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Like other strong nucleophiles, triphenylphosphine attacks

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

Solution for problem 14P Chapter 18

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 14P

Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide.

(a) Show each step in the reaction of trans-2,3-epoxybutane with triphenylphosphine to give but-2-ene. What is the stereochemistry of the double bond in the product?

(b) Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.

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Solution 14P

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Chapter 18, Problem 14P is Solved
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Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

The full step-by-step solution to problem: 14P from chapter: 18 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. Since the solution to 14P from 18 chapter was answered, more than 377 students have viewed the full step-by-step answer. This full solution covers the following key subjects: triphenylphosphine, stereochemistry, cyclooctene, Product, might. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The answer to “Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide.(a) Show each step in the reaction of trans-2,3-epoxybutane with triphenylphosphine to give but-2-ene. What is the stereochemistry of the double bond in the product?(b) Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.” is broken down into a number of easy to follow steps, and 63 words.

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Like other strong nucleophiles, triphenylphosphine attacks