Week_5.4_PurpleBook_Answers

Week_5.4_PurpleBook_Answers - 134 Special Hydride...

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O OH O OH O OH O OH O OH HN OCH 3 CH 3 O OCH 3 OH (after H + workup) O N H CH 3 N H CH 3 O OCH 3 Special Hydride Reductions: Synthesizing Aldehydes O H The DIBAL will react with the ester to form a stable tetrahedral intermediate which, upon workup, yields the aldehyde. The tetrahedral intermediate is stabilized by the Weinreb amide, so that, after workup, an aldehyde is produced. 1. Provide the intermediates and products of the following reaction sequences. O N OCH 3 CH 3 OH, H + CH 3 N OCH 3 2. Provide the internediates and products of the following special reaction sequences. What makes these reactions different? CH 3 CH 3 OH, H + H 1. SOCl 2 2. CH 3 NH 2 O DIBAL AlH 2 1. SOCl 2 2. H + workup (after H + workup) O H H O Al( i Bu) 2 OCH 3 (after H + workup) H + workup OH (Weinreb amide) LiAlH 4 LiAlH 4 LiAlH 4 LiAlH 4 Week 5 134
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O OH O OH O OH O OH O OH HN OCH 3 CH 3 O O O OCH 3 CH 3 HO CH 3 O N H CH 3 O N CH 3 Special Organometallic Additions: Synthesizing Ketones O Cl 1. Provide the intermediates and products of the following reaction sequences.
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This note was uploaded on 05/01/2008 for the course CHEM 51 taught by Professor Gribble during the Spring '08 term at Dartmouth.

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Week_5.4_PurpleBook_Answers - 134 Special Hydride...

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