Exam4-key

Exam4-key - CHEMISTRY 2261 EXAM 4 November 18, 2009...

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CHEMISTRY 2261 November 18, 2009 EXAM 4 NAME (PRINT)____________________________________________ 123456789 1 0 1 1 TOTAL 12 (B.Q.) LIST number Answer Key 1. (12 pts, 3 pts ea) Give the major product formed in each of the following E2 elimination reactions. EtO Na + EtOH + + + a) b) c) d) Me F ΔΔ Δ Δ Br Cl Ph 2. (5 pts) Arrange the following alkyl halides in order of increasing ratio of E2 to S N 2 products observed in the reaction of each with sodium ethoxide in ethanol. A B C D increasing E2/S N 2 ratio <<< E < most S N 2 most E2 B C A E D H only E2 , no S N 2 S N 2 , no E2 3. (6 pts, 3 pts ea) Give the major product of each of the following substitution reactions. H 2 O NaN 3 acetone N 3 OH There are actually two rearrangements possible for the S N 1 reaction in part b (this was unintended). Showing products from either, or both, got you full points.
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2 4. ( 5 pts ) Rank the following alkyl bromides in order of reactivity using numbers 1-5 (1 = most reactive; 5 = least reactive) in an S N 2 reaction where the alkyl bromide is converted to the corresponding nitrile: NaCN NaBr RB r acetone RC N + Br N 12 34 5 or 2 3 5. (4 pts) Rank the following alkyl bromides in order of reactivity using numbers 1-4 (1 = most reactive; 4 = least reactive) in an S N 1 reaction where the alkyl bromide is converted to the corresponding alcohol: (see explanation on last page of answer key) H 2 O HBr r RO H + 1 2 6. ( 4 pts ) Indicate (in the box) for each of the following trends, whether the trend is observed for polar protic solvents, polar aprotic solvents, both types of solvent, or neither type of solvent.
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Exam4-key - CHEMISTRY 2261 EXAM 4 November 18, 2009...

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