14D_f11_finalB

14D_f11_finalB - Chemistry 14D Fall 2011 Final Part B Page...

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Chemistry 14D Fall 2011 Final Part B Page 1 Page 1 score = Mechlorethamine is an anticancer drug that alkylates DNA twice. This reaction is irreversible, so the DNA is permanently damaged. N Cl Cl H H Mechlorethamine Questions 1–3 refer to this hypothetical S N 2 reaction for mechlorethamine manufacture: N Cl Cl H H NH 3 DMF ICH 2 CH 2 Cl 1. (6) Write the mechanism for this reaction. Do not include any transition states. 2. (8) Complete each sentence by adding no more than twenty words in each case. (a) (ICH 2 CH 2 ) 2 NH 2 + is not produced in this reaction because. .. (b) This reaction does not proceed via an S N 1 mechanism because. .. 3. (3) Circle the appropriate effect on the rate of the mechlorethamine manufacture reaction caused by each change listed. (a) NH 3 changed to PhNH 2 : Rate increases Rate decreases Not much change (b) DMF changed to hexane: Rate increases Rate decreases Not much change (c) ClCH 2 CH 2 I changed to Cl I Rate increases Rate decreases No change 4. (2) Circle the best nucleophile in DMF: H 2 O HO - F - CH 3 CO 2 - 5. (2) Draw a carbocation that has exactly five carbons plus any number of hydrogen atoms (and no other elements), and is obviously more stable than a cyclopentyl carbocation. Cyclopentyl carbocation
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Chemistry 14D Fall 2011 Final Part B Page 2 Page 2 score = 6. (2) Draw the mostly likely product from rearrangement of this carbocation. Include curved arrows. OCH
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This note was uploaded on 03/12/2012 for the course CHEM 14D taught by Professor Hardinger during the Winter '08 term at UCLA.

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14D_f11_finalB - Chemistry 14D Fall 2011 Final Part B Page...

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