×
Log in to StudySoup
Get Full Access to Organic Chemistry - 8 Edition - Chapter 6 - Problem 21p
Join StudySoup for FREE
Get Full Access to Organic Chemistry - 8 Edition - Chapter 6 - Problem 21p

Already have an account? Login here
×
Reset your password

Under appropriate conditions, (S)-1-bromo-1-fluoroethane

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

Solution for problem 21P 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 1 339 Reviews
16
0
Problem 21P

Under appropriate conditions,  -bromo- 1 -fluoroethane reacts with sodium methoxide to give  and  are just names. Don'tpure  -fluoro-1-methoxyethane. rely on names to determine the stereochemistry of a reaction

                                                      

(a) Why is bromide rather than fluoride replaced?(b) Draw perspective structures (as shown on the previous page for 2 -bromobutane) for the starting material, the transition state, and the product.(c) Does the product show retention or inversion of configuration?(d) Is this result consistent with reaction by the  mechanism?

Problem-solving Hint

(R) and (S) are just names. Don’t rely on names to determine the stereochemistry of a reaction.

Step-by-Step Solution:
Step 1 of 3

Solution 21P

(a)

 In the given substrate, the carbon-fluorine bond is very polar. Fluoride ion is a poor leaving group for the same reason that hydrofluoric acid is only a weak acid. The fluoride ion is too small to stably support a full negative charge. The best halide leaving groups are the conjugate bases of the strongest acids.

Bromine is good leaving group than fluorine.

(b)

The mechanism of the reaction is:

(c)

The configuration of the reactant and product are  -configuration. But, here inversion is takes place. In the above reaction, the oxygen of the product has a lower priority than the bromine it replaces. So, the product getting also -configuration.

(d)

This result is in consistent with 2 mechanism. Even though both the reactant and the product have the  designation, the configuration has been inverted: the nomenclature priority of fluorine changes from second (after bromine) in the reactant to first (before oxygen) in the product. While the designation may be misleading, the structure shows with certainty that an inversion has occurred.

Step 2 of 3

Chapter 6, Problem 21P is Solved
Step 3 of 3

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

The full step-by-step solution to problem: 21P from chapter: 6 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. This full solution covers the following key subjects: Product, perspective, bromo, bromobutane, conditions. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Since the solution to 21P from 6 chapter was answered, more than 1929 students have viewed the full step-by-step answer. The answer to “?Under appropriate conditions, -bromo- 1 -fluoroethane reacts with sodium methoxide to give and are just names. Don'tpure -fluoro-1-methoxyethane. rely on names to determine the stereochemistry of a reaction (a) Why is bromide rather than fluoride replaced?(b) Draw perspective structures (as shown on the previous page for 2 -bromobutane) for the starting material, the transition state, and the product.(c) Does the product show retention or inversion of configuration?(d) Is this result consistent with reaction by the mechanism?Problem-solving Hint (R) and (S) are just names. Don’t rely on names to determine the stereochemistry of a reaction.” is broken down into a number of easy to follow steps, and 94 words.

Other solutions

People also purchased

Related chapters

Unlock Textbook Solution

Enter your email below to unlock your verified solution to:

Under appropriate conditions, (S)-1-bromo-1-fluoroethane