HT2ans-05 - Answers to HT#2, Chemistry 301X, 2005 1. The...

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Answers to HT#2, Chemistry 301X, 2005 1. The rate-determining step for the E1 and S N 1 reactions - the ionization shown below - is the same, so the rates must be the same. The E2 and S N 2 reactions have totally different rate-determining steps, so of course their rates are different. Curves can be found all over Chapter 7. H 3 C H 3 C I H 3 C H 3 C I slow step in both E1 and S N 1 H 3 C H 3 C Nu H 2 C H 3 C S N 1 E1 1b. E1, S N 1: pyramidal bridgehead carbocation too unstable to form. E2: The 2 p orbitals of the bridgehead double bond do not overlap - there is no real double bond. S N 2: The nucleophile cannot reach the rear of the putative leaving group. 2. (a) * H H 3 C I CH 2 Cl 2 S N 2 HS H CH 3 I HS * b. S c. R d. you can’t tell.
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e. In this case, changing to a less polar solvent would increase the rate of reaction. The ionic starting material, with a thiolate with a full negative charge, is more stabilized by a polar solvent than is the transition state in which the charge is dispersed. HS
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HT2ans-05 - Answers to HT#2, Chemistry 301X, 2005 1. The...

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