Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 13.10, Problem 22P

(a)

Interpretation Introduction

Interpretation:

A multistep synthesis of the given compounds from the given starting material has to be given.

Concept introduction:

Bromination:

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  1

2-methyl propane undergoes radical bromination which yields the 2-bromo-2-methylpropane.because bromination will occur where the tertiary radical is present. (bromination reactions are more selective reaction).

Formation of epoxide:

The alkene can be converted to epoxide when alkene is treated with MCPBA (m-chloro perbenzoic acid)

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:

A multistep synthesis of the given compounds from the given starting material has to be given.

Concept introduction:

Bromination:

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  3

2-methyl propane undergoes radical bromination which yields the 2-bromo-2-methylpropane.because bromination will occur where the tertiary radical is present. (bromination reactions are more selective reaction).

Oxidation of alcohol:

Alcohols reacts with hypochlorous (oxidizing agent) in the presence of acetic acid which yields the corresponding aldehyde and ketones.

Primary alcohols gives aldehyde, secondary alcohols gives ketone.

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  4

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  5

SN2 reaction:

The alcohols reacts with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms which is bearing alcohol group and yields the corresponding product.

(c)

Interpretation Introduction

Interpretation:

A multistep synthesis of the given compounds from the given starting material has to be given.

Concept introduction:

Bromination:

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  6

2-methyl propane undergoes radical bromination which yields the 2-bromo-2-methylpropane.because bromination will occur where the tertiary radical is present. (bromination reactions are more selective reaction).

Oxidation of alcohol:

Alcohols reacts with hypochlorous (oxidizing agent) in the presence of acetic acid and yields the corresponding aldehyde and ketones.

Primary alcohols gives aldehyde, secondary alcohols gives ketone.

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  7

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  8

SN2 reaction:

The alcohols reacts with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms which is bearing alcohol group and yields the corresponding product.

(d)

Interpretation Introduction

Interpretation:

A multistep synthesis of the given compounds from the given starting material has to be given.

Concept introduction:

Bromination:

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  9

2-methyl propane undergoes radical bromination which yields the 2-bromo-2-methylpropane.because bromination will occur where the tertiary radical is present. (bromination reactions are more selective reaction).

Formation of epoxide:

The alkene can be converted to epoxide when alkene is treated with MCPBA (m-chloro perbenzoic acid)

Organic Chemistry, Chapter 13.10, Problem 22P , additional homework tip  10

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