14D_w11_finalB - Chemistry 14D Winter 2011 Final Exam Part...

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Winter 2011 Final Exam Part B Page 1 Page 1 score = 2,4,6-Trinitrophenol is also known as picric acid because its OH group is strongly acidic (p K a = 0.38). In the following questions, picric acid is abbreviated as PicOH, and its conjugate base as PicO - . OH NO 2 O 2 N NO 2 Picric acid (PicOH) Questions 1–4 refer to the nucleophilic substitution reaction of sodium picrate and ( R )-2-bromo-2-deuteriobutane. (D = deuterium = 2 H; behaves just like 'normal' 1 H hydrogen.) Br H D acetone OPic PicO - + Na D H 1. (1) Circle the most likely mechanism for this reaction: S N 2 S N 1 2. (2) Write the mechanism for this reaction. Do not include any transition states. 3. (2) Circle the correct statement concerning the stereochemical configuration of the reaction product: Pure R Pure S A mixture of R and S Cannot determine 4. (3) Complete this sentence by adding no more than fifteen words : A significant reason why this reaction does not occur by the mechanism that I did not circle in question 1 is. .. 5. (6) The conjugate base of picric acid (PicO - ) is a poorer nucleophile than (CH 3 ) 3 CO-. Using no more than twenty words in each case, complete these two very different explanations. Reason #1 : Compared to (CH 3 ) 3 CO - , PicO - is a poorer nucleophile because PicO - has. .. Reason #2
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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_w11_finalB - Chemistry 14D Winter 2011 Final Exam Part...

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