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Chapter 20: Q19P (page 1038)

Suggest how you would convert trans-4-methylcyclohexanol to

(a) trans-1-chloro-4-methylcyclohexane.

(b) cis-1-chloro-4-methylcyclohexane.

Short Answer

Expert verified

(a)

(b)

Step by step solution

01

Step 1: Chemical Reaction of Alcohols

Alcohol, while showing their chemical change, act as a 鈥渧ersatile鈥� organic compound. It can act both as a nucleophile (Nu- ) as well as an electrophile(E+ ).

The chemical reaction of Alcohols are of two types:

  • Reaction involving cleavage of O-H bond

  • Reaction involving cleavage of C-OH bond

02

 Conversion of reactant trans-4-methyl cyclohexanol to given products

  1. trans-4-methyl cyclohexanol, when reacting withThionyl chloride (SOCl2), is the best reagent for converting an alcohol to an alkyl chloride and as the by-products (gaseous SO2 and HCl) leave the reaction mixture and ensure there can be no reverse reaction. Thus the trans-4-methyl cyclohexanol has been converted to trans-1-chloro-4-methylcyclohexane when reacted with Thionyl chloride (SOCl2).

Conversion of trans-4-methyl cyclohexanol to trans-1-chloro-4-methylcyclohexane

b. trans-4-methyl cyclohexanol, when reacted with tosyl chloride (TsCl) in the presence of pyridine, forms the tosylate ester. Tosylate ester reacts with sodium chloride (NaCl) shows SN2 displacement of tosylate ion forms the tosylate ester with inversion of configuration leading to the formation of cis 1-chloro-4-methylcyclohexane.

c. Conversion of trans-4-methyl cyclohexanol to cis 1- chloro-4-methylcyclohexane

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Most popular questions from this chapter

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