×
Log in to StudySoup
Get Full Access to Organic Chemistry - 8 Edition - Chapter 6 - Problem 36p
Join StudySoup for FREE
Get Full Access to Organic Chemistry - 8 Edition - Chapter 6 - Problem 36p

Already have an account? Login here
×
Reset your password

Under second-order conditions (strong base nucleophile),

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 36P Chapter 6

Organic Chemistry | 8th Edition

  • Textbook Solutions
  • 2901 Step-by-step solutions solved by professors and subject experts
  • Get 24/7 help from StudySoup virtual teaching assistants
Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

4 5 1 256 Reviews
15
2
Problem 36P

Problem 36P

Under second-order conditions (strong base nucleophile), SN2and E2 reactions may occur simultaneously and compete with each other. Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2° alkyl halide) with sodium ethoxide.

Step-by-Step Solution:

Solution 36P:

Here we are going to write the reaction  of 2-bromo-3-methylbutane (a moderately hindered 2° alkyl halide) with sodium ethoxide with dominant product formation.

Step 1:

With a strong base, either the SN2 or the E2 (second order elimination)  reaction is possible. Here, the reaction is as follows:

The E2 reaction requires abstraction of a proton on a carbon atom next to the carbon bearing the halogens. Thus in 2-bromo-3-methylbutane ,  there are two or more possibilities, mixtures of products may result. It follows the Zaitsev’s rule where more substituted alkene is the major product.

On the other hand,

Since, sodium ethoxide is a strong base as well as strong nucleophile. In the E2 reaction just shown, ethoxide reacts as a base rather than as a nucleophile. Most strong nucleophiles are also strong bases, and elimination commonly results when a strong base nucleophile is used with a poor substrate such as a 3° or hindered 2° alkyl halide. Thus the SN2 mechanism is blocked because the secondary alkyl halide is too hindered.

Step 2 of 1

Chapter 6, Problem 36P is Solved
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 answer to “Under second-order conditions (strong base nucleophile), SN2and E2 reactions may occur simultaneously and compete with each other. Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2° alkyl halide) with sodium ethoxide.” is broken down into a number of easy to follow steps, and 37 words. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. Since the solution to 36P from 6 chapter was answered, more than 764 students have viewed the full step-by-step answer. This full solution covers the following key subjects: Alkyl, base, bromo, compete, conditions. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The full step-by-step solution to problem: 36P from chapter: 6 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM.

Other solutions

People also purchased

Related chapters

Unlock Textbook Solution

Enter your email below to unlock your verified solution to:

Under second-order conditions (strong base nucleophile),