Ans Exam2 B - 8L 2 Beau. Ant. Part I. (60 pt) Choose a...

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Unformatted text preview: 8L 2 Beau. Ant. Part I. (60 pt) Choose a single best answer, and write your choice on the cover page. 1. (5 pt) Which reaction in each of the following pairs will take place faster? Circle it. DMF f >L/Ci :+ CH3Sef --—-—--D-' CH3 + Cl' l y‘r Lac-LL ‘\ ____ 'Mu Ala." b e DMF ' CI + CH3O ""—""* CH3 + Cl‘ {L Ron + CH3$ SCH3 + Cl‘ L ( 3'” Z) c >L/ e ; DME’ c. 0+ CH3S SCI-13 + (21* l a. CH3Br + H0' fl... CH30H + Br‘ 0 CH3Br + H0' —-—————'—* CH3OH + Br‘ {H20 is both a solvent and a reagent] 0 + H20 -—-- >—0H + H1 M (0'. 2mm?- CH3CHCH2B1' + CH3OH —I-— CH3CHCH20CH3 I a. I CH3 J_./"'”“ W, CH3 [Solvent in both case is alcohol] CH3CHCH2Br +{I;EH30@; —-. craggrrcnzocn3 i CH3 b, Mu CH3 2. Which of the following (A-D) may serve as a starting material to synthesize the alkene product? A B Cl C D 1 f ' a; 0—}; [>4 EMA Oév E. AandB @Aandl) 4:2:5 O=< 3. What is the starting material in the reaction below? + CH, H OH— A. CH, H s. CH3 CH3 s. CH3 H (DH, 5r Hl Hl Hi H1 I | HI Hi H Br H OH . . . . . . _ _ z emit 4. Which of the following alkyl bags reacts fastest in an E2 elimination reaction? A. s. n. E. CH3 CH2}: CH3 CH3 CH3 0/ O“ 0* (I Br I 5. Consider the following reaction. Assuming no other changes, what would happen to the rate of the reaction if the concentrations of both the alkyl halide and the OH' were doubled? CHacHZCHZCHgBr + OH‘ —> CH3CHZCHZCH20H + Br' A. No effect B. The rate would double. C. The rate would triple. The rate would increase 4-fold. . The rate would increase 6-fold. 6. Which of the following anions is the best leaving group? A. NH;' Cl' C. CH3' D. OH‘ E. H“ 7. What is the missing reagent in the reaction below? ‘_ TsCl SOC12 9'13 - ?H3 D. FBI; ch—(f—CHz—OH ——-————-——+ Hsc—-CH—CH2——CI E HI H 8. Which of the labeled protons (PL, Hb. . . )in the following compound is most readily abstracted under conditions of E2 elimination? He OHS [32:13 A. Ha B- Hb ch Hd E. He HaHb Br He 9. How many dehydration products would be possible in the reaction below. CEOH H2804 A.0 3.1 (3.2 @3 E4 10. Which of the following alcohols cannot be dehydrated? *0”°“‘CE.°O<°HOO” (I... l 1. Which of the following has the Z-configuration? MSQHC CH H02C CH CH HO CH CH H N CH NO jc=cz 3 )c=c: 2 3 )c=c: 2 3 2 jc=c§ 2 2 H OH Hon-120 CH3 HOHZC CH=CH2 H3O cm A C D 12. Predict the product(s) in the reaction below. $1.: + m" m m. (I. 0’ c- Q 0’ a (I... :6"on ‘wnpn OH 'Wzoa ’CM‘W’ 13. Determine the product(s) in the reaction below. rcHS (>3 :1: 'CN '- 9] “2° 0 H o A: 9.. . =9 H. A. c. o. anemic IIICN "(GM ON CN 14. Determine the product(s) in the reaction below. +HCI —l'~ OH "-01-: 0. (9 c: B- c. D. A. and c E. B and c 15. Give the IUPAC name for the following compound. H A. 3-ethyl—2—methyl-4-heptanol B. 4—ethyl-6-methyl-S-heptanol 4-ethyl-2-methyl-3—octanol E 4-ethyl-2—methyl—3-heptanol None of the choices are correct. 16. Give the IUPAC name for the following compound. A. (Z)-2,3,6-trimethyl-2-heptene CH3 H2°H<CH202 B. (Z)—2,3,6—uimethy1~3-heptene E)-2,3,6-trimethyl-3-heptene CHacH H D. (E)-2,3 ,6-trimethyl-2-heptene EH3 E. (E)-2,4,6-tnmethyl—3-heptene 1r" .(2 a. 17. Which of the following reactions is an example of Markovnikov‘s rule? ; N d‘” A CchHZCH =CH2 CH3CH20HZCH2 C] We CHgCHz —CH :c —CH3 —- CHacHQCHz-C —c: J3”. 33H. 0. CH30H2 -—CH=C -—-CH3 ————-—- CchHZCHCH(CH3)2 l 1 CH3 c: 18. Rank the following compounds from least to most stable. 3— t b. I c. l m m 19. Predict the major product. 0% Brzfizo ? Ol/‘m OV‘Br O/‘OH O/‘OH 20. Predict the product(s). 1. 3H3 1r Tr( (9H CH 0“ O Q“ q?“ A. B. C. D. v’ v“ @A and B F. C and D 21. Predict the product(s) of the reaction: 11+, H20 0H B. C. D. 0 —»? O’ 0: fi 22. From the list of possible carbocations, which one is least likely to rearrange? A- (f3: 3' ffla @ CH: 9' tlma 5‘ on. CH3CHCHCH3 CflséHgiCl-ls CHJ: when3 CH3CHCH2 CH3rl25HCH,CH3 ‘ - 1 CH3 cu, 23. Predict the product(s). H: (1 H8: H: A- O; B. O: c. (1/ D. @ande F.CandD E l- . h ‘/ ' V Br 3, Br 24. What is the starting material in the reaction below? HBr (excess) —-—-—-——--—--— Br (only product observed) 25. Give the IUPAC name for the following compound. A. 4,4-dimethy1-2-hexyne 2 ® 5,5—dimethyl—2—hexyne CH3C "— CCH2C(CH3)3 C. 2,2mdimethyl-4—hexyne 26. Determine the product. 0 H36 : — 2 g \CH2 1) FIG—C H 2) Hp @ CH 3' HC c' if H0 G/// \\C CH T 0 A74 H Hp: f \ H10 H H H H’c H H H CH 27. Which method would work the best in carrying out A. (I) HBT; (2) 2 NaNHZ the following conversmn? CE (I) BE; (2) excess NaNH2 ? C. (1)1313, H20; (2) warm2 caHa-CH=CH-CEH5 ' CeHs—CEc—CEHE. D. (1) 3H3, TI-IF; (2) H202, NaOH; (3) NaNH; E. (1) NM; 28. What is the IUPAC name for the following compound? @— @ 4-mefl1ylcyclohexene . 5—methylcyclohexene C. 1-methy1-4-cyclohexene D. 1-methy1-3-cyclohexene Part II. (20 pt) Fill in the boxes. Show stereochemjstry where necessary. I N" 0H /\/ 0 7‘ NaBr TsCl ———-s- g pyridine U DMSO I pt" .. __..— h— ;rr Cit-(30‘ (NJ) Part III. 1. (10 pt) You have ethyl bromide, acetylene, ethylene oxide, and any other inorganic chemicals to prepare several compounds shown in the following scheme. Show your syntheses by giving the correct reagents (and the intermediate compound, as indicated) in the boxes. HCECCH2CH20H CH3CH2CH2CH=0 CH3CH2-C-CH3 2. (4 pt) Suggest a synthesis of cyclohexene oxide from cyclohexene. You can do it directly or by a two-step process. 0 5}} {fax 1: H10 It. 0 Xx I..- 2r!" _} L‘HHns...» — w—u-«Far‘def .... .. . _ _ , {Qt/II“) 3. (6 pt) Draw an enol or keto structure for the following. Ifthere cannot beasuch a structure, write "X". to OH Ai H—W 5‘" M 21%- WOH W 0 5’ In!" MOH Bonus questions (8 points): Propose a reaction mechanism to account for the formation of the observed product. You must draw the structures of the intermediates correctly HO CH3 CH3 112504 i, C 3 £& + A H Ni CH; C”: _.. i- ') G) _'_ ‘ L“.— Me A L wan-“9 i O 4" CL" Jib-F (9 n ...
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Ans Exam2 B - 8L 2 Beau. Ant. Part I. (60 pt) Choose a...

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