feb_22 - 2/22/2010 Which C=O group is more reactive with...

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2/22/2010 1 Which C=O group is more reactive with LiAlH 4 ? O H 1. LiAlH 4 2. H 2 O A B 1. LiAlH 4 2. H 2 O Which C=O group is more reactive with LiAlH 4 ? O H A B 1. LiAlH 4 2. H 2 O O OCH3 E R G What is the structure of the first intermediate? OCH 3 H H Al H H H This intermediate is unstable, why? Can aldehydes be prepared LiAlH 4 reduction of esters? (A) yes (B) no O H fast slow 3 1. LiAlH 4 2. H 2 O O OCH Why does diisobutylaluminum hydride reduce esters to aldehydes but lithium aluminum does not? O H Which reducing agent is the stronger acid? O H O OCH 3 1. H-Al( i -Bu) 2 2. H 2 O H Al H Al H H H O OCH 3 O OCH 3 A B Why does diisobutylaluminum hydride reduce esters but lithium aluminum does not? O H Which C=O compound is the stronger base? O H A O OCH 3 1. H-Al( -Bu) 2 2. H 2 O H Al H Al H H H O OCH 3 O OCH 3 B
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2/22/2010 2 Why does diisobutylaluminum hydride reduce esters but lithium aluminum does not? slow OH H H H-Al( i -Bu) 2 O H fast H Al O OCH 3 H-Al( -Bu) 2 O OCH 3 H Al( -Bu) 2 O OCH 3 1. H-Al( -Bu) 2 2. H 2 O fast OCH 3
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This note was uploaded on 04/06/2010 for the course CHE 326 taught by Professor Fowler during the Spring '08 term at SUNY Stony Brook.

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feb_22 - 2/22/2010 Which C=O group is more reactive with...

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