(a) Interpretation: How to carry out the given transformation is to be shown. Concept introduction: Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an S N 2 reaction. This will yield an alpha-alkylated aldehyde or ketone .

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Answer 1

Question

Chapter 17, Problem 17.46P

Interpretation Introduction

(a)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

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You are asked to use curved arrows to generate the significant resonance structures for the following series of compounds and to label the most significant contributor. Identify the errors that would occur if you do not expand the Lewis structures or double-check the mechanisms. Also provide the correct answers.

Answer 2

Question

Chapter 17, Problem 17.46P

Interpretation Introduction

(a)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

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Answer 3

Question

Chapter 17, Problem 17.46P

Interpretation Introduction

(a)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

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Answer 4

Question

Chapter 17, Problem 17.46P

Interpretation Introduction

(a)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

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Answer 5

Chapter 17, Problem 17.46P

Interpretation Introduction

(a)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Answer 6

Chapter 17, Problem 17.46P

Interpretation Introduction

(a)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Answer 7

Chapter 17, Problem 17.46P

Interpretation Introduction

(a)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How to carry out the given transformation is to be shown.

Concept introduction:

Sodium hydride is a strong base but a poor nucleophile. So it will deprotonate the alpha carbon of the carbonyl compound. This will generate a strong nucleophile as well as a strong base, the enolate ion. This enolate ion attacks the electrophilic carbon in alkyl halides to displace the halide ion in an SN2 reaction. This will yield an alpha-alkylated aldehyde or ketone.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 17 - Prob. 17.1P Ch. 17 - Prob. 17.2P Ch. 17 - Prob. 17.3P Ch. 17 - Prob. 17.4P Ch. 17 - Prob. 17.5P Ch. 17 - Prob. 17.6P Ch. 17 - Prob. 17.7P Ch. 17 - Prob. 17.8P Ch. 17 - Prob. 17.9P Ch. 17 - Prob. 17.10P

Solution Summary: The author explains how the given transformation is carried out using sodium hydride and the desired alkyl halide.

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