14D_w12_e01 - Chemistry 14D Winter 2012 Midterm Exam 1 1(4...

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Chemistry 14D Winter 2012 Midterm Exam 1 Page 1 Page 1 score = 1. (4) Define “S N 2 reaction,” without using an example, and without referring to kinetics. 2. (5) Write the mechanism and product(s) for this S N 2 reaction: I H CH 3 CH 3 S Na CH 3 OH 3. (2) Circle the correct representation(s) of a transition state from question 2. I SCH 3 CH 3 CH 2 Ph H δ δ I SCH 3 H CH 2 Ph CH 3 δ δ I SCH 3 CH 3 PhCH 2 H δ δ I SCH 3 CH 3 PhCH 2 H δ δ 4. (2) Circle the best explanation(s) for backside attack and stereochemical inversion in the reaction of question 2. (a) The backside has less steric hindrance. (b) The nucleophile attacks the carbon-leaving group σ * orbital. (c) The nucleophile and leaving group both have a δ - charge in the transition state. (d) The question is irrelevant because inversion does not occur in this case. 5. (2) In the reaction of question 2, doubling the concentration of NaSCH 3 causes the react rate to be (circle one)... cut in half doubled quadrupled not significantly changed 6. (8) Circle the effect on rate of the reaction in question 2 when the following changes are made. (a) NaSCH 3 changed to NaF: slower faster no significant change (b) CH 3 OH changed to CH 3 CH 2 CH 2 OH: slower faster no significant change (c) NaSCH 3 changed to NaSC(CH 3 ) 3 : slower faster no significant change (d) CH 3
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