Practice Exam #11 key

Practice Exam #11 key - Chemistry 322a f 325a-2 Name...

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Unformatted text preview: Chemistry 322a f 325a -2- Name: Practice Exam #1] 1. (6 pt) In each pair of compounds, circle the stronger acid (2 pt each). 0 o x 9 ,H N‘N’H /lL® ELGD E169 HSC—S—O \ N“ Etw—H Et‘lD-H II ® I \ I I a. o b. H H a Et Et __../" 2. (6 pt) F or the indicated hydrogen atom, estimate the water-referenced pKa (2 pt each). a. Q9 b. Br-® C. (QUE-fie 3. (6 pt) In each pair of compounds, circle the most reactive nucleophile for an 5N2 reaction (2 pt each). a_©\OH ® hHIEEag—NHz Hg—NHQE COSH 4. (6 pt) In each pair of compounds, circle the most reactive electrophile for an 8N1 reaction (2 pt each). 5. (12 pt) In each pair of compounds, circle the strongest bond, that is, the bond with the largest homolytic dissociation enthalpy (2 pt each). H-CI Cl—CI l—l C. HO—OH 0-H) Q RWH 6. (6 pt) In each pair of compounds, circle the one that will polymerize most rapidly if heated with Al'BN (2, 2’-azobisisobutyronitrile, radical conditions) (2 pt each). [mm H. "(or E innit" g hamfi ("é-cor {fl Chemistry 322a a“ 325a —3— Name: Practice Exam #11 7. (6 pt) In each pair of compounds, circle the one that is most likely to undergo a carbocation migration if treated with 1-12504 in H20 (2 pt each). «kwfik a. CH b. 8. (8 pt) Predict the K9 and AG" for this reaction using your knowledge of pKas and thermochemistry (4 pt each). I. 11;." a .1; FM. ?‘ Keq = {(3 AG” = “Li?- kcal/mol 9. (12 pt) In each pair of comp0unds (or conformers), circle the one that is more highly strained. In the event of a tie, circle both (2 pt each). Chemistry 322a ! 325a -4- Name: Practice Exam #1] 10. (50 pt) Fill in the missing starting product or reagent from the synthetic schemes below. Be sure to include any stereochemical details that you are able to describe. Although it is not important to indicate the inorganic side products, indicate all of the organic products. Where applicable, indicate whether there is a major product or if materials are formed in a 1:1 ratio (5 pt each). \ r. 03 ii. 2n, HOAc I i. Br2 (in CH20l2) ii. KOtBu g? f {A x. +AIBN, heat W ' ’/ 0A ' Ill-n0 \ + ’BuOOH, HBr. heat EtOH cat. NaOEt Chemistry 322a I 3253 —5— Name: Practice Exam #11 Mecca» Me heat 002Me 002Me Me n Poly(methylmethacrylate), pMMA, plexiglass® h. MS: 108 gfmol 11. (9 pt) Taxadiene synthase converts geranylgeranyl diphosphate to taxadiene in the biosynthesis of Taxol®, an important first line chemotherapy drug for many cancers. Ozonolysis of taxadiene (followed by treatment with zinc and acetic acid) gives trione A (below). Propose a structure for taxadiene. m taxadiene 1. further biosunthesis B NW) 0 \ —- taxadiene Z _ \ synthase 2. C13 side chain acylation ‘ . OPP Ph/QLO" ‘ H : A00 0 0H geranylgeranyf Ta off”) diphOSphare CH0 x i. 03 ii. Zn, HOAC [.1 v4 ‘/\ H 3“ labia/LN or Lit-CR Chemistry 322a K 325a —6— Name: Practice Exam #1 l 12. (10 pt) Write a reasonable curved-arrow mechanism for the reaction below. Show each bond- forming and bond-breaking step distinctly. Both starting materlal and product are single enantiomers. ...
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This note was uploaded on 03/04/2010 for the course CHEM 322AL at USC.

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Practice Exam #11 key - Chemistry 322a f 325a-2 Name...

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