322bf04_final_key

322bf04_final_key - Organic Chemistry 322 bL Fail 2004...

Info icon This preview shows pages 1–18. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

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

View Full Document Right Arrow Icon
Image of page 8
Image of page 9

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

View Full Document Right Arrow Icon
Image of page 10
Image of page 11

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

View Full Document Right Arrow Icon
Image of page 12
Image of page 13

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

View Full Document Right Arrow Icon
Image of page 14
Image of page 15

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

View Full Document Right Arrow Icon
Image of page 16
Image of page 17

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

View Full Document Right Arrow Icon
Image of page 18
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Organic Chemistry 322 bL Fail 2004 Final Exam, December, 13, 2004 Initial of Last Name fl - T.A.’s Name ) Name 1. (60 pts) 2. (6 pts) 3. (12 pts) 4. (1 0 pts) 5. (15 NS) 6. (10 NS) 7. (8 NS) 8. (6 NS) 9. (8 pts) 10. (10 pts) 11. (8 pts) 12. (8 pts) 13. (8 pts) 14. (10 pts) 15. (8 pts) 16. (8 pts) 17. (5 ptS) 1 each 1. Write the products of 30 of the following 31 reacfions. You must clearly indicate the question to which you are not submitting an answer. Put the letter (N). (60 pts.) fi’ 0 C e e. CE \0 HCI / NaNo2 _.__——_.> NH2 / QM 1 cat NaOEt o. CH2(COZEt)2 + /\CN ———’ EtOH 1:355 $04 ‘ \COLQC' + PhMgBr $73? W“ CWJCEH ’ 3 0H X. + CH3- CH2- -Li C \/ then hydrolyze o u H Ph-C-CH3 + Ph-NH-NHZ ———°a—t§—'V—S'S—-> ?L\’C\CM3 O CH’QY) .‘“ 3 \ / Ph‘C’CH3 + CFs‘l‘E‘OOH _ OCH3 i O y O NH:(liq)/EtOH 0/ (Mb #6 wag-7% ' 4 % CYC oh{%‘M (P O z QEKH + CH3EPh base Wflh CS-J‘QM’I. O ' unflcc) 6‘31? Vi aa 6 |_[)A B be 0/” [\/( Q C) dd. EtO-E—(CH2>—E-0Et NggEt O 4 dil. H30e . W3 6/ H o ee. Et02-C-C-CO2Et _H___2_, 0K3 £%{:> A WR/CQH C2 Draw the structure of' Isoprene and circle the isoprene units in geraniol. I(8’ pts. ) \fi} V/ geraniol 3. Outline mechanistic steps which account for this sequence of reactions. (12 pts.) 4% CN iii 9% ”—1 mtg—way? CE” lune». each-11M i w/PARLjAE—fi 4. The coupling of an aryl diazonium salt with phenol to yield an azo compound occurs best under mildly basic conditions. Show with chemical equations and some narrative, less than 30 words total, why strongly basic or acidic conditions are less favorable. (10 pts) ' 5. C. Give an example of the use of five of the following ten reagents. (15 pts.) a-(>/>\AIH DIBAL ./C;O,DQ< p... O @réfi‘k’“ O Q 9 (’3 (CH3)2CULI / £ / %\@> PA—Cuo we h. Rani/+438 C,\62vt/$ Ml’éjcok . ‘ (11/ 02"\/\70\A/0><7 WJCWWQI‘MfidflS (‘3 ‘- KEN-Br NBS g g + film 0 6. Write the product of the following reaction. Assume the reaction went only 90%. Use chemical reactions to show how you could purify the product using a separatory funnel and suitable reagent solution(s). (10 pts.) 1) HCl/ NaNo2 OH NH 2 2) CugO, CuO )1“; ca H20 CH3 /"*\ l ' . What' Is the structural difference betw een cellulose and amylose? Both are polymers of D- glucose; Write structures to show the differences. QvaIl kMDCM/‘W O CLO/0AM W, (ow mlE<®QUVEEWWXKM (xvii-vi: “l ”0 II0 7W" ("6' (W) 06(3wa W H 8. 9. The n—molecular orbital of a 1-3-butadiene are drawn below.‘ Label these bonding (B), anti-bonding (AB) or non-bonding (NB) as appropriate. (6 pts.) Specify conditions to remove the protecting group from the species drawn below. Write the structures of the products formed from the protecting groups after their removal. (8 pts.) 0 . CHanog-N-H $H-E—NHWM (20 AW 7 O of?) l? l’ 'L Ph-CHz-O-C-NH-fH-C-NH W H. mm Ll ’ » ._.____» Firms .‘7/ 12 10. Draw chair structures for the A, B and C rings of cholic acid. Label the substituents axial or equatorial as appropriate. (10 pts.) 4 % A} a F3 F3 HNo3 —> H2804 NO 2 In no more than two sentences account for the difierent directive effects of the CH3 versus the CF3 groups in the above reactions. (8 pts.) 13 ,12. 5H3 . . - . . . . CaffeIne Is found In coffee and tea. It Is a purIne)as Is _ ITI:3 H </N I N/ G ' H In the presence of ribose, guanine reacts to form guanosine. Write a mechanism for this reaction. Why (/N I does caffeine not react with ribose to form Nil-'2 caffeinosine? (8 p(t.s) . HOHZWVN , I . 0 6 fl . Guanosine \ HO OH _ \ t3“ M€CL Home) ’ ‘ $ANV‘7) \4 MOW/(L (9 H9 0 ® ~ on -»~ m HO on D MD ME) t0 2W \ < , NO 13. + HNOa 2 st04 Write the structure of the electrophile in this reaction. Write a balanced equation to show how this electrophile is formed. (8 pts.) H H? O’ 14. Arginine is the most basic amino acid. H2N-E-NH CH2'CH2'CH2' _ 02H V «’9‘ 2— H It has three pKa's: 2.2; 9.0; and 12.5. 1% k Assign these to the appropriate functional group . Write resonance structures for the group whose pKa is 12.5. (10 pts.) 15 O 15. The bond lengths of 0-0 bonds in benzene are all the same, 1.39 A, whereas those in _ o o cyclooctatetraene alternate between1.32 A an 1.46 A - Account for this difference in no more that two sentences. (8 pts.) fie Et 9 0H9 ll , - 16. Write the product of the reaction CH3Hh3—C—Ph _—’ C442.” Q)” Q’ ?L‘ if Bra (él/ (anaemic, M < 7/0 two i! 3‘ If bromine is replaced by iodine, the reaction rate is the same. In explain why. (8 pts') ' " (A McCain. wig/3 , ' 974m 5’ 156% \l‘e/lcxelfihG 0 W0“; _ A ‘ Aegco/mMin sxcu‘) * . q’ W, o «mitten occwvs 133”" “:36" A ‘ . whim-'5» \ ‘ 0Q 0m0\a>ct V“ ‘9 ”\fl/ Aéfl L H) 17. How does retinal become chemically bound to the protein opsin to form Rhodopsin? (5 pts.) \\—- 1 1-cis-retinal 17 ...
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