practice-11-key

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

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Unformatted text preview: Chemistry 322a f 325a -2- Practice Exam #1 l 2. For the indicated hydrogen atom, estimate the water-referenced pKa (3 pt each). 2 H (mg; 3109 we aim {1-H rig) is 13 .— fli— mm“? s 3. In each pair of compounds, circle the most reactive nucleophile for an 8N2 reaction (3 pt each). . R: ms, - a. "'3G H II o W o o6: a, OH NH,» . hsc b, C. 3H 3 s j; V' b 4. In each pair of compounds, circle the most reactive electrophile for an 5N1 reaction (3 pt each). 5. In each pair of compounds, circle the strongest bond, that is, the bond with the largest homolytic dissociation enthalpy (3 pt each). flit—E} CI-C| b. @ "' C- “0—0” @936} Hate—SH e.@ H3C_| AIBN (2,2'-azobisisobutyronitrile, radical conditions) (3 pt each). \ H _ H {H " _ HX : CH O/\ b. HHH a H 3 Mm,” 7. In each pair of compounds, circle the one that is most likely to undergo a carbocation migration if treated with I-IZSO,i in H20 (3 pt each). OH HO I My“?! f“ at“; AX % 'HO>_<OI-li[§ HOH OH _ f a. b. c. an Chemistry 322a! 325a -3- Name: Practice Exam #1] 8. Predict the Kenl and AG" for this reaction using your knowledge of pKas and thermochemistry (4 pt each). v 955%»; F53 “9 d” h H— ' I u _ - . {[1 cc. ( \\ * S- - "" g 5 : if) / ' g Keq = 50 '57 AG" = - '1 ital/hat" ~- 9. Propose a plausible mechanism that accounts for the formation of a mixture of compounds B, C, and D when compound A is treated with HBr. Ignore stereoisomers for simplicity (12 pt). ; I- 3- Br :5 I :5- I — g Brg Br 3.1 if —"' + + 1: j “I; { II T T 1'...” B c D t a.” —- "cf; A _ (both enantiomers form) (all4stereoisomersform) h. w“ t/ if»: a;fl__ ,)- r- ‘ i Q / M, 3 ~... "' Fr 1 A" v I I ." 'J 4 ” d 1 E q. ‘ I N a ' a. 5‘ y" g J § ‘9' ) "' :3" _' '- 1'" If _ _ .. _, f " _-" ,.,. ‘ . I Jh “it: .5 g i {a g- L v {my} Ill-4}.) .m «' 1 ~ ' ‘- -<,_'m. Chemistry 322a I 325a -4— Name: Practice Exam #1 1 10. 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). 1‘ Br2 in H20 i.O3 iLZn,HOAc W + AIBN, heat [::T/** + BuOOH,HBn heat LBHyTHF H.H202,HaOH /fl// + Bs(nmcHzcs) b. c. d. e. Chemistry 3223 l 3253 -5- Name: Practice Exam #1 I Br ;"‘-"é-'_L. risin- v ,,.., —~ 3 MC; pests-~.“¢s(st:_ + 1 )g‘ I {7 to ~'\./ —" CI CI l a, C .2 +9, 5 3 Gaga [a '3, a] Egg—{k \ “a: 11. Limonene is a natural product isolated from pine trees. It has the empirical formnla CmI-Ilé. a Limonene decolorizes bromine in CHZCIz, and when hydrogenated over palladium on carbon, it gives a product of formula CIOHZD. Ozonolysis of lirnonene (followed by treatment with zinc and acetic acid) gives the compound below, plus a 1-carbon piece. Propose a structure for lemonine (10 pt). i' 03 W0 ii. Zn, HOAG O H Chemistry 3221} 3253 Name: Practice Exam #1 l -6- 12. Propose a synthesis of the compound below from the indicated starting materials and any reagent that you think is appropriate (20 pt). 5‘ ‘ 3 met: ; 33* ‘7 a g n | 1' “1'5! 4i) f")? é KO“ f "it I [42- o we M J “‘ xv“ :" I (gr 5'. i ‘4 I‘ P" ‘3'; h f 3 'i // K“ r: a . 2 ,fl‘“ K N I. L”? Hm I; __ " j" H...“ 'x ” ' 3, i.» .41 1" If: ' ’ *' {Vt L _ P , . a 212 “Uh-L; ’— _,:+- “I. I:- "' Jr is} :3 J on r , ...
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practice-11-key - Chemistry 322a f 325a -2- Practice Exam...

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