Unformatted text preview: When L = OH, there can be no displacement or elimination. Hydride is a poor nucleophile and a poor initiator of elimination reactions. But it is a great Brønsted base when it comes to deprotonations. So the reaction is the formation of the alkoxide by deprotonation of the alcohol. As H 2 is the other product, the reaction is irreversible. O H H H 2 O + In the first S N 2 - the more polar solvent makes the reaction go faster- it will stabilize the polar TS more than the nonpolar starting materials. In the second S N 2, the more polar solvent makes the reaction go slower. The more polar the solvent, the more that starting materials will be stabilized relative to the less polar TS. See Book, pp 298-299 for diagrams....
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- Fall '10
- pH, Nucleophilic substitution, good leaving group, Hofmann