3rd Sample Exam

6 pts cl cl ii substitution and elimination 1

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Unformatted text preview: tic acid H N HO CO2K OH H CO2H tartaric acid CH3 O OH N H2 O O H3CO proline naproxen 4. Circle the more polar alkene. (4 pts) Cl Cl 5. Rank the alkenes in order of increasing stability. (6 pts) Cl Cl II. Substitution and Elimination 1. Give the SN2 product (6 pts each) (a) H Br H C C Ph C H3 C H2 S Na CH3 Ph (b) KOH, DMF Cl OH 2. Give the E2 product (6 pts each) (a) H Br H C C Ph (CH3)3COK CH3 Ph (b) H Br Br H KOH, CH3CH2OH heat 3. Explain the differences in rates using structures. (8 pts) Br KI, acetone Br Br KI, acetone no reaction Br (a) 4. Predict the major product of each E1 elimination. (12 pts) CH3 EtOH, heat Br (b) CH3 OH H2SO4, heat 5. (a) Rank the halides in increasing nucleophilicity in water: (4 pts) KBr, KCl, KI, KF (b) Rank the alkyl halides in increasing reactivity in the SN2 reaction: (4 pts) H2C=CHCH2Br, CH3CH2Br, (CH3)3CCH2Br, (CH3)2CHCH2Br 6. Circle the maj...
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