14D_w09_finalB

14D_w09_finalB - C h e m is t r y 1 4 D W in t e r 2 0 0 9...

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Chemistry 14D Winter 2009 Final Exam Part B Page 1 The questions on this page refer to this S N 2 reaction: Molecule A 1. (4) Complete this statement by filling in the blanks, using no more than three words in each case: Triflate (CF 3 SO 3 - ) is an excellent leaving group but a poor nucleophile due to ____________________________ and ____________________________. 2. (2) Complete this drawing of the reaction’s transition state structure: 3. (8) Circle the appropriate effect on the reaction rate when the following changes are made to molecule A. The changes are not cumulative; for example the change made in part (a) does not carry on to part (b). (a) NaSCH 3 changed to NaSPh Rate is faster Rate is slower No significant change in rate (b) R–OSO 2 CF 3 changed to R–Br Rate is faster Rate is slower No significant change in rate (c) R–CH 3 changed to R–C(CH 3 ) 3 Rate is faster Rate is slower No significant change in rate (d) DMF is changed to acetone Rate is faster Rate is slower No significant change in rate 4. (18) Some changes in the reaction cause a shift in mechanism. For each change listed below, circle the name of
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14D_w09_finalB - C h e m is t r y 1 4 D W in t e r 2 0 0 9...

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