The synthesis reaction of an amidine from benzonitrile by using more than one synthetic step is to be shown. Concept introduction: Benzonitrile is reduced to benzylamine when treated with lithium aluminum hydride. The nucleophilic hydrogen from the hydride adds to the electrophilic carbon in the cyanide group and forms a secondary amine . Rapid reduction by nucleophilic hydrogen from the hydride adds to the carbon. The Π electron from the C=N move to the cationic nitrogen, creating the amine product. In the next step, the amine acts as a nucleophile and attacks the C ≡ N triple bond, followed by the protonation using alcohol. The ethanol is a source of proton in the proton transfer reaction.

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Answer 1

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Chapter 18, Problem 18.53P

Interpretation Introduction

Interpretation:

The synthesis reaction of an amidine from benzonitrile by using more than one synthetic step is to be shown.

Concept introduction:

Benzonitrile is reduced to benzylamine when treated with lithium aluminum hydride. The nucleophilic hydrogen from the hydride adds to the electrophilic carbon in the cyanide group and forms a secondary amine. Rapid reduction by nucleophilic hydrogen from the hydride adds to the carbon. The Π electron from the C=N move to the cationic nitrogen, creating the amine product. In the next step, the amine acts as a nucleophile and attacks the C≡N triple bond, followed by the protonation using alcohol. The ethanol is a source of proton in the proton transfer reaction.

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please draw the complete, detailed mechanism and the product of this reaction.

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a) Draw the mechanism for the reaction of a secondary amine with an acid chloride to make an amide.b) Explain what conditions (acid/basic/neutral; excess of one reagent, etc) are required to carry out this reaction in high yield, and why.

Answer 2

Question

Chapter 18, Problem 18.53P

Interpretation Introduction

Interpretation:

The synthesis reaction of an amidine from benzonitrile by using more than one synthetic step is to be shown.

Concept introduction:

Benzonitrile is reduced to benzylamine when treated with lithium aluminum hydride. The nucleophilic hydrogen from the hydride adds to the electrophilic carbon in the cyanide group and forms a secondary amine. Rapid reduction by nucleophilic hydrogen from the hydride adds to the carbon. The Π electron from the C=N move to the cationic nitrogen, creating the amine product. In the next step, the amine acts as a nucleophile and attacks the C≡N triple bond, followed by the protonation using alcohol. The ethanol is a source of proton in the proton transfer reaction.

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Answer 3

Question

Chapter 18, Problem 18.53P

Interpretation Introduction

Interpretation:

The synthesis reaction of an amidine from benzonitrile by using more than one synthetic step is to be shown.

Concept introduction:

Benzonitrile is reduced to benzylamine when treated with lithium aluminum hydride. The nucleophilic hydrogen from the hydride adds to the electrophilic carbon in the cyanide group and forms a secondary amine. Rapid reduction by nucleophilic hydrogen from the hydride adds to the carbon. The Π electron from the C=N move to the cationic nitrogen, creating the amine product. In the next step, the amine acts as a nucleophile and attacks the C≡N triple bond, followed by the protonation using alcohol. The ethanol is a source of proton in the proton transfer reaction.

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Answer 4

Question

Chapter 18, Problem 18.53P

Interpretation Introduction

Interpretation:

The synthesis reaction of an amidine from benzonitrile by using more than one synthetic step is to be shown.

Concept introduction:

Benzonitrile is reduced to benzylamine when treated with lithium aluminum hydride. The nucleophilic hydrogen from the hydride adds to the electrophilic carbon in the cyanide group and forms a secondary amine. Rapid reduction by nucleophilic hydrogen from the hydride adds to the carbon. The Π electron from the C=N move to the cationic nitrogen, creating the amine product. In the next step, the amine acts as a nucleophile and attacks the C≡N triple bond, followed by the protonation using alcohol. The ethanol is a source of proton in the proton transfer reaction.

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Answer 5

Chapter 18, Problem 18.53P

Interpretation Introduction

Interpretation:

The synthesis reaction of an amidine from benzonitrile by using more than one synthetic step is to be shown.

Concept introduction:

Benzonitrile is reduced to benzylamine when treated with lithium aluminum hydride. The nucleophilic hydrogen from the hydride adds to the electrophilic carbon in the cyanide group and forms a secondary amine. Rapid reduction by nucleophilic hydrogen from the hydride adds to the carbon. The Π electron from the C=N move to the cationic nitrogen, creating the amine product. In the next step, the amine acts as a nucleophile and attacks the C≡N triple bond, followed by the protonation using alcohol. The ethanol is a source of proton in the proton transfer reaction.

Answer 6

Chapter 18, Problem 18.53P

Interpretation Introduction

Interpretation:

The synthesis reaction of an amidine from benzonitrile by using more than one synthetic step is to be shown.

Concept introduction:

Benzonitrile is reduced to benzylamine when treated with lithium aluminum hydride. The nucleophilic hydrogen from the hydride adds to the electrophilic carbon in the cyanide group and forms a secondary amine. Rapid reduction by nucleophilic hydrogen from the hydride adds to the carbon. The Π electron from the C=N move to the cationic nitrogen, creating the amine product. In the next step, the amine acts as a nucleophile and attacks the C≡N triple bond, followed by the protonation using alcohol. The ethanol is a source of proton in the proton transfer reaction.

Answer 7

Chapter 18, Problem 18.53P

Interpretation Introduction

Interpretation:

The synthesis reaction of an amidine from benzonitrile by using more than one synthetic step is to be shown.

Concept introduction:

Benzonitrile is reduced to benzylamine when treated with lithium aluminum hydride. The nucleophilic hydrogen from the hydride adds to the electrophilic carbon in the cyanide group and forms a secondary amine. Rapid reduction by nucleophilic hydrogen from the hydride adds to the carbon. The Π electron from the C=N move to the cationic nitrogen, creating the amine product. In the next step, the amine acts as a nucleophile and attacks the C≡N triple bond, followed by the protonation using alcohol. The ethanol is a source of proton in the proton transfer reaction.

Answer 8

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Answer 10

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Answer 11

Ch. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

Solution Summary: The author describes the synthesis reaction of an amidine from benzonitrile by using more than one synthetic step.

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