Give the structures of the intermediates and products V through Z.

Short Answer

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Alcohol that is made up of a five-membered ring with one OH group is cyclopentanol. This compound is colorless and exists in the liquid state at room temperature.

Step by step solution

01

About cyclopentanol

Alcohol that is made up of a five-membered ring with one OH group is cyclopentanol. This compound is colorless and exists in the liquid state at room temperature.

02

About the reaction

The reaction of cyclopentanol with PB3 gives bromocyclopentane. Therefore, product W is bromocyclopentane. When bromocyclopentane is treated with magnesium in the presence of ether, cyclopentylmagnesium bromide is obtained. Therefore, product X is cyclopentylmagnesium bromide. The reaction of cyclopentanol with Na2Cr2O7and H2SO4gives cyclopentanone. Thus, product V is cyclopentanone.

03

About the reaction

The cyclopentylmagnesium bromide reacts with cyclopentanone to give [1,1'-bi(cyclopentan)]-1-ol. Therefore, the product Y is [1,1'-bi(cyclopentan)]-1-ol. The reaction of [1,1'-bi(cyclopentan)]-1-ol with acetyl chloride gives [1,1'-bi(cyclopentan)]-1-yl acetate. Thus, the product Z is [1,1'-bi(cyclopentan)]-1-yl acetate.

The chemical reaction is shown below.

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Most popular questions from this chapter

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent

(a) butan - 1 - ol → butanal, CH3CH2CH2CHO

(b) but - 2 - en - 1 - ol → but - 2 - enoic acid, CH3CH = CHCOOH

(c) butan - 2 - ol → butan - 2 - one, CH3COCH2CH3

(d) cyclopentanol → 1 - cyclopentylpropan - 1 - ol (twosteps)

(e) cyclopentyclohexanol → 2 - methylcyclohexanone (several steps)

(f) 1 - methylcyclohexanol → 2 - methylcyclohexanone (several steps)

Two products are observed in the following reaction.

(a) Suggest a mechanism to explain how these two products are formed.

(b) Your mechanism for part (a) should be different from the usual mechanism of the reaction of SOCl2 with alcohols. Explain why the reaction follows a different mechanism in

this case.

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.

Predict the products of the reactions of the following compounds with:

(1) chromic acid or excess sodium hypochlorite with acetic acid.

(2)PCC or NaOCl (1 equivalent) with TEMPO.

(a)cyclohexanol (b)1-methylcyclohexanol

(c)cyclopentylmethanol (d)cyclohexanone

(e)cyclohexane (f)1-phenylpropan-1-ol

(g)hexan-1-ol (h)acetaldehyde, CH3CHO

Neopentyl alcohol, (CH3)3CCH2OH, reacts with concentrated HBr to give 2-bromo-2-methylbutane, a rearranged product. Propose a mechanism for the formation of this product.

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