Dolbier HW Solutions 342

Dolbier HW Solutions 342 - O CH 3 CH 2 CH Propanal O CH 3...

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( c ) All the aldehydes yield chiral alcohols on reaction with methylmagnesium iodide. Thus, A stereogenic center is introduced in each case. None of the ketones yield chiral alcohols. 17.20 ( a ) Chloral is the trichloro derivative of ethanal (acetaldehyde). ( b ) Pivaldehyde has two methyl groups attached to C-2 of propanal. ( c ) Acrolein has a double bond between C-2 and C-3 of a three-carbon aldehyde. O H 2 C CHCH 2-Propenal (acrolein) O CH 3 CH 3 C CH 3 CH 2,2-Dimethylpropanal (pivaldehyde)
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Unformatted text preview: O CH 3 CH 2 CH Propanal O CH 3 CH O Cl Cl C Cl CH Trichloroethanal (chloral) Ethanal O 3-Methyl-2-butanone 1. CH 3 MgI 2. H 3 O 1 2,3-Dimethyl-2-butanol (achiral) OH O 3-Pentanone 1. CH 3 MgI 2. H 3 O 1 3-Methyl-3-pentanol (achiral) OH O 2-Pentanone 2-Methyl-2-pentanol (achiral) 1. CH 3 MgI 2. H 3 O 1 OH H OH C 4 H 9 CCH 3 O C 4 H 9 CH 1. CH 3 MgI 2. H 3 O 1 436 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP...
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