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A november 3, 2008 in-class quiz for chemistry 231, elementary organic chemistry, focusing on sn2-type reactions. Students are asked to write a rate expression, draw a transition state diagram, explain why the sn2 mechanism is followed, rank organohalides and nucleophiles in order of reactivity, and draw the major organic product.
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NAME: November 3, 2008
CH 3 —I + :NH 3 [CH 3 —NH 3 ]+^ + I-
a. (4 pts) Given that this is a second-order process (Hint: It is a concerted process), write a reasonable rate expression for the above reaction. Place your answer in the box provided.
b. (8 pts) In the space provided below, draw a three-dimensional diagram showing the transition state for the SN2-type reaction between iodomethane and ammonia. Be certain to indicate both the geometry and bond angles at carbon in your model.
c. (8 pts) Why do you think that this process proceeds by way of the SN2 reaction mechanism? Be concise.
Rate =
Br Br I Br
NaN 3 NaO 2 CCH 3 NaCN NaI
Br (^) NaSCH 3 DMSO
OH (^) NaCl Acetone