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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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Most popular questions from this chapter

The Williamson ether synthesis involves the displacement of an alkyl halide or tosylate by an alkoxide ion. Would the synthesis shown be possible by making a tosylate and displacing it? If so, show the sequence of reactions. If not, explain why not and show an alternative synthesis that would be more likely to work.

Propose mechanisms for the following reactions. In most cases, more products are formed than are shown here. You only need to explain the formation of the products shown, however.

Explain the products observed in the following reaction of an alcohol with the Lucas reagent.

Show the alcohol and the acid chloride that combine to make the following esters.

(a)

(b)

(c)

(d)

Show how you would use a simple chemical test to distinguish between the following pairs of compounds. Tell what you would observe with each compound.

(a)isopropyl alcohol andtert-butyl alcohol

(b)isopropyl alcohol and butan-2-one, CH3COCH2CH3

(c)hexan-1-ol and cyclohexanol

(d)allyl alcohol and propan-1-ol

(e)butan-2-one andtert-butyl alcohol
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