If an alcohol were to undergo a substitution reaction, which of the following modifications would improve the alcohol's leaving group ability?A.Protection of the alcoholB.Deprotonation of the alcoholC.Conversion of the alcohol to a mesylateD.Oxidation of the alcohol
Question
If an alcohol were to undergo a substitution reaction, which of the following modifications would improve the alcohol's leaving group ability?A.Protection of the alcoholB.Deprotonation of the alcoholC.Conversion of the alcohol to a mesylateD.Oxidation of the alcohol
Solution
The modification that would improve the alcohol's leaving group ability in a substitution reaction is C. Conversion of the alcohol to a mesylate.
Here's why:
A. Protection of the alcohol: This would not improve the leaving group ability. Protection of the alcohol is usually done to prevent it from reacting, not to enhance its reactivity.
B. Deprotonation of the alcohol: This would not improve the leaving group ability. Deprotonation of the alcohol would result in an alkoxide, which is a strong base and a poor leaving group.
C. Conversion of the alcohol to a mesylate: This would improve the leaving group ability. Mesylates are excellent leaving groups because they are stable ions. The mesyl group (SO3CH3) is electron-withdrawing, which stabilizes the negative charge that develops on the oxygen in the transition state of the reaction.
D. Oxidation of the alcohol: This would not improve the leaving group ability. Oxidation of an alcohol results in a carbonyl compound, which does not have a good leaving group.
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