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Chapter 11: Q11-70E (page 350)

(S)-2-Butanol slowly racemizes on standing in dilute sulfuric acid. Explain.

Short Answer

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Mechanism for the reaction

Step by step solution

01

Secondary alcohol

Since 2-butanol is a secondary alcohol, substitution can occur by either an SN1orSN2route, depending on reaction conditions. Two factors favor aSN1mechanism in this case. The reaction is run under solvolysis (solvent as a nucleophile) conditions in a polar, protic solvent. Dilute acid converts a poor leaving groupOH- into a good leaving groupdata-custom-editor="chemistry" OH2which dissociates easily.

02

Explanation

Initially, there is protonation of the hydroxyl oxygen, which is then followed by a loss of water to form a planar carbocation. Finally, an attack of water from either side of the planar carbocation yields a racemic product.

Mechanism for the reaction

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Most popular questions from this chapter

How might you prepare each of the following molecules using a nucleophilic substitution reaction at some step?

(a)

Question:What products would you expect from the reaction of 1-bromopropane with each of the following?

(a) NaNH2

Predict the product of each reaction below and indicate if the mechanism is likely to beSN1,SN2,E1,E2orE1cB

Organic solvents like benzene, ether, and chloroform are neither protic nor strongly polar. What effect would you expect these solvents to have on the reactivity of a nucleophile in SN2 reactions?

Treatment of 1-bromo-2-deuterio-2-phenylethane with strong base leads to a mixture of deuterated and nondeuterated phenylethylenes in an approximately 7;1 ratio. Explain
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