Help Session Problem Set 3-21-08

Help Session Problem Set 3-21-08 - a b c d e Cl O O OH 1...

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1 Chem 2210 Organic I Exam III – 03/21/08 – 9:05-9:55 a.m. PRACTICE Name: ___________________________________________ Section: __________________________________________ This exam has 14 pages total. Pages 13-14 are scratch paper. Page #2 Page #3 Page #4 Page #5 Page #6 Page #7 Page #8 Page #9 Page #10 Total
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2 1. Draw the most stable isomers of the following compounds. 2. Name the following compounds. b) 3. The following two compounds have large dipole moments. Please show the direction of the dipole (using a dipole arrow) and a resonance structure that justifies the dipole moment. (Note: lone pairs are implied.) a) 3-methylpentene isopropylcyclopentene Et NC OH OMe NO 2
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3 4. Predict the product(s) of each reaction. a) b) c) d) e) 750 o C Me Me iPr OH H 2 SO 4 ,80 o C Me NaOEt,25 o C Br 1) B 2 H 6 ,diglyme 2) H 2 O 2 ,NaOH Me catalytic HBr (0.01 eq)
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4 5) Predict the product(s) of each reaction.
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Unformatted text preview: a) b) c) d) e) Cl O O OH 1 equivalent Me HBr acetic acid Me Br 2 , H 2 O Br 2 CHCl 3 Me CN Me 1) Ozone, MeOH 2) H 2 O, Zn Me 5 6. For the following reaction provide product arising from a S N 1, S N 2, E1 or E2 mechanism. Draw the rate-determining transition states leading to each product. Nuc Me Br Me S N 1 S N 1 T.S. S S N 2 S N 2 T.S. E1 E1 T.S. E2 E2 T.S. 6 7. Provide an arrow pushing mechanism for the following reaction. Br 2 /CHCl 3 Br Br Br Br + 7 8. Provide an arrow pushing mechanism for the following reaction. Me H OH O O O O H Me HO 8 9. Explain the following observation by using pKa data, showing the intermediates. O O O Δ Δ 9 10. Cyanide anion is a strong nucleophile. With that knowledge synthesize the following compound from the starting materials provided. HO O...
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This homework help was uploaded on 04/17/2008 for the course CHM 2210 taught by Professor Mcquade during the Spring '08 term at FSU.

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Help Session Problem Set 3-21-08 - a b c d e Cl O O OH 1...

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