×
Log in to StudySoup
Get Full Access to Chemistry - Textbook Survival Guide
Join StudySoup for FREE
Get Full Access to Chemistry - Textbook Survival Guide

Draw a perspective structure or a Fischer projection for

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

Solution for problem 20P 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 1 355 Reviews
29
0
Problem 20P

Draw a perspective structure or a Fischer projection for the products of the following SN2 reactions.

(a) trans-1-bromo-3-methylcyclopentane + KOH

(b) ( R ) - 2 -bromopentane + KCN

(c)

(d)

(e)

(f)

Step-by-Step Solution:
Step 1 of 3

Solution 20P

(a)

Trans-1-bromo-3-methyl cyclopentane undergoes SN2 displacement by hydroxide ion. Inversion of configuration gives cis-3-methylcyclopentanol.

The reaction is as follows:

(b)

The bromide ion leaves with a pair of electrons, followed by attack of cyanide ion from back side to form (S)-2-methylpentanenitrile.

The stereochemistry of the product is inverted. The reaction is as follows:

(c)

(2R, 3R)-2-bromo-3-methylpentane undergoes SN2 displacement by iodide ion. Inversion of configuration at C2 gives (2S, 3R)-2-iodo-3-methylpentane.

The reaction is as follows:

(d)

(S)-2-bromo-1-fluoroethane...

Step 2 of 3

Chapter 6, Problem 20P is Solved
Step 3 of 3

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

Unlock Textbook Solution

Enter your email below to unlock your verified solution to:

Draw a perspective structure or a Fischer projection for

×
Log in to StudySoup
Get Full Access to Chemistry - Textbook Survival Guide
Join StudySoup for FREE
Get Full Access to Chemistry - Textbook Survival Guide
×
Reset your password