Draw the configuration(s) of the substitution product(s)

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

Problem 24P Chapter 9

Organic Chemistry | 7th Edition

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

Organic Chemistry | 7th Edition

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Problem 24P

Draw the configuration(s) of the substitution product(s) that will be formed from the reactions of the following compounds with the indicated nucleophile:

Step-by-Step Solution:

Solution 24P

Step 1 of 5</p>

Substitution reactions are the organic reactions in which a substituent in a molecule is replaced by another substituent. This reaction can proceed with one step mechanism or a reaction with two step mechanism. The one step reaction is called  and two steps reaction is called. The kinetics of the reaction is unimolecular in case of bimolecular in.

The rate of is dependent on both reactants and the rate of  is dependent on only alkyl halide molecule. In, a carbocation is formed first and then attack of nucleophile takes place whereas in, attack of nucleophile and detachment of existing substituent takes place simultaneously.

Step 2 of 5</p>

(a)

The reaction of  with ammonia is  reaction. Because of high concentration of a good nucleophile that is ammonia, the reaction takes place through  mechanism. The nucleophile attacks the carbon atom on the opposite side of the leaving group resulting in the inversion of the configuration at the stereocenter. It is represented as follows:

Step 3 of 5</p>

(b)

The reactant is a tertiary alkyl halide. It is an example of  reaction. The carbon atom is attacked by nucleophile on the reverse side of leaving group and configuration of carbon atom becomes opposite to that of original molecule. This process is called inversion of stereochemistry. In  reactions, the intermediate is carbocation. As carbocation is planar the nucleophile attacks the two faces of the planar cation and gives the product with exactly equal proportion of -isomer and -isomer. It is said to be racemic mixture. It is represented as follows:

Step 4 of 5

Chapter 9, Problem 24P is Solved
Step 5 of 5

Textbook: Organic Chemistry
Edition: 7
Author: Paula Yurkanis Bruice
ISBN: 9781269406772

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