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14D_f09_e01 - Chemistry 14D Fall 2009 Exam 1 Page 1 OK to...

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Chemistry 14D Fall 2009 Exam 1 Page 1 Page 1 score = OK to use ‘Ph’ anywhere on this exam where appropriate. 1. (8) Complete the following S N 2 reaction by drawing the curved arrows, and finish the transition state and product drawings. 2. (14) What happens to the reaction rate when the following changes are made to the reaction of question 1? Write ‘faster’, ‘slower’, or ‘no significant change’ in each blank. The changes are not cumulative . (a) C 6 H 5 S - changed to C 6 F 5 S - : _________________________ (b) C 6 H 5 S - changed to CH 3 S - :_________________________ (c) CH 3 of electrophile changed to (CH 3 ) 3 C: _________________________ (d) CH 3 OH changed to (CH 3 ) 3 COH: _________________________ (e) CH 3 OH changed to acetone: _________________________ (f) I changed to Cl: _________________________ (g) Alkene changed to alkane: _________________________ 3. (7) Circle the better leaving group: Leaving group A Leaving group B Complete these two distinctly different reasons for your choice, by adding no more than twenty words in each case. Reason #1 : This is the better leaving group because... Reason #2 : This is the better leaving group because... 4. (1) Circle the molecule that is the stronger nucleophile in DMF: I H 3 C H S CH 3 OH I C CH 3 Cl Cl Cl Cl H S S O O S S O O
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Chemistry 14D Fall 2009 Exam 1 Page 2 Page 2 score = 5. (3) NMP is a solvent used in many industrial processes, as well as some drug formulations.
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