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Compound A is an optically active alcohol. Treatment with

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

Solution for problem 52SP Chapter 11

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 52SP

Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3 converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4-dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.

Step-by-Step Solution:
Step 1 of 3

Solution 52SP

        The structure of product A through E is given below -

Step 2 of 3

Chapter 11, Problem 52SP is Solved
Step 3 of 3

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

Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The answer to “Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3 converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4-dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.” is broken down into a number of easy to follow steps, and 88 words. Since the solution to 52SP from 11 chapter was answered, more than 281 students have viewed the full step-by-step answer. This full solution covers the following key subjects: compound, reagent, solution, Grignard, initial. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The full step-by-step solution to problem: 52SP from chapter: 11 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8.

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