Pearson eText Organic Chemistry -- Instant Access (Pearson+)
Pearson eText Organic Chemistry -- Instant Access (Pearson+)
8th Edition
ISBN: 9780135213711
Author: Paula Bruice
Publisher: PEARSON+
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Chapter 12.10, Problem 23P

(a)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Bromination:

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , 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)

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , 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:

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , 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.

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , additional homework tip  4

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , 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:

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , 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.

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , additional homework tip  7

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , 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:

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , 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)

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 12.10, Problem 23P , additional homework tip  10

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Indicate how the following compound can be synthesized from the given starting material and any other necessary reagent:
Please provide a way to prepare the following compound from the given starting material.
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Chapter 12 Solutions

Pearson eText Organic Chemistry -- Instant Access (Pearson+)

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