CHEM 239 ex2_key - Chemistry 239 Autumn, 2004 Sample Exam 2...

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Unformatted text preview: Chemistry 239 Autumn, 2004 Sample Exam 2 Answer Key Your name: ; Student #: Sign here to indicate your approval of public return of your paper: 1 (18 pts.) Give structures or systematic names for the compounds below. CH3CH20C02CH20H3 CH3CHZCH2NH2 CH3CH2N(CH3)2 N,N-dimethylethylamine or N,N-dimethylethanamine propylamine diethyl carbonate 0' propanamine \ NH / 2 N pyridine an aryl anion 2 (5 pts.) Complete a balanced equation for a proton transfer between the reactants below, label the stronger and weaker acids involved, and indicate whether the position of equilibrium is favorable (to the right) or unfavorable (to the left). PhNH3+ + MeNH2 41> PhNH2 + MeNH3+ stronger acid -—-> weaker acid <— [pKa 5] favorable [pKa 1o] Chem 239 Autumn, 2004 Sample Exam 2 Answer Key p. 2 3 (28 pts.) In the reactions below fill in the missing items (starting materia1[s], reagents and conditions over the arrow, or main organic product[s]). 1. Na+,'OEt “30+ CH2(C02Et)2 —-————> PhCH2CH(C02Et)2 —+ PhCHZCHzCOZH 2. PhCHzBr heat 1. Na+,'OEt + HCOzEt I cno Ph(cH2)2C°2Et PhCH2(l3HCO Et ’ 2 2. H30+ 1. Na+,'0Et 0% o§ CH(COZCH3)2 CH2(C020H3)2 + I 2. H30+ 1. LiAIH4, 2. H20 phCN —————————_> PhCHzNHz Cl OH Cl PhNH2 ———_» th=N OH 0 o // 1. KOH // OH'IHZO NH ——————> NCHzPh —————> PhCHzNHz \ 2. PhCH2X \ CH3N H2, H2/cat. CH3COCH3 —‘_—"———"'—> (CH3)2CHNHCH3 Chem 239 Autumn, 2004 Sample Exam 2 Answer Key p. 3 m 4 (10 pts.) Draw a curved arrow mechanism for the reaction below. Show all steps, unshared electron pairs and formal charges. 0 I ‘ l+ heat ““—‘—> + CH3—— *CH3 I O 0 CH3 5 (10 pts.) Give your interpretation each item of evidence below and propose a structure for a compound I. a) I had a molecular ion in peak its mass spectrum at m/z = 87. b) The IR spectrum of I showed two peaks between 3300-3500 cm-l. c) I gave the nmr spectrum below — show your peak assignments and label the multiplicity of all peaks. 44-5 contains an N [odd mass] c) | = HZNCH(C3)CH(C3)2 b) primary amine [C5H13N = 60 +13 +14 = 87] Chem 239 Autumn, 2004 Sample Exam 2 Answer Key p. 4 6 (10 pts.) Show how you would carry out the synthesis below. (Show the main product after each step, with reagents and any special conditions over each reaction arrow.) Me EtOCO EtO OEt 7 (10 pts.) Show how you would carry out the synthesis below. (Show the main product after each step, with reagents and any special conditions over each reaction arrow.) Br Br Br from <:>7NH2 Chem 239 Autumn, 2004 Sample Exam 2 Answer Key p. 5 8 (9 pts.) Draw a curved arrow mechanism for the reaction below. Show all steps, unshared electron pairs and formal charges. Then use the appropriate structures to explain why no similar reaction occurs with the meta isomer of the starting material. COMe COMe <j MeO', heat -——-—-—-—-—-—————-———> Br 2 other contributing structures with negative charge in ring extra resonance stabilization of this type not possible for the meta isomer ...
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This note was uploaded on 06/29/2008 for the course CHEM 239 taught by Professor Sasaki during the Winter '06 term at University of Washington.

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CHEM 239 ex2_key - Chemistry 239 Autumn, 2004 Sample Exam 2...

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