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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

What effect would you expect the following changes to have on the rate of the reaction of ethanol with 2-iodo-2-methyl butane?

(a) The concentration of the halide is tripled.


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

(e) Na+-C≡CH

Question: (R)-2-Bromooctane undergoes racemization to give (±)-2-bromooctane when treated with NaBr in dimethyl sulfoxide. Explain.

Question: Order each of the following sets of compounds with respect to reactivity:

c. CH3CH2 CH2OCH3 CH3CH2 CH2OTs CH3CH2 CH2Br

d) Tell whether each of the following reactions is likely to be SN1, SN2, E1, E1cB or E2:
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