CH223_001Exam1Key - SCH223-001 Spring 2012 First Exam 13...

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Unformatted text preview: SCH223-001 ! Spring 2012 First Exam 13 Feb. 2012 Name: E‘fiprm KY3“ Student ID: Signature: This exam has 4 problems, each worth 25 points. You have 50 minutes to complete this exam. You may not talk to each other during the exam. You may not use notes, books or any electronic assistance. Read all of the questions carefully before you begin. It is recommended that you start with the problem(s) that seem easiest to you. There are two blank pages at the end of the exam if you need them. Do not separate the pages of your exam. Make sure your answers are clear and legible. Please do not use red ink on the exam. Some common CH223 pKal values: 1° alkane C-H ~62 amine N-H ~32 aryl/alkenyl C-H ~44 alcohol/water O-H ~16 benzylic/allylic C-H ~41 ammonium N-H ~12 alkyne C-H ~25 phenol ~10 (You shouldn’t need these.) Problem 1 (25 points). The sulfonation of furan (using 803 in pyridine) gives furan-2—sulfonic acid as the major product. Little or no furan-3-sulfonic acid is formed. Please explain this selectivity, using a detailed arrow-pushing mechanism and as few words as possible. Show all relevant resonance structures. 0 803, pyridine 0 30 H O i\ /7 —” \ / 3 "0‘ i\ /{ SO3H ‘3) a (\J J ——‘*'P <\ [git <——7 @<:_7‘H H </_ 5936) e) 6% a o -H o ('1) $17“ —-° <~__« 5°?» 6) o c. / é) / (uh -—-» xx. .509 e—> \\__: so? 0:250 fi H (9-?- D /b <‘ a e ”" $.42 -—.... so! 3) O H 3 Gites—Tex. Resoemce STPH3\L\"1‘:’&-T\OM as MONK. ianLMeDuH‘E LEWIRG To 1—5uLanxc aux-D ('5 COIA‘T‘asVBuTlNB meMkfici smumais\ Tums “Tue—1" LEA-fimmcs 'T‘D 7;— suLPon-MC. A—C-tt) (Z use NANCE... amenities) Problem 2 (25 points). Please fill in the missing component(s) for each of the following reactions. For reactions missing the reagents, more than one set of reagents may be required. CL "°‘ “>9 1 Cf” OH N GMT, “Pa-$559111. COZH (KaLV-a6 -$U~u'fi EFMOAB CF3 © Brg, FeBr3, A \ CHQIQ, zn/CU H H \"L H © 1. CH30(O)CI, AICI3 2. CH3Li Problem 3 (25 points). Please propose a synthesis of the styrene derivative shown below, beginning with anisole. You may use any additional neutral organic reagents (and any inorganic reagents) you need. Remember that electrophilic aromatic alkylation does not work with alkenyl halides because sp2~hybridized cations can not be formed. 9 H300 _ H3CO -———>— O CH3 Nunmous ’POS‘EMBLf MBMEES. Two E-‘fiMx’?k£‘-’a '. “‘ ’3 1;. Cu: at l, ,? “WA CH3 “ECG; K 0. ° ‘ A CDC—H Duri- C. 6.14 1 “1’ 1’ 1’ 6“; 3 ._ ,0 .. x?) Pduslb \fi um \ I / CH “32 CH; “3‘3 3 Problem 4 (25 points). Here are a few from problems... the homework/supplementary Hacokcfl PhMgBr (2 equiv.) E”) Li° 2. Cul Br/VCHa 3. HSC-CHa-CHg-CHBI AICI3, A H300 0 Cl ...
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