Exam 02-672239FF-99DF-11D2-A076-0090271E0FF5-572CE-M

Exam 02-672239FF-99DF-11D2-A076-0090271E0FF5-572CE-M - c CO...

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ORGANIC CHEMISTRY CH 313-02 EXAM 2 May 1, 2003 Name:_______________________________________________________ Directions: Place your name on your exam paper. Read each question carefully and answer all questions on your exam paper. Remember: “God began doing a good work in you, and I am sure He will continue it until it is finished when Jesus Christ comes again.” Phil 1:6 (NCV) 1. (10) Name the following compounds. a. NH 2 CO 2 H b. CO 2 H OH c. [(CH 3 ) 3 N + CH 2 CH 2 CH 2 CH 3 ]OH - d. CO 2 H OCCH 3 O e. N 2 + Cl - OH 1
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2. (30) Complete the following reactions. a. NH 2 SO 2 NH 2 1 ) NaNO 2 /HCl 0-5 O C 2 ) OH b. O O 1 ) NaOH 2 ) H 3 O + 2 c. CH 3 Cl NH 2 - NH 3(L) d. OH CO 2 120 o C/100 atm e. OH 1 ) NaOH 2 ) Br 3 ) 200 o C
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3 f. OH CH 3 CCl O g. Product from (f) AlCl 3 heat h. NO 2 Cl 1 ) NaOH/H 2 O 2 ) 125 o C i. F Br 1 ) Mg/THF 2 ) j. NO 2 NO 2 1 ) Sn/HCl 2 ) NaNO 2 /HCl/ 0-5 o C 3 ) NaBF 4
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3. (30) Synthesize the following compounds from the given starting materials. 4 a. CO 2 H OH from b. C O H from
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5 c.
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Unformatted text preview: c. CO 2 H OH from d. I Cl Br from 4. (15) Propose a mechanism for each of the following reactions. 6 e. O NO 2 from a. CH 2 CH 2 CH 2 CH 2 CO 2 CH 2 CH 3 Cl 1 ) XS NaNH 2 /NH 3(L) 2 ) H 3 O + CO 2 C 2 H 5 7 b. NCH 2 CH 2 NHCH 3 CH 3 XS NaNH 2 /NH 3(L) diethyl ether N N CH 3 CH 3 c. CH 2 CH 3 N(CH 3 ) 3 + OH-heat CH 2 CH 3 CHCH 3 (CH 3 ) 3 N 5. (5) For the following reaction, how can you determine whether the reaction is proceeding through the addition-elimination or elimination-addition mechanism? 6. (10) Suggest a synthesis for Diphenadione from 1,1-diphenylacetone and dimethyl 1,2-benzene dicarboxylate, and mechanism for the synthesis. Diphenadione 8 Cl OH KOH/H 2 O 370 o C 1 ) 2 ) H 3 O + O O CCH O...
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