Dolbier HW Solutions 358

Dolbier HW Solutions 358 - 2 CH 2 OH CH 3 COOH Ethylene...

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The order of decreasing sequence rule precedence is HO . CN . C 6 H 5 . H. The groups are arranged in a clockwise orientation in order of decreasing precedence in the R enantiomer. 17.36 ( a ) The target molecule is the diethyl acetal of acetaldehyde (ethanal). Acetaldehyde may be prepared by oxidation of ethanol. Reaction with ethanol in the presence of hydrogen chloride yields the desired acetal. ( b ) In this case the target molecule is a cyclic acetal of acetaldehyde. Acetaldehyde has been prepared in part ( a ). Recalling that vicinal diols are available from the hydroxylation of alkenes, 1,2-ethanediol may be prepared by the sequence Hydrolysis of ethylene oxide is also reasonable. HOCH
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Unformatted text preview: 2 CH 2 OH CH 3 COOH Ethylene Ethylene oxide 1,2-Ethanediol H 2 C CH 2 H 2 C CH 2 H 2 O HO 2 O O CH 3 CH 2 OH Ethanol HOCH 2 CH 2 OH 1,2-Ethanediol H 2 C CH 2 Ethylene H 2 SO 4 heat OsO 4 , (CH 3 ) 3 COOH (CH 3 ) 3 COH, HO 2 2-Methyl-1,3-dioxolane HOCH 2 CH 2 OH and CH 3 CH O O O H CH 3 CH 3 CH(OCH 2 CH 3 ) 2 Acetaldehyde diethyl acetal 1 CH 3 CH O Acetaldehyde 2CH 3 CH 2 OH Ethanol HCl CH 3 CH 2 OH Ethanol CH 3 CH O Acetaldehyde PCC CH 2 Cl 2 CH 3 CH O and CH 3 CH 2 OH CH 3 CH(OCH 2 CH 3 ) 2 Acetaldehyde diethyl acetal ( R )-Benzaldehyde cyanohydrin C 6 H 5 H OH CN C 452 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP...
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