(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 acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion .

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Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

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111 Carbonyl Chem Choosing reagants for a Wittig reaction What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 3 1 2 2. n-BuLi • Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure. × ©2025 McGraw Hill LLC. All Rights Reserved. Terms of Use

A student proposes the transformation below in one step of an organic synthesis. There may be one or more reactants missing from the left-hand side, but there are no products missing from the right-hand side. There may also be catalysts, small inorganic reagents, and other important reaction conditions missing from the arrow. • Is the student's transformation possible? If not, check the box under the drawing area. . If the student's transformation is possible, then complete the reaction by adding any missing reactants to the left-hand side, and adding required catalysts, inorganic reagents, or other important reaction conditions above and below the arrow. • You do not need to balance the reaction, but be sure every important organic reactant or product is shown. + T X O O лет-ле HO OH HO OH This transformation can't be done in one step.

Determine the structures of the missing organic molecules in the following reaction: X+H₂O H* H+ Y OH OH Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. X S

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

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Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

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Answer 5

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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ 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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 6

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 7

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 8

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 9

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 10

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 11

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 12

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 13

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 14

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 15

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

acid chloride < acid anhydride < ester ≈ carboxylic acid < amide < carboxylate anion.

Answer 16

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Answer 17

Expert Solution & Answer

Answer 18

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Answer 19

Ch. 20 - Prob. 20.1P Ch. 20 - Prob. 20.2P Ch. 20 - Prob. 20.3P Ch. 20 - Prob. 20.4P Ch. 20 - Prob. 20.5P Ch. 20 - Prob. 20.6P Ch. 20 - Prob. 20.7P Ch. 20 - Prob. 20.8P Ch. 20 - Prob. 20.9P Ch. 20 - Prob. 20.10P

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