Exam_2_Green_Key - CEM251/Fall 2010/Second Hour Exem Him”...

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Unformatted text preview: CEM251/Fall 2010/Second Hour] Exem....... ,. Him”. fl (pagej) ___ 20 . t t t I Eyre/gig tew QM ( pom s o a) Me: M t 1. Draw the strLJcture of the foHowing compounds: a) t-butylAalcohol (Cl—“‘3‘, C. .— 53H 2 pts. b) 2-methyI-1-butanol C) an 3-methoxypentane 0” 4-phenyleyclohexanol 6) ethyl methyl ether f) (Z)-3-chl0ro-2-hexene g) _ (E)-2-hexene h) styrene i) 1-hexyne J) 2-methy-lokirane ' CEM25‘l/Fall 2010/Second Hourly Exam ....... (page 2) (20 points total) 2. . Draw the structure of the major substitution product(s) of the following reactions. L" Show stereochemistry carefully. a) 5H3 b) Br ."."CH3 H CH30H (3N1) \r—r d)‘ CH3 CH3CH2cH2_c<-H 2 pts. CEM251/Fall 2010/Second Hourly Exam.......(page 3) (10 points total) 3. Draw the structure of the major elimination groduct of the following reactions. \‘r-. a) CH 3 1) 30012 ———> “O 2) A, KOH (E2) m CH 3a.,1‘) 30012 ——-—- (5N2)- HO 2) A, KQH (E2) C) CH3 HO ci‘i3 k. 0%; /CH3 CH3 /¢ 0:0 \c=c / V / \ H _ 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 2 pts. / (3N2) A 2) A. KOH ( ' CH CH3 H \ 1) CH3—@—SOCl2 a 2 pts. 2) A,. KOH IL - . (E2) CEM251/Fall 2010/Second Hourly Exam ....... (page 4) _ (12 points total) 5. CH3 — A) CHBCHZBY + CH—ONa ———> / CH3 ' CH3 \ B) CH—Br + CHacHZONa ——D- / CH3 Which one of the above reactions (A or B) (2 Dis-l will give the higher yield of ethyl F} isopropyl ether? 6. - CH2(+) . CH3 H CH3 x ' _ v - z x; _ _ a) Which of the above carbocations (X, Y or Z) \I/ (2 ms”) is most stable? .. b) 'Which of the above (X, Y or Y) is a 1°_ K -(2 Pia) carbocation? 7. The following reaction occurs by an E1 mechanism. Draw appropriate structures in the boxes. _ (2 pts.) (2 ms.) 1,2 Hydride shift CEM251/Fall 2010/Second Hourly Exam ....... (page 5) (22 points total) 8. Draw the structure of the major organic product: a) CH3 b) CH3 HBr _> 0) . \ CH CH C_CH ‘ 1) 3H3 ’ Cf" 3 2 — 2)NaOH, c_.Q_ up H202 d) CH30H2 \ _ /H Br2 c—c —. / \ H20 CH3 CH3 9) H\C: CH/ H20 H so HC/ —C\CH(CH3)2 .2 4 f) 1) 13H3 ——> 2) NaOH CH36H2 H202 Q) B CHacHZCHQCECH . r2 excess h) _ H20 HC:CCH2—@ H so 2 4s HES Q4 major product CEM251/Fall 20tO/Second Hourly Exam ....... (page 6) (12 points total) . 9. Draw the structure of the major organic product: a) - 2 pts. 2 pts. A CH CH OCH CH '3' 2 2 2 3 (excess) b) O 2 pts. CH / \ / 2 H2804 CH3 0) O / \ /¢ NaOCHZCI-la CH2 0 CH30HZOH d) 2 pts. Elir CH3CH20H2—CH A - I NaNH2 Br (excess) Elimination Product 10. Compound X has the molecular formula C10H14Cl20. X has exactly one ring. How many 31: bonds are present in the structure of X? -2 ptS. CEM251/Fall 2010/Second Hourly Exam ....... (page 7) (4 points total) 0 O H H (2 PtS-) Nitrosyl chloride (N— CI) behaves as a source of a strong electrophiie, 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? H 2 pts. \C=CH2 NOCl Product . CHZCH2CECH 12. (2 pts.) Outline the steps In a synthesrs of g from acetylene and any additional reagents desired. M&,Mfi3_flk a £5125“ mix ”g t “W Ca new (+3- ...
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