Exam 3 (key) - Name: . Exam 3 Chemistry 333 (Fall 2010)...

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Unformatted text preview: Name: . Exam 3 Chemistry 333 (Fall 2010) Question 1 28 points ' Question 2 26 points Question 3 ' I 13 points Question 4 15' points Question 5 18 points Extra Credit 5 points Total 100 points [atoms aith I lith i flirt. 1:5 IEPM flue-He I “Cum-PI: ...-..: "ti-tr. flsbarne, are? I be fumed? '"Just for the retort], Gerkins, in the absence of My brain I5 full- getting actual molecular bonds to form oust tape is not an option.” Chemistry 333 . I Exam 3 Fall 2010 1) ' Fill in the blanks. Where appropriate show stereochemiatry and stereoisomers. (Note: some transformations may involve more than one reaction). ' . I 1)BH3 AA *—' 2) HOOH NaOH A) Br only product 3) alkene 0” 1) H3PO4 (strong acid) ______________._____... CH3 2) HBr 0) )Y 1) TSCI, pyrdine —_._ OH 2) NaCN D) Chemistry 333- Exam 3 Fall 2010 1 equiv. HBr _ “ec/ __—'_'—__"" / >—<' \ Br E) 1) 03 _ |= ' —-—-- ) 2) M328 9 €53 - Williamson ether I ' New. ,3er synthesis (SK/D a + G) Brim __ _ OH H) I ' IUPAC name Chemistry 333- Exam 3 Fall 2010 2) Draw the mechanisms for the following reactions. You need only draw one termination steps (Again show all arrows to get full credit.) >= HBI' Br I Fl-O-O H a) light Tuth-kwm ' 32" R a are. EDI—ha f (ffif‘ D‘fipm laflafljklj’fér —-'—"I’ K’D’H ' Br . pm ("Edd-CH1 . r" " f“),- - a {urns rim-ff: 9"" MIKE I” We, >’_ #31 (fl/[P'pr . r Wife-J >5 ml’fir #‘5” @r’ U H TUMhL-I-‘fl. 5"‘1 W Chemistry 333 Exam 3 Fall 2010 (mechanism continued) 0H CH3 Brg, H20 :3" CH the mechanism ——————5—- 3 should also explain Br the observed stre ' b“ Akita-(D m s1“me 6 1+3 (-3 “3 I 5/3, HID mes «as? 9s we ' iErr-B r" _ r- LJI (Bra) “fill‘m- pH- ; W3 L :- CH-j’ Hr’gf C...er WEN” I 3) a) Which of the following radicals is the most stable? D , - A B C D E b)'Which of the above radicals is the least stable? E . c) Draw ALL possible products of this radical bromination reaction. Circle the major product. (Do not show the same product more than once) :8( 55¢” (- I Chemistry 333 . Exam 3 Fall 2010 d) Which of the following carbocations will undergo a 1,2—shift and rearrange? (circle all that apply): M©Q§ U 4) Multiple Choice: CALVIN! ill-till Mill-2 ‘m name to we CDFFE TABLE E? ._._.r J a) A key intermediate in the reaction of (Z)-3-hexene with H2 and catalytic Pd metal is a: (circle only one) A) carbocation B) radical . A’Af/HL C) three-membered bridged intermediate If i ///////x I iye-membered cyclic intermediate é,- ne of the above B) radical C) three—membered bridged intermediate D) five-membered cyclic intermediate E) none of the above c) A key intermediate in the reaction of (E)-3-hexene with 03 followed by M923 is a: (circle only one) A) carbocation B) radical . three—membered bridged intermediate ' a, e-membered bridge intermediate E) none of the above Chemistry 333 Exam 3 Fall 2010 D include a pair of diastereomers “'3,- ‘5’ clude a pair of enantiomers F) include a pair of censtitutional isomers e) The product of the reaction of 2-butyne with H2 and Lindlar’s catalyst and the product of the reaction of 2-butyne with Na, NH3 will be: (circle all that aPP'Y)i A) both be chiral B) both be meso' \K— ism/.4 \v:_/ __ meso ' I \ 6, pair of diastereomers E) a pair of enantiomers F) a pair of constitutidnal isomers 5) Provide a synthetic routes for two of the three transformations. Write “Do not grade” on the problem that you are skipping. These transformations should take more than one step. To get full credit, draw all reagents. a) I multiple steps . Er?) CC * H—BP r N? cacti—ls H3 -—-..__—-;p fl \ FM (Sm) [QM —:—- b) mumple Step5 trans two extra carbons _...—-. NIH NH; 9 Q <_>—c:_; c. ——H -———3. a Na ___.,7 (3N2; Chemistry 333 Exam 3 Fall 2010 synthesis continued: [ I “‘le ________ -_ “LS/EM H - I multiple steps 0/ /-/:;.i MWlbfl C). K79 'tBM W H» 'PBCS (' W“ F; . gr.- NHLDET' d x3 052) Extra Credit (On the board) ...
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This note was uploaded on 03/05/2012 for the course CHEM 333 taught by Professor Lavigne during the Fall '09 term at South Carolina.

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Exam 3 (key) - Name: . Exam 3 Chemistry 333 (Fall 2010)...

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