(a) Interpretation: To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel. Concept introduction: The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH 2 group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H 2 in the presence of a metal catalyst.

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Answer 1

Question

Chapter 19, Problem 19.14P

Interpretation Introduction

(a)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(b)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(c)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

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Draw a Newman projection for the molecule below from the perspective indicated. Which of the groups (letters A-H) are methyl groups? CH3 H H H A H B ☑ >> H. ABCDEFG I H -H CH3 G D CH F E Numeric 4 points How many gauche interactions exist in the conformation shown in the previous problem? 1

Answer 2

Question

Chapter 19, Problem 19.14P

Interpretation Introduction

(a)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(b)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(c)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

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Answer 3

Question

Chapter 19, Problem 19.14P

Interpretation Introduction

(a)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(b)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(c)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

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Answer 4

Question

Chapter 19, Problem 19.14P

Interpretation Introduction

(a)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(b)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(c)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

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Answer 5

Chapter 19, Problem 19.14P

Interpretation Introduction

(a)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(b)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Interpretation Introduction

(c)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Answer 6

Chapter 19, Problem 19.14P

Interpretation Introduction

(a)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Answer 7

Chapter 19, Problem 19.14P

Interpretation Introduction

(a)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Answer 8

Interpretation Introduction

(b)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Answer 9

Interpretation Introduction

(b)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Answer 10

Interpretation Introduction

(c)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Answer 11

Interpretation Introduction

(c)

Interpretation:

To find out which reduction reaction can be used to carry out the transformation among the Wolff-kishner, Clemmensen, or Raney-nickel.

Concept introduction:

The Wolff-Kishner reduction is used to convert the carbonyl (C=O) group of a ketone or aldehyde into a CH₂ group. The Clemmensen reduction is also used to reduce the C=O group of a ketone or aldehyde. The Raney-nickel reduction is used to reduce the carbonyl group of a ketone or aldehyde to a methylene group. The Wolff-Kishner reduction should be avoided if there is a functional group present that is susceptible to reaction under basic conditions or with strong nucleophiles. The Raney-nickel reduction should be avoided if there is a functional group present that is susceptible to reaction with nucleophilic thiols or with H₂ in the presence of a metal catalyst.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 19 - Prob. 19.1P Ch. 19 - Prob. 19.2P Ch. 19 - Prob. 19.3P Ch. 19 - Prob. 19.4P Ch. 19 - Prob. 19.5P Ch. 19 - Prob. 19.6P Ch. 19 - Prob. 19.7P Ch. 19 - Prob. 19.8P Ch. 19 - Prob. 19.9P Ch. 19 - Prob. 19.10P

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Chapter 19 Solutions