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Devise a synthesis for each compound, starting with

Chapter 2, Problem 52SP

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QUESTION:

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

Questions & Answers

QUESTION:

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

ANSWER:

Solution:

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)

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