118CMT1 - C N P (cat), Br 2 (excess) 1)MeMgBr, THF 2) H 3 O...

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1 Chemistry 118 C Fall 2006 First Midterms Wed. October 18, 2006 Instructor: Lievens This exam contains six (6) pages and six (6) problems. Please make sure that your copy contains all six pages. If there is a problem, please tell the exam administrator prior to beginning. Please answer all questions. Remember that UCDavis Code of Academic Conduct applies to this exam and all other graded work in this class. Name: ________________________________________________________________ Last First MI Student ID. # __________________________________________________________ T.A./ Lab Section: ______________________________________________________ Problem # Points 1 2 3 4 5 6 Total (100)
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2 1. (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. NH 2 O H 2 O, 20 0 C O OCH 2 CH 3 Enzyme OH O OEt O
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Unformatted text preview: C N P (cat), Br 2 (excess) 1)MeMgBr, THF 2) H 3 O + , H 2 O 1) LDA, THF, -78 C 2) (CH 3 ) 2 CHCH 2 Cl B) A) D) E) F) C) 1) BrMgEt, ether 2) H 2 SO 4 , H 2 O O S HO O Protein O S Protein 3 2. (20 pts.). Show detailed reaction mechanisms for each of the following reactions. Include the structure of the expected products. A) R OH O SOCl 2 B) R NH 2 O NaOH, Br 2 , H 2 O 4 3. (22 pts) Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. A) R R N OH B) R O OCH 3 R O 5 4. (8 pts). Rank the following compounds in decreasing order of acidity. H 3 C H O ClH 2 C OH O F 3 C OH O H 3 C OH O H 3 C N(CH 3 ) 2 O Cl 3 C OH O Cl O OH HO S OH O O A B C D E F G H Highly Acidic Moderately Acidic Poorly Acidic 5. (6 pts.) Provide the systematic names of each of the following compounds. Cl O B) A) C) F 3 C OCH 3 O N O...
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118CMT1 - C N P (cat), Br 2 (excess) 1)MeMgBr, THF 2) H 3 O...

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