Solutions_Manual_for_Organic_Chemistry_6th_Ed 95

Solutions_Manual_for_Organic_Chemistry_6th_Ed 95 - 5 - 1 8...

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Unformatted text preview: 5 - 1 8 continued mirror ( d) H H + + CHO OH OH HO HO CH20H + + CHO H H 1 80 0 rotation of the right structure does not give left structure; no plane of symmetry : c hiral--enantiomers (e) H H (f) Ho H (a) R ( b) no chiral center (c) no chiral center 5 - 1 9 If the Fischer projection is drawn correctly, the most oxidi zed c arbon w i l l be at the top; thi s is the carbon with the greatest number of bonds to oxygen . Then the numbering goes from the top down. (d) 2 R, 3R ( e) 2 S, 3R ( numbering down) i: i� CH20H C H20H OH H n 1 80 0 rotation of the right structure gi ves same structure as HO - - - - - - - - - - - - - - - - - - - on the left; also has p l ane of s y mmetry : s ame structure H HO CH20H $ + CH20H CH20H H HO OH +�: H CH20H 1 80 0 rotation of the right structure does not gi ve left structure; no plane of symmetry : c hiral--enantiomers (f) 2 R, 3R (g) R ( h) S ( i) S 5 -20 ( a) enantiomers--confi gurations at both asymmetri c carbons inverted ( b) diastereomers--confi guration at only one asymmetric c arbon inverted (c) diastereomers--con fi guration at only one asymmetric c arbon inverted (the left c arbon) (d) constitutional i somers-C=C shifted position (e) enantiomers--c h iral , mirror i mages (f) d iastereomers--configuration at only one asymmetri c carbon inverted (the top one) (g) enanti omers--confi guration at all asymmetric carbons inverted (h) same compound-superimposable mirror images (hard question ! use a mode l ) (i) diastereomers--c onfiguration a t o n l y one chirali ty center (the nitrogen) inverted 5 -2 1 (a) ' -' :; u C H3 meso structure not optical l y active l �: CH 3 " CI ' U plane of s y mmetry H 3C , l -f , H : B * � r Cl , ' , * C H3 plane of symmetry 88 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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