Ch_322a_11.010

Ch_322a_11.010 - Reactions of Alcohols There are two...

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Reactions of Alcohols There are two general classes of reactions of alcohols: (1) R OH C-O bond breaking (2) RO H O-H bond breaking In (1) the hydroxyl group , or another oxygen function, is the leaving group . In (2) the alcohol acts as an acid . Alcohols as Bases/Nucleophiles alcohols react with strong acids: R O H : : + H-A strong acid R-OH 2 + + A - alkyl oxonium ion
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Alcohols as Bases/Nucleophiles The protonated alcohol function is a much better leaving group than the hydroxyl group. Nucleophiles react with the alkyl oxonium ion in S N 2 reactions: Nu: - + R-OH 2 + S N 2 Nu-R + H 2 O Symmetrical ethers are produced from alcohols in the presence of strong acids: ROH + HA R-OH 2 + + A - ROH + R-OH 2
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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Ch_322a_11.010 - Reactions of Alcohols There are two...

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