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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

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

Organic Chemistry | 8th Edition

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Problem 21P

Under appropriate conditions, (S)-1-bromo-1-fluoroethane reacts with sodium methoxide to givepure (S)-1-fluoro-1-methoxyethane.

(a) Why is bromide rather than fluoride replaced?

(b) Draw perspective structures (as shown on the previous page for 2-bromobutane) for thestarting 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 SN2 mechanism?

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...

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 1323 students have viewed the full step-by-step answer. The answer to “Under appropriate conditions, (S)-1-bromo-1-fluoroethane reacts with sodium methoxide to givepure (S)-1-fluoro-1-methoxyethane. (a) Why is bromide rather than fluoride replaced?(b) Draw perspective structures (as shown on the previous page for 2-bromobutane) for thestarting 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 SN2 mechanism?” is broken down into a number of easy to follow steps, and 59 words.

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

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