The conversion of the given starting material to the indicated nitrile is to be shown. Concept introduction: Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone .

Question

a. Propose a mechanism for the formation of succinic anhydride in the presence of acetic anhydride.b. How does acetic anhydride make it easier to form the anhydride?

Answer 1

Question

Chapter 21.14, Problem 21.38P

(a)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(b)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(c)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

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a. Propose a mechanism for the formation of succinic anhydride in the presence of acetic anhydride.b. How does acetic anhydride make it easier to form the anhydride?

What products would you expect to obtain from the following reactions? a. malonic acid + 2 acetyl chloride b. methyl carbamate + methylaminec. urea + water d. B-ethylglutaric acid + acetyl chloride + ∆

Show how you would use anhydrides to synthesize the following compounds. In eachcase, explain why an anhydride might be preferable to an acid chloride.(a) n-octyl formate (b) n-octyl acetate(c) phthalic acid monoamide (d) succinic acid monomethyl ester

Answer 2

Question

Chapter 21.14, Problem 21.38P

(a)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(b)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(c)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

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Answer 3

Question

Chapter 21.14, Problem 21.38P

(a)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(b)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(c)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

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Answer 4

Question

Chapter 21.14, Problem 21.38P

(a)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(b)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(c)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

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Answer 5

Chapter 21.14, Problem 21.38P

(a)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(b)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

(c)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

Answer 6

Chapter 21.14, Problem 21.38P

(a)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

Answer 7

Chapter 21.14, Problem 21.38P

(a)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The conversion of the given starting material to the indicated nitrile is to be shown.

Concept introduction:

Nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids. They are made from carboxylic acids by conversion to primary amides followed by the removal of water. The reduction of nitrile by lithium aluminium hydride gives a primary amine and the reaction with that of Grignard reagent gives an imine that hydrolyzes to a ketone.

Answer 12

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Answer 23

Ch. 21.2F - Name the following carboxylic acid derivatives,...Ch. 21.4A - Prob. 21.2P Ch. 21.4A - Prob. 21.3P Ch. 21.4A - Prob. 21.4P Ch. 21.5C - Prob. 21.7P Ch. 21.6 - When ethyl 4-hydroxybutyrate is heated in the...Ch. 21.6 - Propose a mechanism for the following ring-opening...Ch. 21.6 - Prob. 21.15P Ch. 21.7B - Prob. 21.16P Ch. 21.7C - Prob. 21.19P

Solution Summary: The author explains that nitriles are considered as acid derivatives because they hydrolyze to carboxylic acids.

Chapter 21 Solutions