The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH 3 ) 4 C, is a good way to prepare neopentyl chloride, (CH 3 ) 3 CCH 2 Cl is to be explained. Concept introduction: In radical substitution reactions, if the alkane contains different kinds of hydrogens then all of them will be substituted by chlorine and usually a mixture of monochloro substituted products is formed. However if the alkane contains only one type of hydrogen then only one monochloro substituted product will be produced. The reaction will also be fast. To explain: The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH 3 ) 4 C, is a good way to prepare neopentyl chloride, (CH 3 ) 3 CCH 2 Cl.

Question

What is the stepwise mechanism for this reaction?

Answer 1

Question

Chapter 6.SE, Problem 37AP

Interpretation Introduction

Interpretation:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl is to be explained.

Concept introduction:

In radical substitution reactions, if the alkane contains different kinds of hydrogens then all of them will be substituted by chlorine and usually a mixture of monochloro substituted products is formed. However if the alkane contains only one type of hydrogen then only one monochloro substituted product will be produced. The reaction will also be fast.

To explain:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl.

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Answer 2

Question

Chapter 6.SE, Problem 37AP

Interpretation Introduction

Interpretation:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl is to be explained.

Concept introduction:

In radical substitution reactions, if the alkane contains different kinds of hydrogens then all of them will be substituted by chlorine and usually a mixture of monochloro substituted products is formed. However if the alkane contains only one type of hydrogen then only one monochloro substituted product will be produced. The reaction will also be fast.

To explain:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl.

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Answer 3

Question

Chapter 6.SE, Problem 37AP

Interpretation Introduction

Interpretation:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl is to be explained.

Concept introduction:

In radical substitution reactions, if the alkane contains different kinds of hydrogens then all of them will be substituted by chlorine and usually a mixture of monochloro substituted products is formed. However if the alkane contains only one type of hydrogen then only one monochloro substituted product will be produced. The reaction will also be fast.

To explain:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl.

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Answer 4

Question

Chapter 6.SE, Problem 37AP

Interpretation Introduction

Interpretation:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl is to be explained.

Concept introduction:

In radical substitution reactions, if the alkane contains different kinds of hydrogens then all of them will be substituted by chlorine and usually a mixture of monochloro substituted products is formed. However if the alkane contains only one type of hydrogen then only one monochloro substituted product will be produced. The reaction will also be fast.

To explain:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl.

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Answer 5

Chapter 6.SE, Problem 37AP

Interpretation Introduction

Interpretation:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl is to be explained.

Concept introduction:

In radical substitution reactions, if the alkane contains different kinds of hydrogens then all of them will be substituted by chlorine and usually a mixture of monochloro substituted products is formed. However if the alkane contains only one type of hydrogen then only one monochloro substituted product will be produced. The reaction will also be fast.

To explain:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl.

Answer 6

Chapter 6.SE, Problem 37AP

Interpretation Introduction

Interpretation:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl is to be explained.

Concept introduction:

In radical substitution reactions, if the alkane contains different kinds of hydrogens then all of them will be substituted by chlorine and usually a mixture of monochloro substituted products is formed. However if the alkane contains only one type of hydrogen then only one monochloro substituted product will be produced. The reaction will also be fast.

To explain:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl.

Answer 7

Chapter 6.SE, Problem 37AP

Interpretation Introduction

Interpretation:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl is to be explained.

Concept introduction:

In radical substitution reactions, if the alkane contains different kinds of hydrogens then all of them will be substituted by chlorine and usually a mixture of monochloro substituted products is formed. However if the alkane contains only one type of hydrogen then only one monochloro substituted product will be produced. The reaction will also be fast.

To explain:

The observation that radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane, (CH₃)₄C, is a good way to prepare neopentyl chloride, (CH₃)₃CCH₂Cl.

Answer 8

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Answer 19

Ch. 6.1 - Prob. 1P Ch. 6.3 - Prob. 2P Ch. 6.3 - Using curved fishhook arrows, propose a mechanism...Ch. 6.4 - Prob. 4P Ch. 6.4 - An electrostatic potential map of boron...Ch. 6.5 - What product would you expect from reaction of...Ch. 6.5 - Reaction of HBr with 2-methylpropene yields...Ch. 6.6 - Prob. 8P Ch. 6.6 - Predict the products of the following polar...Ch. 6.7 - Which reaction is more energetically favored, one...

Solution Summary: The author explains that radical chlorination of pentane is a good way to prepare neopentyl chloride.

Chapter 6 Solutions