{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

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

Info icon This preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
Image of page 7

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 8
This is the end of the preview. Sign up to access the rest of the document.

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) ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern