Exam 4 Solution Key

Exam 4 Solution Key - Chem 10172, Spring 2008 (1) EXAM 4...

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Chem 10172, Spring 2008 EXAM 4 KEY April 10, 2008 1 (1) When t -butyl bromide is stirred in 80% ethanol-20% water solution at 45˚ C, a mixture of three products is formed, as shown below: 80% EtOH 20% H 2 O 45 ºC Product 1 58% yield Product 2 29% yield Product 3 13% yield Br OH OEt (a) (8 pts.) Write a detailed mechanism, using curved-arrow notation, for the formation of Product 3 . Br CH 3 CH 2 H 3 C H O H H (Br - or EtOH might also act as base in this step) (b) (12 pts.) For each of the two given alterations in the reaction conditions, circle the expected effect on the rate of disappearance of alkyl halide and on the yield of Product 3 , as compared to the original reaction conditions given above. Change in Reaction Conditions Effect on Rate of Disappearance of Reactant Effect on Yield of Product 3 t BuI is used in place of t BuBr Rate would increase Rate would decrease Rate would stay the same Yield of 3 would increase Yield of 3 would decrease Yield of 3 would stay the same The reaction is conducted in 80% EtOH/20% 1 M aqueous NaOH solution Rate would increase Rate would decrease Rate would stay the same Yield of 3 would increase Yield of 3 would decrease Yield of 3 would stay the same
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Chem 10172, Spring 2008 EXAM 4 KEY April 10, 2008 2 (2) Predict the major organic products of the following reactions, or (for part e) a set of
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Exam 4 Solution Key - Chem 10172, Spring 2008 (1) EXAM 4...

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