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Chapter 11: Q47P (page 588)

When 1-cyclohexylethanol is treated with concentrated aqueous, the major product is 1-bromo-1-ethylcyclohexane.

(a)Propose a mechanism for this reaction.

(b) How would you convert 1-cyclohexylethanol to (1-bromoethyl)cyclohexane in good yield?

Short Answer

Expert verified

a.Mechanism of 1-bromo-1-ethylcyclohexane

b.

Step by step solution

01

Synthesis

1-bromo-1-ethylcyclohexane is synthesized from1-cyclohexylethanol. It is a secondary alcohol, so it is treated with conc. aqu.to form 1-bromo-1-ethylcyclohexane.

02

(a)  Mechanism

1-cyclohexylethanol is treated with forms a compound and removal of water molecule takes place forms carbocation and then to carbocation. attack to carbocation to form 1-bromo-1-ethylcyclohexane.

Mechanism of 1-bromo-1-ethylcyclohexane

03

Step 3:b. Reagent used

To convert 1-cyclohexylethanol to (1-bromoethyl) cyclohexane phosphorous tribromide(PBr3) is used as a reagent.

04

Step 4:b. Synthesis of (1-bromoethyl) cyclohexane

1-cyclohexylethanol is treated with phosphorous tribromide to form (1-bromoethyl) cyclohexane.

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