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exam1sp09key - Name 'KE y Examination #1 — Feb 4, 2009...

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Unformatted text preview: Name 'KE y Examination #1 — Feb 4, 2009 CH222 - 53 — Org. Chem. II 150 Total Points I. CePA,set) Mechanisms. Write the complete (all arrows, charges, intermediates, transition states for only those reactions which are classified as E2 or S N 2) for the formation of the major products of following reactions. You may choose to answer 4 of the 6 mechanisms. Write OMIT on any problem that you don't want graded. Show any necessary stereochemistry using bold and dashed arrows. (15 points each) (A) + HBr, I1202 CH2CH3 4-0-0-14 2 140 • 1L-i _`EPOS WO* + 14-6( 14014 4- 'Erb-j tr• Y Irm c..446443 H-6r (B) + Br2 , H2O re rtzAws mPrei<ovmKtAl By 44-DlYtI 6^F HO ;By I 1 Icat (C) 1 et7\ H Nit —HC' C-443 r (D) —446 &f- c-443 H A Cannot- be. revrove sInce. rt- is cis kt), CA LeamemYtnt c143 1-.9s s c ' t 'c-k b yLe.l8s a eat 1a4 at ky. trys, VYtabcsr yt clAkcaL'"3 tA134- 2 (F) -•-•-oF_I ol -if`ts 4R sp 1113r C(i r /■-'... ,-i-i Li A( 6Vf - - - C-, - - -p er w Ife o //..-431, + 1-)2_0 Y st , 1-1 eive, it 4 r( (F) 7 _via) 7 \\_____,,c03 --' \ 11. Write the major product(s) of the following reactions. Show the stereochemistry of the product using bold and dashed wedges where necessary. (3 points per product) 14 (A) + 1-113r, 1-1202 ANcil mA(va) Awn) 1-k Br 12acixeoi S/nkriwgctiCA!te CI (B) C CH2CH3 H3C CH3 I teat 0)43\ 0,43 e -44613 co •-•-r 643 Trans markou. 1140 15r Old (C) + 13r 2, H2O ow c4-13 51, NaOH spor..1-pe (D) 1:6"0A43 OAS -4-tycJytxtilccii (E) 0s04.1-1202 CH2CH3 (F) WaYk- JcatP/A Ot 1-1-014 TlakS (1) Hg(0Ac)2,1:120 (2) Na13114 (G) H', C113CH201I mark .04dcra 14 03/4a-13 (H) i nis 1.) QF H a)61 BH 3 , H202 Ck43 CA13 0 14 ?ow N.bigi % H 2 C H 3.4,1 fey, Br t0 (I) atk E2 1/1CH 2 Clir + OK \ A""/1"/CH 3 11/4 Wkk( n temp 5 r100.1.1)e . Cts-W8( X mark ii‘k 1-1 0 C4-13 ihravt33 (1) Hg(OAc) 2 , CI-130H (J) (2) NaBH4 14 OC1-13 eirewts ese- fant• (K) + Br2 so?. (L) KM110 4 , - 01-1 C1s CI ( M) H 3C — CH—CH—CH 3 CH3 + NH2 F1 — CH GI-1g 1114 trY C°3 mosi- (1\1 ) OH + Br eare6o•r 11)0 4 ' Aitet-iv rYlakt OH LAAAD aertrz teavi.n5_ rtf 6 (0) OII Heat (P) + I [2s04 (Q) Br 2 , CH3011 igNr 0,030 1\40444", 7 Ill. For the reactions given in Part II show below, indicate whether they are: a. Stereoselective ONLY b. Regioselective ONLY c. BOTH Stereoselective and Regioselective d. Neither Stereoselective or Regioselective USE THE LETTERS ABOVE PLEASE !!! (3 points each) (A) '13 (C) (1 St Rxn) C.... (D) (E) A Ac (F) '6, (G) (H) A (0) 1) (K) A 13 (L) (Q) 1) C" ...
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This note was uploaded on 03/06/2010 for the course CH 222 taught by Professor Dr.nichols during the Spring '10 term at John Carroll.

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