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Devise a synthesis for each compound, starting with

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

Solution for problem 52SP Chapter 10

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

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

(a) 1-methylcyclohexanol

(b) cyclohexylmethanol

(c) 1-(hydroxymethyl)cyclohexanol

(d) trans-2-methylcyclohexanol

(e) 2-chloro-1-methylcyclohexanol

(f) 1-(phenylmethyl)cyclohexanol

Step-by-Step Solution:
Step 1 of 3

Step-1

(a) Synthesis of 1-methylcyclohexanol:-

1-methylcyclohexanol can be prepared from cyclohexanone in presence of mercury acetate (Hg(OAC)2)and sodium borohydride (NaBH4)

(cyclohexanone)                      (1-methylcyclohexanol)

Step-2

(b)cyclohexylmethanol

The preparation of cyclohexylmethanol has been carried out from cyclohexanone in presence of BH3 and THF (tetrahydrofuran). It is a base catalysed reaction.

(cyclohexanone)                      (cyclohexylmethanol)

Step-3

(c) 1-(hydroxymethyl)cyclohexanol

1-(hydroxymethyl)cyclohexanol can be prepared from cyclohexanone in presence of OSO4 and H2O2.

(cyclohexanone)          (1-(hydroxymethyl)cyclohexanol)

Step-4

(d)trans-2-methylcyclohexanol

This reaction has been carried out by markownikoff;s rule. In this reaction trans-2-methylcyclohexanol has been prepared from 1-methylcyclohexene...

Step 2 of 3

Chapter 10, Problem 52SP is Solved
Step 3 of 3

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

The answer to “Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.(a) 1-methylcyclohexanol(b) cyclohexylmethanol(c) 1-(hydroxymethyl)cyclohexanol(d) trans-2-methylcyclohexanol(e) 2-chloro-1-methylcyclohexanol(f) 1-(phenylmethyl)cyclohexanol” is broken down into a number of easy to follow steps, and 21 words. The full step-by-step solution to problem: 52SP from chapter: 10 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. This full solution covers the following key subjects: methylcyclohexanol, cyclohexylmethanol, methylenecyclohexane, cyclohexanol, any. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. Since the solution to 52SP from 10 chapter was answered, more than 421 students have viewed the full step-by-step answer. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8.

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