0243Pb44an-09.cwk (WP)

0243Pb44an-09.cwk (WP) - from the rear of the departing...

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Answers to Problem 44, Chemistry 0243 - 2009 Sodium hydride will remove the OH proton to give a pair of stereoisomeric alkoxides. One of these can undergo an intramolecular S N 2 reaction to give C 5 H 8 O, but the other cannot, as in only one stereoisomer is the nucleophile positioned properly to do the displacement
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Unformatted text preview: from the rear of the departing bond. There are NO frontside S N 2 reactions known. OH I H H OH H I OH H H NaH NaH Na + Na + H O I H I O H C 5 H 8 I ONa C 5 H 8 I ONa H O H C 5 H 8 O two compounds = and squiggley line means stereochemistry not specified – and – S N 2 no S N 2 possible H I...
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