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Chemistry / Organic Chemistry 7 / Chapter 10 / Problem 53P

Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice

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Chapter 10, Problem 53P

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QUESTION:

Problem 53P

Draw the elimination products for each of the following reactions; if the products can exist as stereoisomers, indicate which stereoisomers are obtained.

a. (2S,3S)-2-chloro-3-methylpentane + high concentration of CH3O-

b. (2S,3R)-2-chloro-3-methylpentane + high concentration of CH3O-

c. (2R,3S)-2-chloro-3-methylpentane + high concentration of CH3O-

d. (2R,3R)-2-chloro-3-methylpentane + high concentration of CH3O-

e. 3-chloro-3-ethyl-2,2-dimethylpentane + high concentration of CH3CH2O-

Questions & Answers

QUESTION:

Problem 53P

Draw the elimination products for each of the following reactions; if the products can exist as stereoisomers, indicate which stereoisomers are obtained.

a. (2S,3S)-2-chloro-3-methylpentane + high concentration of CH3O-

b. (2S,3R)-2-chloro-3-methylpentane + high concentration of CH3O-

c. (2R,3S)-2-chloro-3-methylpentane + high concentration of CH3O-

d. (2R,3R)-2-chloro-3-methylpentane + high concentration of CH3O-

e. 3-chloro-3-ethyl-2,2-dimethylpentane + high concentration of CH3CH2O-

ANSWER:

Solution 53P

Step 1 of 4

(a)

The provided reactants are (2S, 3S)-2-chloro-3-methylpentane and high concentration of methoxide ion. In this reaction the nucleophile is a strong nucleophile so reaction takes place through reaction mechanism.

The alkyl halide (2S, 3S)-2-chloro-3-methylpentane undergoes reaction with methoxideion to form (E)-3-methylpent-2-ene.

The reaction is as follows:

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