14D_w11_finalB

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

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
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
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Image of page 2
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 03/12/2012 for the course CHEM 14D taught by Professor Hardinger during the Winter '08 term at UCLA.

Page1 / 6

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

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online