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Chapter 11: Q15P (page 559)

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.

Short Answer

Expert verified

Neopentyl alcohol(CH3)3CCH2OHis a primary alcohol, but the bulky group has hinderedit. The backside attack is not possible, so instead of the SN2 mechanism SN1followedto get the desired rearranged product.

The reaction forms a rearranged stable carbocation from primary carbocation to tertiary carbocation.

Step by step solution

01

Step 1: Rearranged Product

Neopentyl alcohol(CH3)3CCH2OHis a primary alcohol, but the bulky group has hinderedit. The backside attack is not possible, so instead of the SN2 mechanism SN1followedto get the desired rearranged product.

The reaction forms a rearranged stable carbocation from primary carbocation to tertiary carbocation.

02

 Mechanism for the formation of 2-bromo-2-methylbutane

Protonation of Neopentyl alcoholconverts the hydroxy group to a good leaving group.

Water leaves form a primary carbocation rearranged through methyl shift, thus forming a stable tertiary carbocation.

Bromide ion attacks the carbocation to form the product 2-bromo-2-methylbutane

Mechanism showing the formation of 2-bromo-2-methylbutane

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Most popular questions from this chapter

The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.

(a)1 equivalent of NaH, followed by 1 equivalent of CH3l and heat

(b)2 equivalents of NaH, followed by 2 equivalents of CH3l and heat

(c) 3 equivalents of NaH, followed by 3 equivalents of CH3l and heat

Propose a mechanism for the reaction of

(a) 1-methyl cyclohexanol with HBr to form 1- bromo-1-methylcyclohexane.

(b) 2- cyclohexylethanol with HBr to form 1-bromo-2-cyclohexylethane.

Predict the major products of the following reactions.

(a)ethyl tosylate+potassium tert-butoxide

(b) isobutyl tosylate + NaI

(c) (R)-2-hexyl tosylate + NaCN

(d) the tosylate of cyclohexylmethanol +excess NH3

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?

Give the structures of the products you would expect when each alcohol reacts with

(1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P/I2; and (5) SOCl2.

(a) butan-1-ol (b) 2-methylbutan-2-ol

(c) 2,2-dimethylbutan-1-ol (d) cis-3-methylcyclopentanol
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