CHM 25500 Lecture Notes - Lecture 33: Alkoxide, Leaving Group, Electrophile

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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)
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