Dolbier HW Solutions 382

Dolbier HW Solutions 382 - Lithium dimethylcuprate...

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18.16 The enolate of dibenzyl ketone adds to methyl vinyl ketone in the conjugate addition step. via The intramolecular aldol condensation that gives the observed product is 18.17 A second solution to the synthesis of 4-methyl-2-octanone by conjugate addition of a lithium dialkylcuprate reagent to an a , b -unsaturated ketone is revealed by the disconnection shown: According to this disconnection, the methyl group is derived from lithium dimethylcuprate. 18.18 ( a ) In addition to the double bond of the carbonyl group, there must be a double bond elsewhere in the molecule in order to satisfy the molecular formula C 4 H 6 O (the problem states that the CH 3 CH 2 CH 2 CH 2 CH CHCCH 3 O O CH 3 CH 2 CH 2 CH 2 CHCH 2 CCH 3 1 LiCu(CH 3 ) 2 3-Octen-2-one
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Unformatted text preview: Lithium dimethylcuprate 4-Methyl-2-octanone CH 3 CH 3 CH 2 CH 2 CH 2 CH CHCCH 3 O O CH 3 CH 2 CH 2 CH 2 CHCH 2 CCH 3 Disconnect this bond. CH 3 CH 3 b a 2 1,3-Diphenyl-2,6-heptanedione C C 6 H 5 CH 2 CHC 6 H 5 O O CH 2 CH 2 CH 3 C H 3 C C 6 H 5 C CHC 6 H 5 C O HO CH 2 CH 2 CH 3-Methyl-2,6-diphenyl-2-cyclohexen-1-one NaOCH 3 CH 3 OH 2 H 2 O C 6 H 5 C 6 H 5 O H 3 C C 6 H 5 CH 2 CCHC 6 H 5 H 2 C O O 2 CHCCH 3 C 6 H 5 CH 2 CCHC 6 H 5 2 O H 2 C O CHCCH 3 Methyl vinyl ketone 1,3-Diphenyl-2,6-heptanedione Dibenzyl ketone NaOCH 3 CH 3 OH C 6 H 5 CH 2 CCH 2 C 6 H 5 1 CHCCH 3 H 2 C O O C 6 H 5 CH 2 CCHC 6 H 5 CH 2 CH 2 CCH 3 O O 476 ENOLS AND ENOLATES...
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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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