Dolbier HW Solutions 336

Dolbier HW Solutions 336 - 430 ALDEHYDES AND KETONES...

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( c ) The cyclic acetal derived from isobutyl methyl ketone and ethylene glycol bears an isobutyl group and a methyl group at C-2 of a 1,3-dioxolane ring. ( d ) Because the starting diol is 2,2-dimethyl-1,3-propanediol, the cyclic acetal is six-membered and bears two methyl substituents at C-5 in addition to isobutyl and methyl groups at C-2. 17.9 The overall reaction is The mechanism of acetal hydrolysis is the reverse of acetal formation. The f rst four steps convert the acetal to the hemiacetal. Step 1: Step 2: Step 3: 1 C 6 H 5 CH OCH 2 CH 3 1 H H O C 6 H 5 CH OCH 2 CH 3 O H H 1 1 O H CH 2 CH 3 C 6 H 5 CH OCH 2 CH 3 1 C 6 H 5 CH OCH 2 CH 3 O 1 H CH 3 CH 2 11 C 6 H 5 CH O H CH 2 CH 3 OCH 2 CH 3 OCH 2 CH 3 H 1 O H CH 2 CH 3 C 6 H 5 CH OCH 2 CH 3 O 1 H CH 3
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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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