spring09 140A final key

spring09 140A final key - 1f JoD T (r04 f -i. (20 pts)...

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Unformatted text preview: 1f JoD T (r04 f -i. (20 pts) (S)-monosodium glutamate, the active ingridient in MSG flavor enhancer, exhibits a specific rotation of +24. The condensed formula is shown below. Draw the Lewis strygture of MSG (need not be in 3-D) and indicate the hybridizationof the nitrogen atom and all oxygen atoms. l+ - ij-/d H Il ,'O', ( ,. | | ;' tt 'rP /Lh@ l.l--C-q-l -c-t--c-e? J tl l- | | t' icr H H H Draw the three-dimensional structure of the (S)-enantiomer of MSG (show the amino group as simply NHrl. t)rtt H H H NC! Nq $ ..tt s fUu., Lctu( /*r 49 H/:, \* rr.a- a. ^--c1^-/t\-P. ;Yfh' l, 'f ,i{, \^.* FruA L NAME:_ KT a) TH' o--l ll - r HOfiCHCH2CH2CO Na' o fo7- b) o i JO; l+ F, iD: c) If a commercial sample.of^(s)-MSG were'found to have a specific rotati ion of +12. what would be its optical purity? d) What would be the percentages of the S and R enantiomers in the mixture described above? |fz t Jr% 4 e) Is the (R)-isomer of MSG dextrorotatory or levoratatory? L+ V0A,+IalTo'Li' NAME: l-ii. (15 pts) For each of the following one-step transformations show the movement of electrons by using the standard curved-arrow notation. Show all formal charges for each structure to the left and to the rieht of the reaction iurow. ?". H-fcH3 SMe b) CN I \--^\-4",,,,,cHs ,l H *Q" d) a\ tl I CMe3 "p e) p o @oA=, 3 q?" E-df*".ji"" ?,5 (; NAME: l'iii. Qslt:)-@ shgyLo_y I9u would achieve the formatio-n of oQrtcHMecHroH from BTCHTCHM:"C^|!91I?I-?,you will need-to prote-ct the oH tun'ction- For each srep of your synthesis show all of theproduct(s). show all of theproduct(s)....
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This note was uploaded on 02/05/2011 for the course BILD 2 taught by Professor Schroeder during the Spring '08 term at UCSD.

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spring09 140A final key - 1f JoD T (r04 f -i. (20 pts)...

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