(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.

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Phenylacetone can form two different enols.(a) Show the structures of these enols.(b) Predict which enol will be present in the larger concentration at equilibrium.(c) Propose mechanisms for the formation of the two enols in acid and in base

In the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid diethylamide (LSD): మగవా జి N-H LSD (CH25N;O) Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD? pH =

Show how Gabriel syntheses are used to prepare the following amines.(a) benzylamine

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 17

Expert Solution & Answer

Answer 18

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Want to see the full answer?

Chapter 21 Solutions