Solved Exam 2 Questions - Organic Chemistry 1 | CHEM 3311, Exams of Organic Chemistry

Download Solved Exam 2 Questions - Organic Chemistry 1 | CHEM 3311 and more Exams Organic Chemistry in PDF only on Docsity! Chemistry 3311-100 Organic Chemistry /Dr. Barney Ellison Thursday: Mar. 13" @ 7:00pm —> 9:00/2°¢ Exam/ Math 100 Name: len (please print) 1.(20 pts) Predict the major organic product of each of the following reactions. x as Chy ‘ CH;CH,O-Na* cy ™™ c tly ethanol, A a xe OW . a) L YY Ye yy (CH,);CO-Na* cbe ———— (CH),;COH, A b) C(CH,),Ce ¢) HOOC—CH, gy, HOOC—cH, COOH H,SO, 140-145° CoH.O, ene cor C. _cooh \ els ~¢ ool 4. (10 pts) Dehydration of (CH;),C- -C(OH)(CH,)-C(CH,);_ gave two alkenes, A and B. Ozonolysis of the lower boiling alkene A gave HCHO and 2,2,4,4-tetramethyl-2-pentanone. Ozonolysis of B gave HCHO and 3,3,4,4-tetramethyl-2-pentanone. Identify A and B. os ll HC. -C—C(CH,); (H,0),C~ “Nec, i CH, 2,2,4,4-tetramethy!-3-pentanone 3,3,4,4-tetrametyl-2-pentanone ths i cls ol cly A SO4 , > Nt an Ure - = coh => CH o— 7 ‘eH ‘Ut Cfk. ¢ 3 cH, ls . 7 3 = a \> At Ze VY Cy (Hy 7 th ch> \ \ —C ih 3 3 cA + \ \ i \ Ch, ~ ‘ ~ K aN Cc y va SC 8 CW é HL ch 4* 7) ® 3 4 Lit, cH Chy, ¢ ° \o \ C cat (H 4 2 zn are ey mene O C _ cm 4hche 3 o Os-4 Vay Uy \ chy + WES 5. (20 pts) Suggest a sequence of reactions for preparing each of the following compounds from the indicated starting materials. a) 1-propanol from 2-propanol CHsCih: CA-08 4 B,We | ool of N2S% \ _ —-C(\= ch z Cacia, A > Ch, b) —1,2-dibromopropane from 2-bromopropane be \ (yh Ch, ~4 (Hy | capo / +o WY ¢ As CRCH= Che eae ce) 1,2-epoxypropane from 2-propanol ok (Ks cys | 5% JA Vv G 6 Chy~ «COR as ch cl Me Ch—¢ y=ch, — d) __ trans-1,2-dichlorocyclopentane from cyclopentane sy CCha, a Vs Q KS f "eR