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CH223_001Exam1 - a detailed arrow-pushing mechanism and as...

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1 CH223-001 Spring 2012 First Exam 13 Feb. 2012 Name: 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 pK a 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.)
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2 Problem 1 (25 points). The sulfonation of furan (using SO 3 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
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Unformatted text preview: a detailed arrow-pushing mechanism and as few words as possible. Show all relevant resonance structures. O O O not SO 3 H SO 3 H SO 3 , pyridine 3 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. CO 2 H CH 2 I 2 , Zn/Cu 1. CH 3 C(O)Cl, AlCl 3 2. CH 3 Li Br 2 , FeBr 3 , ∆ OH CF 3 OH 4 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 sp 2-hybridized cations can not be formed. H 3 CO ? H 3 CO CH 3 CH 2 5 Problem 4 (25 points). Here are a few from the homework/supplementary problems…. Cl CH 3 O H 3 CO O CH 3 N PhMgBr (2 equiv.) Br CH 3 1. Li° 2. CuI 3. H 3 C-CH 2-CH 2-CH 2 I Cl O H 3 CO H 3 CO AlCl 3 , ∆ 6 7...
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