Chapter 20, Problem 20.37P

Interpretation Introduction

(a)

Interpretation:

The product of the reaction between methyl benzoate and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.

Concept introduction:

Carboxylic acid derivatives undergo acyl group substitution reactions when treated with appropriate nucleophiles. The reaction occurs via nucleophilic addition-elimination involving a tetrahedral intermediate. It may also involve proton transfer step(s). The reaction occurs if the possible product is more stable than the reactant. If the two are of comparable stability, the reaction will occur reversibly. The order of increasing stability of acid derivatives is

$\text{acid chloride < acid anhydride < ester }\approx \text{ carboxylic acid < amide < carboxylate anion}$.

Interpretation Introduction

(b)

Interpretation:

The product of the reaction between methyl benzoate and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.

Concept introduction:

Carboxylic acid derivatives undergo acyl group substitution reactions when treated with appropriate nucleophiles. The reaction occurs via nucleophilic addition-elimination involving a tetrahedral intermediate. It may also involve proton transfer step(s). The reaction occurs if the possible product is more stable than the reactant. If the two are of comparable stability, the reaction will occur reversibly. The order of increasing stability of acid derivatives is

$\text{acid chloride < acid anhydride < ester }\approx \text{ carboxylic acid < amide < carboxylate anion}$.

Interpretation Introduction

(c)

Interpretation:

The product of the reaction between methyl benzoate and the given reagent is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.

Concept introduction:

Carboxylic acid derivatives undergo acyl group substitution reactions when treated with appropriate nucleophiles. The reaction occurs via nucleophilic addition-elimination involving a tetrahedral intermediate. It may also involve proton transfer step(s). The reaction occurs if the possible product is more stable than the reactant. If the two are of comparable stability, the reaction will occur reversibly. The order of increasing stability of acid derivatives is

$\text{acid chloride < acid anhydride < ester }\approx \text{ carboxylic acid < amide < carboxylate anion}$.

Interpretation Introduction

(d)

Interpretation:

The product of the reaction between aceetic anhydride and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.

Concept introduction:

Carboxylic acid derivatives undergo acyl group substitution reactions when treated with appropriate nucleophiles. The reaction occurs via nucleophilic addition-elimination involving a tetrahedral intermediate. It may also involve proton transfer step(s). The reaction occurs if the possible product is more stable than the reactant. If the two are of comparable stability, the reaction will occur reversibly. The order of increasing stability of acid derivatives is

$\text{acid chloride < acid anhydride < ester }\approx \text{ carboxylic acid < amide < carboxylate anion}$.

Interpretation Introduction

(e)

Interpretation:

The product of the reaction between methyl benzoate and the given reagent is to be predicted. A complete detailed mechanism is to be drawn if the reaction occurs.

Concept introduction:

Carboxylic acid derivatives undergo acyl group substitution reactions when treated with appropriate nucleophiles. The reaction occurs via nucleophilic addition-elimination involving a tetrahedral intermediate. It may also involve proton transfer step(s). The reaction occurs if the possible product is more stable than the reactant. If the two are of comparable stability, the reaction will occur reversibly. The order of increasing stability of acid derivatives is

$\text{acid chloride < acid anhydride < ester }\approx \text{ carboxylic acid < amide < carboxylate anion}$.