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In a laboratory are found two different compounds: A (melting point 24.7 C) and B

Organic Chemistry | 6th Edition | ISBN: 9781936221349 | Authors: Marc Loudon, Jim Parise

Problem 10.58 Chapter 10

Organic Chemistry | 6th Edition

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Organic Chemistry | 6th Edition | ISBN: 9781936221349 | Authors: Marc Loudon, Jim Parise

Organic Chemistry | 6th Edition

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Problem 10.58

In a laboratory are found two different compounds: A (melting point 24.7 C) and B (melting point 21 C). Both compounds have the same molecular formula (C7H14O), and both can be resolved into enantiomers. Both compounds give off a gas when treated with NaH. Treatment of either A or B with tosyl chloride in pyridine yields a tosylate ester, and treatment of either tosylate with potassium tert-butoxide gives a mixture of the same two alkenes, C and D. However, reaction of the tosylate of A with potassium tert-butoxide to give these alkenes is noticeably slower than the corresponding reaction of the tosylate of B. When either optically active A or optically active B is subjected to the same treatment, both alkene products C and D are optically active. Treatment of either C or D with H2 over a catalyst yields methylcyclohexane. Identify all unknown compounds and explain your reasoning

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Lecture1:08/30/2017 Tuesday,August29,2017 8:07PM • WhatisChemistry ○ Thestudyofthecomposition,propertiesandtransformationsofmatter • Twofundamentalpropertiesofmatter ○ Physical § Transformationswhichdonotalterchemicalnatureofthematter (e.g.phasechanges) Suchassize,color,mass,density,meltingpoint,etc....

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Chapter 10, Problem 10.58 is Solved
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Textbook: Organic Chemistry
Edition: 6
Author: Marc Loudon, Jim Parise
ISBN: 9781936221349

Organic Chemistry was written by and is associated to the ISBN: 9781936221349. This full solution covers the following key subjects: . This expansive textbook survival guide covers 239 chapters, and 1693 solutions. The answer to “In a laboratory are found two different compounds: A (melting point 24.7 C) and B (melting point 21 C). Both compounds have the same molecular formula (C7H14O), and both can be resolved into enantiomers. Both compounds give off a gas when treated with NaH. Treatment of either A or B with tosyl chloride in pyridine yields a tosylate ester, and treatment of either tosylate with potassium tert-butoxide gives a mixture of the same two alkenes, C and D. However, reaction of the tosylate of A with potassium tert-butoxide to give these alkenes is noticeably slower than the corresponding reaction of the tosylate of B. When either optically active A or optically active B is subjected to the same treatment, both alkene products C and D are optically active. Treatment of either C or D with H2 over a catalyst yields methylcyclohexane. Identify all unknown compounds and explain your reasoning” is broken down into a number of easy to follow steps, and 149 words. Since the solution to 10.58 from 10 chapter was answered, more than 213 students have viewed the full step-by-step answer. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 6. The full step-by-step solution to problem: 10.58 from chapter: 10 was answered by , our top Chemistry solution expert on 03/16/18, 03:35PM.

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