(a) Interpretation: The structure of the Weinreb amide on completion of the given reaction is to be predicted. Concept introduction: The Weinreb amides behave as electrophiles. Therefore, they are reactive in the presence of nucleophiles. Weinreb amides are used as a reducing agent and they are selective in nature which converts amides into aldehydes.

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Answer 1

Question

Chapter 21, Problem 21.60AP

Interpretation Introduction

(a)

Interpretation:

The structure of the Weinreb amide on completion of the given reaction is to be predicted.

Concept introduction:

The Weinreb amides behave as electrophiles. Therefore, they are reactive in the presence of nucleophiles. Weinreb amides are used as a reducing agent and they are selective in nature which converts amides into aldehydes.

Interpretation Introduction

(b)

Interpretation:

The structure of the intermediate formed on reaction between Weinreb amide and Grignard reagent is to be drawn. The two reasons for the stability of intermediate to decomposition is to be explained.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism for the break down of tetrahedral intermediate into ketone in the presence of aqueous acid with all products is to be predicted.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(d)

Interpretation:

The products formed when cyclohexanecarbonyl chloride (A) converted into Weinreb amide (B), which further reacts with propylmagnesium bromide (C) followed by protonolysis are to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(e)

Interpretation:

The reason as to why the acid chloride is not reacted with Grignard or oraganolithium reagent instead of using Weinreb amide is to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

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Answer 2

Question

Chapter 21, Problem 21.60AP

Interpretation Introduction

(a)

Interpretation:

The structure of the Weinreb amide on completion of the given reaction is to be predicted.

Concept introduction:

The Weinreb amides behave as electrophiles. Therefore, they are reactive in the presence of nucleophiles. Weinreb amides are used as a reducing agent and they are selective in nature which converts amides into aldehydes.

Interpretation Introduction

(b)

Interpretation:

The structure of the intermediate formed on reaction between Weinreb amide and Grignard reagent is to be drawn. The two reasons for the stability of intermediate to decomposition is to be explained.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism for the break down of tetrahedral intermediate into ketone in the presence of aqueous acid with all products is to be predicted.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(d)

Interpretation:

The products formed when cyclohexanecarbonyl chloride (A) converted into Weinreb amide (B), which further reacts with propylmagnesium bromide (C) followed by protonolysis are to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(e)

Interpretation:

The reason as to why the acid chloride is not reacted with Grignard or oraganolithium reagent instead of using Weinreb amide is to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

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Answer 3

Question

Chapter 21, Problem 21.60AP

Interpretation Introduction

(a)

Interpretation:

The structure of the Weinreb amide on completion of the given reaction is to be predicted.

Concept introduction:

The Weinreb amides behave as electrophiles. Therefore, they are reactive in the presence of nucleophiles. Weinreb amides are used as a reducing agent and they are selective in nature which converts amides into aldehydes.

Interpretation Introduction

(b)

Interpretation:

The structure of the intermediate formed on reaction between Weinreb amide and Grignard reagent is to be drawn. The two reasons for the stability of intermediate to decomposition is to be explained.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism for the break down of tetrahedral intermediate into ketone in the presence of aqueous acid with all products is to be predicted.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(d)

Interpretation:

The products formed when cyclohexanecarbonyl chloride (A) converted into Weinreb amide (B), which further reacts with propylmagnesium bromide (C) followed by protonolysis are to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(e)

Interpretation:

The reason as to why the acid chloride is not reacted with Grignard or oraganolithium reagent instead of using Weinreb amide is to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

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Answer 4

Question

Chapter 21, Problem 21.60AP

Interpretation Introduction

(a)

Interpretation:

The structure of the Weinreb amide on completion of the given reaction is to be predicted.

Concept introduction:

The Weinreb amides behave as electrophiles. Therefore, they are reactive in the presence of nucleophiles. Weinreb amides are used as a reducing agent and they are selective in nature which converts amides into aldehydes.

Interpretation Introduction

(b)

Interpretation:

The structure of the intermediate formed on reaction between Weinreb amide and Grignard reagent is to be drawn. The two reasons for the stability of intermediate to decomposition is to be explained.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism for the break down of tetrahedral intermediate into ketone in the presence of aqueous acid with all products is to be predicted.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(d)

Interpretation:

The products formed when cyclohexanecarbonyl chloride (A) converted into Weinreb amide (B), which further reacts with propylmagnesium bromide (C) followed by protonolysis are to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(e)

Interpretation:

The reason as to why the acid chloride is not reacted with Grignard or oraganolithium reagent instead of using Weinreb amide is to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

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Answer 5

Chapter 21, Problem 21.60AP

Interpretation Introduction

(a)

Interpretation:

The structure of the Weinreb amide on completion of the given reaction is to be predicted.

Concept introduction:

The Weinreb amides behave as electrophiles. Therefore, they are reactive in the presence of nucleophiles. Weinreb amides are used as a reducing agent and they are selective in nature which converts amides into aldehydes.

Interpretation Introduction

(b)

Interpretation:

The structure of the intermediate formed on reaction between Weinreb amide and Grignard reagent is to be drawn. The two reasons for the stability of intermediate to decomposition is to be explained.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism for the break down of tetrahedral intermediate into ketone in the presence of aqueous acid with all products is to be predicted.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(d)

Interpretation:

The products formed when cyclohexanecarbonyl chloride (A) converted into Weinreb amide (B), which further reacts with propylmagnesium bromide (C) followed by protonolysis are to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Interpretation Introduction

(e)

Interpretation:

The reason as to why the acid chloride is not reacted with Grignard or oraganolithium reagent instead of using Weinreb amide is to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Answer 6

Chapter 21, Problem 21.60AP

Interpretation Introduction

(a)

Interpretation:

The structure of the Weinreb amide on completion of the given reaction is to be predicted.

Concept introduction:

The Weinreb amides behave as electrophiles. Therefore, they are reactive in the presence of nucleophiles. Weinreb amides are used as a reducing agent and they are selective in nature which converts amides into aldehydes.

Answer 7

Chapter 21, Problem 21.60AP

Interpretation Introduction

(a)

Interpretation:

The structure of the Weinreb amide on completion of the given reaction is to be predicted.

Concept introduction:

The Weinreb amides behave as electrophiles. Therefore, they are reactive in the presence of nucleophiles. Weinreb amides are used as a reducing agent and they are selective in nature which converts amides into aldehydes.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The structure of the intermediate formed on reaction between Weinreb amide and Grignard reagent is to be drawn. The two reasons for the stability of intermediate to decomposition is to be explained.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The structure of the intermediate formed on reaction between Weinreb amide and Grignard reagent is to be drawn. The two reasons for the stability of intermediate to decomposition is to be explained.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism for the break down of tetrahedral intermediate into ketone in the presence of aqueous acid with all products is to be predicted.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The curved-arrow mechanism for the break down of tetrahedral intermediate into ketone in the presence of aqueous acid with all products is to be predicted.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The products formed when cyclohexanecarbonyl chloride (A) converted into Weinreb amide (B), which further reacts with propylmagnesium bromide (C) followed by protonolysis are to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The products formed when cyclohexanecarbonyl chloride (A) converted into Weinreb amide (B), which further reacts with propylmagnesium bromide (C) followed by protonolysis are to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Answer 14

Interpretation Introduction

(e)

Interpretation:

The reason as to why the acid chloride is not reacted with Grignard or oraganolithium reagent instead of using Weinreb amide is to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Answer 15

Interpretation Introduction

(e)

Interpretation:

The reason as to why the acid chloride is not reacted with Grignard or oraganolithium reagent instead of using Weinreb amide is to be stated.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases. The Grignard reagent is used to increase the chain length of the carbon-carbon bond.

Answer 16

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Answer 17

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Answer 18

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Answer 19

Ch. 21 - Prob. 21.1P Ch. 21 - Prob. 21.2P Ch. 21 - Prob. 21.3P Ch. 21 - Prob. 21.4P Ch. 21 - Prob. 21.5P Ch. 21 - Prob. 21.6P Ch. 21 - Prob. 21.7P Ch. 21 - Prob. 21.8P Ch. 21 - Prob. 21.9P Ch. 21 - Prob. 21.10P

Solution Summary: The author explains the structure of the Weinreb amide on completion of a given reaction.

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Chapter 21 Solutions