Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
Question
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Chapter 10.11, Problem 34P

(a)

Interpretation Introduction

Interpretation:

A multi-step synthesis has to be designed for the given conversion.

Concept Introduction:

Target molecule is nothing but the desired product.

Adding HBr to alkene forms a compound with a leaving group that can be replaced by a nucleophile.

The elimination reaction should be carried out under SN2 condition i.e. with strong nucleophile. So there will be no compensating substitution reaction.

The bulky base is used in the elimination reaction to maximize the amount of elimination product.

To prepare cyclic ether, the alkyl halide and alcohol must be a part of the same molecule.

Addition of water to the given starting material creates bifunctional compound.

(b)

Interpretation Introduction

Interpretation:

A multi-step synthesis has to be designed for the given conversion.

Concept Introduction:

Target molecule is nothing but the desired product.

Adding HBr to alkene forms a compound with a leaving group that can be replaced by a nucleophile.

The elimination reaction should be carried out under SN2 condition i.e. with strong nucleophile.  So there will be no compensating substitution reaction.

The bulky base is used in the elimination reaction to maximize the amount of elimination product.

To prepare cyclic ether, the alkyl halide and alcohol must be a part of the same molecule.

Addition of water to the given starting material creates bifunctional compound.

(c)

Interpretation Introduction

Interpretation:

A multi-step synthesis has to be designed for the given conversion.

Concept Introduction:

Target molecule is nothing but the desired product.

Organic Chemistry, Chapter 10.11, Problem 34P Adding HBr to alkene forms a compound with a leaving group that can be replaced by a nucleophile.

The elimination reaction should be carried out under SN2 condition i.e. with strong nucleophile. So there will be no compensating substitution reaction.

The bulky base is used in the elimination reaction to maximize the amount of elimination product.

To prepare cyclic ether, the alkyl halide and alcohol must be a part of the same molecule.

Addition of water to the given starting material creates bifunctional compound.

(d)

Interpretation Introduction

Interpretation:

A multi-step synthesis has to be designed for the given conversion.

Concept Introduction:

Target molecule is nothing but the desired product.

Adding HBr to alkene forms a compound with a leaving group that can be replaced by a nucleophile.

The elimination reaction should be carried out under SN2 condition i.e. with strong nucleophile. So there will be no compensating substitution reaction.

The bulky base is used in the elimination reaction to maximize the amount of elimination product.

To prepare cyclic ether, the alkyl halide and alcohol must be a part of the same molecule.

Addition of water to the given starting material creates bifunctional compound.

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Chapter 10 Solutions

Organic Chemistry

Ch. 10.4 - Prob. 11PCh. 10.5 - Prob. 12PCh. 10.6 - Prob. 14PCh. 10.7 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 10.7 - Which isomer reacts more rapidly in an E2...Ch. 10.7 - Prob. 18PCh. 10.8 - Prob. 19PCh. 10.8 - Prob. 20PCh. 10.9 - Prob. 21PCh. 10.9 - Explain why only a substitution product and no...Ch. 10.9 - Prob. 23PCh. 10.9 - Prob. 24PCh. 10.9 - Prob. 25PCh. 10.9 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 10.10 - A small amount of another organic product is...Ch. 10.10 - What is the best way to prepare the following...Ch. 10.10 - Prob. 29PCh. 10.10 - Prob. 30PCh. 10.10 - Why is a cumulated diene not formed in the...Ch. 10.10 - What product is obtained when the following...Ch. 10.11 - Prob. 33PCh. 10.11 - Prob. 34PCh. 10 - Draw the major product obtained when each of the...Ch. 10 - Prob. 36PCh. 10 - a. Indicate how each of the following factors...Ch. 10 - Prob. 38PCh. 10 - A chemist wanted to synthesize the...Ch. 10 - Prob. 40PCh. 10 - Prob. 41PCh. 10 - Prob. 42PCh. 10 - Starting with an alkyl halide, how could the...Ch. 10 - Indicate which species in each pair gives a higher...Ch. 10 - Prob. 45PCh. 10 - For each of the following alkyl halides, indicate...Ch. 10 - Prob. 47PCh. 10 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 10 - Prob. 49PCh. 10 - When the following compound undergoes solvolysis...Ch. 10 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 10 - Draw the substitution and elimination products.Ch. 10 - Prob. 53PCh. 10 - Prob. 54PCh. 10 - Which of the following hexachlorocyclohexanes is...Ch. 10 - Explain why the rate of the reaction of...Ch. 10 - Prob. 57PCh. 10 - Two elimination products are obtained from the...Ch. 10 - Draw the structures or the product of the obtained...Ch. 10 - How could you prepare the following compounds from...Ch. 10 - cis-4-Bromocyclohexanol and...Ch. 10 - Prob. 62PCh. 10 - Prob. 63P
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