H_5COOC_2H_5 + C_6H_5COOH\)
03

Reaction with Aniline (Nucleophilic Substitution)

When benzoic anhydride reacts with aniline (C6H5NH2), it undergoes nucleophilic substitution to form N-phenylbenzamide and benzoic acid. Chemical equation: \(C_6H_5C(=O)OC(=O)C_6H_5 + C_6H_5NH_2 \rightarrow C_6H_5C(=O)NH(C_6H_5) + C_6H_5COOH\)

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Most popular questions from this chapter

A chemist added water and acid to an unknown ester of formula \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{2}\) to produce an acid \(\mathrm{X}\) and an alcohol \(\mathrm{Y}\). Oxidation of \(\mathrm{Y}\) with chromic acid produced \(\mathrm{X}\). Determine the structure of the original ester. Write equations for all reactions that occur.

From structural considerations, what can you predict about the acid-base properties of succinimide?

Predict the products of the following reactions: (a) Toluene \(+\) phthalic anhydride \(+\mathrm{AICI}_{3} ;\) followed by \(\mathrm{H}_{2} \mathrm{O}\). (b) The product from (a) \(+\) Cone. \(\mathrm{H}_{2} \mathrm{SO}_{4}+\) heat.

Methyl ethyl ketone can undergo Claisen condensation with a given ester, for example, ethyl benzoate, to yield either of two products, depending upon experimental conditions. What are these two products? How can one tell which product one has obtained?

Hydrolysis of neutral compound (A), \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}_{2}\), gave an acid (B) and an alcohol (C). C reacted with \(\mathrm{PCl}_{3}\) and was then treated with Mg. Addition of \(\mathrm{CO}_{2}\) followed by hydrolysis, yielded an acid identical to (B). Determine the structural formulas of \(\mathrm{A}, \mathrm{B}\) and \(\mathrm{C}\).
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