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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

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

(a) The reaction of butan-2-ol with concentrated aqueous HBr goes with partial racemization, giving more inversion than retention of configuration. Propose a mechanism that accounts for racemization with excess inversion.

(b)Under the same conditions, an optically active sample of trans-2-bromocyclopentanol reacts with concentrated aqueous HBr to give an optically inactive product, (racemic) trans-1,2-dibromocyclopentane. Propose a mechanism to show how this reaction goes with apparently complete retention of configuration, yet with racemization. (Hint: Draw out the mechanism of the reaction of cyclopentene with in water to give the starting material, trans-2- bromocyclopentanol. Consider how parts of this mechanism might be involved in the reaction with HBr.)

Propose a mechanism for each reaction.

(a)

(b)

Predict the products formed by periodic acid cleavage of the following diols

(a)

(b)

(c)

(d)

Write balanced equations for the three preceding reactions.
See all solutions

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