Arrange the following alkyl halides in order from most

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

Problem 18P 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 18P

Arrange the following alkyl halides in order from most reactive to least reactive in an SN1 reaction: 2-bromo-2-methylpentane, 2-chloro-2-methylpentane, 3-chloropentane, and 2-iodo-2-methylpentane.

Step-by-Step Solution:

Solution 18P

Step 1 of 5</p>

Elimination reactions are a class of organic reactions in which two substituents are removed from a molecule. This removal can be a reaction with one step mechanism or a reaction with two step mechanism. The one step reaction is called E2 reaction and two steps reaction is called E1 reaction.

The rate of an E1 reaction is dependent on both reactants that are a base and alkyl halide. In this only a strong base is capable of extracting weakly acidic hydrogen and alkyl halide should be primary substituted. The rate of an E2 reaction is dependent on only alkyl halide molecule. In this presence of a base is not affecting the reaction as the alkyl halide is able to loose hydrogen on its own. Thus, presence of a weak base and tertiary alkyl halide is favored in case of E2 reaction.

Step 2 of 5</p>

(a)

The substrate, trans-1-chloro-2-methylcyclohexane, is a secondary alkyl halide and the nucleophile is methoxide ion, , which is a strong base. So, the reaction of methoxide ion with trans-1-chloro-2-methylcyclohexane gives the following products:

Step 3 of 5</p>

(b)

The substrate, trans-1-chloro-2-methylcyclohexane, is a secondary alkyl halide and the nucleophile is methoxide ion, , which is a strong base. So, the reaction of methoxide ion with cis-1-chloro-2-methylcyclohexane gives the following products:

Step 4 of 5

Chapter 9, Problem 18P is Solved
Step 5 of 5

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

The answer to “Arrange the following alkyl halides in order from most reactive to least reactive in an SN1 reaction: 2-bromo-2-methylpentane, 2-chloro-2-methylpentane, 3-chloropentane, and 2-iodo-2-methylpentane.” is broken down into a number of easy to follow steps, and 22 words. This full solution covers the following key subjects: methylpentane, reactive, iodo, chloro, chloropentane. This expansive textbook survival guide covers 30 chapters, and 2818 solutions. The full step-by-step solution to problem: 18P from chapter: 9 was answered by Sieva Kozinsky, our top Chemistry solution expert on 09/04/17, 10:07PM. Since the solution to 18P from 9 chapter was answered, more than 346 students have viewed the full step-by-step answer. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 7. Organic Chemistry was written by Sieva Kozinsky and is associated to the ISBN: 9781269406772.

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