Dolbier HW Solutions 363

Dolbier HW Solutions 363 - to the original carbonyl carbon....

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The molecular formula of the observed product (compound B, C 16 H 16 O 4 ) is exactly twice that of mandelaldehyde. This suggests that it might be a dimer of mandelaldehyde resulting from hemiac- etal formation between the hydroxyl group of one mandelaldehyde molecule and the carbonyl group of another. Because compound B lacks carbonyl absorption in its infrared spectrum, the cyclic structure is indicated. 17.40 ( a ) Recalling that alkanes may be prepared by hydrogenation of the appropriate alkene, a synthe- sis of the desired product becomes apparent. What is needed is to convert @ C ? O into @ C ? CH 2 ; a Wittig reaction is appropriate. The two-step procedure that was followed used a Wittig reaction to form the carbon carbon bond, then catalytic hydrogenation of the resulting alkene. ( b ) In putting together the carbon skeleton of the target molecule, a methyl group has to be added
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Unformatted text preview: to the original carbonyl carbon. The logical way to do this is by way of a Grignard reagent. 1 1. diethyl ether 2. H 3 O 1 O C 6 H 5 C Cyclopentyl phenyl ketone CH 3 OH C 6 H 5 C 1-Cyclopentyl-1-phenylethanol CH 3 MgI Methylmagnesium iodide C 6 H 5 H 3 C C CH 3 OH C 6 H 5 C 1 O C 6 H 5 C CH 3 2 THF H 2 , Pt acetic acid 1 O 5,5-Dimethylcyclononanone CH 2 5,5-Dimethyl-1-methylenecyclononane (59%) CH 3 1,1,5-Trimethylcyclononane (73%) (C 6 H 5 ) 3 P CH 2 1 2 H 3 C H 3 C H 3 C H 3 C H 3 C H 3 C ? O H 3 C H 3 C 5,5-Dimethylcyclononanone H 3 C CH 3 H H 3 C 1,1,5-Trimethylcyclononane C 6 H 5 CH CH O OH O HO CHCHC 6 H 5 C 6 H 5 CH C O H HO CHC 6 H 5 HC O OH O O C 6 H 5 C 6 H 5 OH HO Compound B ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 457...
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