PS Session 1 08.27.10

PS Session 1 08.27.10 - For instance, if a chiral product...

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1 Problem-Solving Session Worksheet Chemistry 262, Fall 2010 Session 1: 26 August 2010 Part 1: Review of Chemistry 261 1. Illustrate the major organic product of each reaction. Circle the mechanism. 2. Johnny B. Chiral, a chemist at PU, treated (2 S , 3 S )-2-bromo-3-methylpentane with an alkoxide base and obtained a product whose 1 H NMR spectrum contained the following resonances: δ 1.06 (3H), 1.71 (3H), 1.72 (3H), 2.00 (2H), 5.20 (1H). What is the product? Suggest an alkoxide base that Johnny might have used. Br + S N 1 S N 2 E1 E2 O Br + S N 1 S N 2 E1 E2 C N + H 2 SO 4 S N 1 S N 2 E1 E2 OH
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2 3. Provide the missing stuff below. Illustrate the stereochemistry of the reaction where appropriate.
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Unformatted text preview: For instance, if a chiral product is formed as a racemate, write the word racemic under your product. H 3 CO 1. Hg(OAc) 2 , H 2 O 2. NaBH 4 , NaOH, H 2 O Br 2 , H 2 O 1. Na , liquid NH 3 2. H 2 O to adjust to pH 7 3. O 3 4. (CH 3 ) 2 S H O O H H H O 2 + OH OH racemic OH OH Br LDA Br 2 , hv 3 4. Provide mechanisms. OH multiple stereoisomers H 2 SO 4 H 2 O 4 Part 2: Chemistry 262 Material 1. Provide a synthesis of racemic-2-butanol from propene, methane, and anything else you choose. 2. Predict the products. Br 1. 2 Li(0), diethyl ether 2. D 2 O Cl 1. Mg(0), diethyl ether 2. O NH 2 3. H 3 O +...
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PS Session 1 08.27.10 - For instance, if a chiral product...

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