3. (8 points total) (a) (3 points) What is the rate law for an SN2 reaction? (b)

Question

3. (8 points total) (a) (3 points) What is the rate law for an SN2 reaction? (b) (5 points) What happens to the reaction rate when each of the below circumstances is applied to th following SN2 reaction? (Circle one answer for each.) OTs NaOMe DMSO tno change no change t no change 1 no change t no change i. the leaving group is changed from OTs to OH the temperature is raised to 60°C ii. the concentration of NaOMe is increased 5-fold iv. the phenyl ring is changed to a tert-butyl group v. the nucleophile is changed from NaOMe to Nal

Explanation / Answer

3 a. Rate = K [R-X] [Nu].

b. i. Rate decreases because OH is a bad leaving group.

ii. Rate decreases because increase temperature increases the elimination product.

iii. Rate increases 5 times because Rate = K [R-X] [5Nu] = Rate = 5 x K [R-X] [Nu].

iv. Rate decreases because steric hindrance increase at beta carbon of alkyl halide.

v. Rate decreases because I - is weak nucleophile than -OMe.

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