Dolbier HW Solutions 337

Dolbier HW Solutions 337 - benzene COH O O O C H 3 C O H CH...

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Step 4: Step 5: Step 6: Step 7: 17.10 The conversion requires reduction; however, the conditions necessary (LiAlH 4 ) would also reduce the ketone carbonyl. The ketone functionality is therefore protected as the cyclic acetal. Reduction of the carboxylic acid may now be carried out. Hydrolysis to remove the protecting group completes the synthesis. CH 2 OH CH 2 OH CH 3 C O H 2 O, HCl 4-Acetylbenzyl alcohol O O C H 3 C COH O CH 2 OH 1. LiAlH 4 2. H 2 O O O C H 3 C O O C H 3 C 4-Acetylbenzoic acid COH O CH 3 C O HOCH 2 CH 2 OH p -toluenesulfonic acid,
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Unformatted text preview: benzene COH O O O C H 3 C O H CH 2 CH 3 1 O H CH 2 CH 3 1 C 6 H 5 CH O 1 1 C 6 H 5 CH O H H O H CH 2 CH 3 1 1 O H CH 2 CH 3 1 C 6 H 5 CH C 6 H 5 CH OH H O H CH 2 CH 3 O H H CH 2 CH 3 1 1 O H CH 2 CH 3 1 OCH 2 CH 3 1 C 6 H 5 CH HO C 6 H 5 CH OH O H CH 2 CH 3 O H H CH 2 CH 3 1 1 OCH 2 CH 3 C 6 H 5 C O 1 H H H 1 C 6 H 5 C OCH 2 CH 3 H HO Hemiacetal ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 431...
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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