Exam_2_White_Key - KEY u CEM251/Fall 2010/Second Hourly...

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Unformatted text preview: KEY u. CEM251/Fall 2010/Second Hourly Exam ....... (page 1) w la t t e. (20 points total) 1. Draw the structure of the following compounds: 0H a) 2—meth I-2-butanol I. HwCJ-l. C.“ 2 pts' y CH3 C} 1 3 \. b) isopropyl alcohol “CF—.6314 2 Ms. C) 3-phehylcyclopentanol d) 2-ethoxybutane e) diethyl ether 1‘) (Z)-2-pentene 9) ' (E)-3-bromo-2-hexene h) isobutylene i) 2—phenyloxirane J) 1-pentyne CEM251/Fall 2010/Second Hourly Exam.......(page 2) (20 points total) 2. Draw the structure of the major substitution productis) of the following reactions. Show stereochemistry carefully. a) 2 pts. ‘\“‘Br N H‘C H 3 CH3NH2 ———> (3N2) CH3 2 pts. cnacnon _> .(SN1) CEM251/Fall 2010/Second Hourly Exam ....... (page 3) (10 points total) 3. Draw the structure of the major elimination groduct of the following reactions. a) 2 pts. CHZCHa 1) sou2 m1CJi3 , (swz) U ""o H 2) A: KOH ('52) b) 2 pts 0:0H20H3 -1) SOCl2 d ‘5'“ LL“ 3 '—’ (3N2) / OH 2) A, KOH (E2) ' 2 ptS. C ) \“..CH3 A Oak 3 —. i QCHS H2804 7 CC qt 3 OH (E1) CH \3 Zc/CH3 CHQ‘CZC/Q‘ H/ V H/ \CH3 . A B 4. Which one of the above configurational isomers (A or B) will be the major elimination product of the following sequences: 1) SOCI2 2pm- / (8N2) 2) A, KOH ' (E2) HO f" CH3 Hlunll CH3 H \ 1) [email protected]—SOCI2 2 pts. 2) A, KOH (E2) CEM251/Fall 2010/Second Hourly Exam ....... (page 4) (12 points total) 5. CH3 \ A) CHSCHzBT + CH—ONa —> / CH3 I CH3 \ B) CH—Br + CH3CH20Na —> / CH5 Which one of the above reactions(A or B) (2 918-) will give the higher yield of ethyl isopropyl ether? ' 6. . CHZCH3 CH20H2 CHQCHS (+) X Y 2 H 3) Which of the above carbocations (X, Y or Z) -(2 pts') 'is most stable? b) Which of the above (X, Y or Y) is a 1° Y (2 PIS-l carbocation? 7. The following reaction occurs by an E1 mechanism. Draw appropriate structures in the boxes. (2 pts.) (2 DIS.) w. 3 CH3 H20 ' Ur) 1,2 Hydride , —_—- shift initial carbocation more stable rearranged carbocation ' I (2 ms.) 0% 3 ._1 Major E1 product (22 points total) CEM251/Fall 2010/Second Hourly Exam...... 8. Draw the structure of the major organic product: a) f) h) - Cfimfij _. Gator, H\ gm C=CH2 H20 ‘ -——-> H2304 OH\3 /H Cl 0:0 —2—> / \ H20 CH3 CHQCH3 1) BH3 .__—> 2) NaOH, H202 ——F Br2 —h- excess CHzcECH 2pts. UCHcha HCI —D carbocaiion intermediate 53H 2pts. H20 ' CH CH CECH ——> 3 2 Hgso4 H9804 enol: 0H 1. CL _-C,k+ :CH 2'9ts CHZCECH 1) 3H3 r' f 41 . —. —...._ H202 enol 2 pts. Li major product ? CHJC-Harc': CH1.- —> Cl+3cfi1'C.—c-H3 major product major product .(page 5) 2 pts. 2 pts. 2 pts. CEM251/Fall 2010/Second Hourly Exam ....... (page 6) (12 points total) 9. Draw the structure of the major organic product: a) . :1: 2pts. 2pts. CHgoCI-is' @ —~f: @‘w‘t + airs-Y (excess) b) O 2 pts. /CH3 ' CH30H20H CH2 C\ H2804 CH3 0) O 2 pts. / \ NaOCH3 ————D- @CH CH2 CH30H d) Cl 2 pts. ' | CHSCH cfi-C‘“ l A C} ———> NaNH2 (excess) Elimination Product 10. Compound X' has the molecular formula C10H1sBr20. X has exactly one ring. How many at bonds are present in the structure of X? -2 pts- CEM251/Fall 2010/Second Hourly Exam ....... (page 7) (4.points total) 0 R H 11- (2 DtS-) Nitrosyl chloride (N—Cl) behaves as a source of a strong electrophile, N“), and a chloride nucleophile. Nitrosyl chloride readily adds to olefins to give an electrophilic addition product. What is the expected product of the following reaction? 2 pts. CH3CHZCH=CH2 NOCI Product CH 0') 12. (2 pts.) Outline the'steps in a synthesis of CHCHZCHzcECH _\/ C I m from acetylene and any additional reagents desired MEL,“ 3% m: act-'3 CH 3 >cl+ CH 1 Gib-'X CH 3 Prm'wai' ...
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