CHM 25500 Lecture Notes - Lecture 33: Alkoxide, Leaving Group, Electrophile
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5 Aug 2015
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CHM 255 - Lecture 33 - Reactions of Alcohols
Alcohols as Sources of Nucleophiles
● An alkoxide (deprotonated alcohol) may act as a nucleophile and can attack an
alkyl halide as in the following reaction
● Reactions like this are called Williamson ether syntheses; they involve the
reaction of an alkyl halide with an alcohol to produce an ether
Alcohols as Sources of Electrophiles
● Hydroxide ions make for poor leaving groups, therefore, in order to behave as an
electrophile, alcohols must protonated to turn the hydroxyl group into water, a
much better leaving group
Dehydration of Alcohols
● Dehydration of alcohols occurs in the presence of concentrated strong acids
● Dehydration is the removal of a molecule of water from the alcohol (hydroxyl
group + hydrogen)