final%20exam%20grading%20key%2008Dec18 - Name ~_8 Fa1l200B...

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Unformatted text preview: Name ~_8(------- Fa1l200B, 4:122 Final Exam 1) Draw the indicated structures and reagents. No mechanisms. [3 pts each box) a) Two different combinations of Wittig reagent and carbonyl that give the alkene at nght. Show EACH Wittig and carbonvl pair in a separate box. o \-1[\\ ~_" \::::.T ew t- 6'\d b) Two different alkylation reactions that give the product at right. Start with two different enolates. . ~ OQ- \)~A1~ 7)~\<;,Ot- G{,ts rt~ ~.~ I ~ ~~ F;~ ~~S \ ~ Ctts CNt~ _\ ~M)3. ~ ~}) ~~l ~ ,- ~~~Lt , ~ l ~~ G(,.t~ ~ 1h ~p ~ \ 1 ~ a;tJz.- 1'L4 -0 -- A H2NCH2C02CH2CH=CHCH3 CH 3 0 CCH CH=CHCH C",N Name_ke---+-~ __ Fall 2008 4-122 page 2 of 8 2) Select all choices that apply. One or more answers are possible for each, [4 pts; # correct - # incorrect) fl ,8i (:=0 a) Select the structure(s) consistent with these spectrocopy data: strong stretch between 1780- 1680 cm' ; broad peak(s) be.tween 3~OO-3400 cm- 1 ; no peaks 2200-2300 cm- 1 ; multiple peaks.2800-3D,OO cm- 1 . {?\.\ '-..>Yt ~ 0 V"rH.$ ($0 S 3 0-"t" CH OCH 2 C",CCH 2 CHO 3-bromo-4-phenylpentanoic acid 3-methy\-4-pen n-2-ol HOCH 2 C",CCH 2 CH OH -p~\r"&"'---- b) Which of the structures have a H-NMR that contains a doublet from spin-spin splitting. o II CHJOCH:zCOCH2CH3 a CH3 Cl I I I CH~-CH -CQ-I J I I H H a 0 I I II r CH~H2COCH(Q-IJh I a E r+ ) t:" c) Which of the structures have a H-NM that has an integration of 3H : 2H : 2H : 3H ?...
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This note was uploaded on 02/16/2010 for the course CHEM 122 taught by Professor Pienta during the Spring '08 term at University of Iowa.

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final%20exam%20grading%20key%2008Dec18 - Name ~_8 Fa1l200B...

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