ProblemSet4 - Biochemistry 704 Problem Set 5 Due 1 In water...

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Biochemistry 704 Problem Set 5 Due 03/11/2008 1. In water at 35 °C, the rate constants for the aminolysis (by ethylamine and decylamine) and hydrolysis (by hydroxide ion) of an acetate and decanoate ester are as follows. Rate Constant for Aminolysis or Hydrolysis ( k ; M -1 s -1 ) O O NO 2 O O NO 2 NH 2 NH 2 39 130 5.7 0.42 9.4 1.2 OH a. Why is the ratio k decylamine / k ethylamine for attack on the decanoate ester »1? b. If the environment were altered by decreasing the dielectric constant of the medium, would this ratio increase or decrease? Explain briefly.
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page 2 of 5 c. Why is the ratio k decanoate ester / k acetate ester for attack by hydroxide ion ‹1? 2. The relief of strain in the transition state can accelerate a chemical reaction. Cyclopropyl bromide has a large amount (25–30 kcal/mol) of ring strain energy. Yet, cyclopropyl bromide undergoes nucleophilic attack by I in acetone (to form cyclopropyl iodide) 10 4 times more slowly than does isopropyl bromide. Explain. What lesson can be learned
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ProblemSet4 - Biochemistry 704 Problem Set 5 Due 1 In water...

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