Predict the products and mechanisms of the following

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Problem 40P Chapter 6

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 40P

Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.

Step-by-Step Solution:
Step 1 of 3

Solution 40P

(a)

1-bromohexane is a primary alkyl halide and in presence of a strong base (sodium ethoxide) it mainly undergoes SN2 and possibly E2.

1- bromohexane + Nain 2

                        ethanol                (and possibly E2)

Since 1-bromohexane is primary halide, so it undergoes mainly 2 and as Nais strong base, so E2 reaction may also be observed.

(b)

2-chlorohexane is secondary alkyl halide and in presence of a strong base (sodium ethoxide) it undergoes both SN2 and E2 reaction to give a mixture of products.

2-chlorohexane and E2

Na is strong nucleophile (or base), so it will force second order kinetics, either 2 or E2 and since the halide is 2º, so both can occur.

Mechanism:

(c)

2-chloro-2-methylbutane is tertiary alkyl halide and in presence of strong base (sodium ethoxide) it undergoes E2 reaction to form more substituted alkene as a major product.

This is a 3º halide, and the base is strong, so here only E2 reaction will take place.

Mechanism:

(d)

2-chloro-2-methylbutane is heated in ethanol:

2-chloro-2-methylbutane is tertiary alkyl halide and ethanol is a weak base. So, the mixture of  and...

Step 2 of 3

Chapter 6, Problem 40P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L. G. Wade Jr
ISBN: 9780321768414

This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. The full step-by-step solution to problem: 40P from chapter: 6 was answered by Sieva Kozinsky, our top Chemistry solution expert on 05/06/17, 06:41PM. This full solution covers the following key subjects: explain, likely, mechanism, mechanisms, most. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Organic Chemistry was written by Sieva Kozinsky and is associated to the ISBN: 9780321768414. Since the solution to 40P from 6 chapter was answered, more than 292 students have viewed the full step-by-step answer. The answer to “Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.” is broken down into a number of easy to follow steps, and 23 words.

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