(a) Interpretation: The product formed by the hydrolysis of given compound is to be determined. Concept introduction: Aldehyde or ketone on reaction with primary amine forms imine. Imine is also known as Schiff base. The nucleophilic attack of primary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an imine.

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Answer 1

Question

Chapter 18.11, Problem 23P

Interpretation Introduction

(a)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with primary amine forms imine. Imine is also known as Schiff base. The nucleophilic attack of primary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an imine.

Interpretation Introduction

(b)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Interpretation Introduction

(c)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

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18. Identify the lactone formed by the following hydroxy carboxylic acid. A. A B. B C. C D. D OH OH & & A) B) C) D)

What carbonyl compound and amine or alcohol are needed to prepare each product?

B. Give the IUPAC name for each compound. a. b. d.

Answer 2

Question

Chapter 18.11, Problem 23P

Interpretation Introduction

(a)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with primary amine forms imine. Imine is also known as Schiff base. The nucleophilic attack of primary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an imine.

Interpretation Introduction

(b)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Interpretation Introduction

(c)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

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Answer 3

Question

Chapter 18.11, Problem 23P

Interpretation Introduction

(a)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with primary amine forms imine. Imine is also known as Schiff base. The nucleophilic attack of primary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an imine.

Interpretation Introduction

(b)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Interpretation Introduction

(c)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

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Answer 4

Question

Chapter 18.11, Problem 23P

Interpretation Introduction

(a)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with primary amine forms imine. Imine is also known as Schiff base. The nucleophilic attack of primary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an imine.

Interpretation Introduction

(b)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Interpretation Introduction

(c)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

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Answer 5

Chapter 18.11, Problem 23P

Interpretation Introduction

(a)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with primary amine forms imine. Imine is also known as Schiff base. The nucleophilic attack of primary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an imine.

Interpretation Introduction

(b)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Interpretation Introduction

(c)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Answer 6

Chapter 18.11, Problem 23P

Interpretation Introduction

(a)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with primary amine forms imine. Imine is also known as Schiff base. The nucleophilic attack of primary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an imine.

Answer 7

Chapter 18.11, Problem 23P

Interpretation Introduction

(a)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with primary amine forms imine. Imine is also known as Schiff base. The nucleophilic attack of primary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an imine.

Answer 8

Interpretation Introduction

(b)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Answer 9

Interpretation Introduction

(b)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Answer 10

Interpretation Introduction

(c)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Answer 11

Interpretation Introduction

(c)

Interpretation: The product formed by the hydrolysis of given compound is to be determined.

Concept introduction: Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Answer 12

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Answer 14

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Answer 15

Ch. 18.1 - Rank the following compounds in order of...Ch. 18.1 - Prob. 2P Ch. 18.2 - Give the IUPAC name for each aldehyde.Ch. 18.2 - Prob. 4P Ch. 18.2 - Give the IUPAC name for each ketone.Ch. 18.5 - Prob. 11P Ch. 18.9 - Problem 21.17 Draw the products of the following...Ch. 18.9 - Problem 21.18 Outline a synthesis of each Wittig...Ch. 18.9 - Problem 21.19 Draw the products (including...Ch. 18.9 - Problem 21.20 What starting materials are needed...

Solution Summary: The author explains that the product formed by the hydrolysis of given compound is benzaldehyde and cyclopentylamine.

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Chapter 18 Solutions