2006MidtermExam#2

2006MidtermExam#2 - Last Name: First Name: CH 310N MWF...

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Last Name: First Name: CH 310N MWF 8:00 9:00 (52820) Spring 2006 Dr. Brian M. Bocknack Midterm Exam #2 Thursday, March 23, 2006 7:00–9:00 p.m. Do not open this exam booklet until you are told to do so! This exam is closed book, meaning no books, notes, calculators, or molecular models are allowed. PLEASE WRITE YOUR NAME AT THE TOP OF EACH PAGE !!! Exams written in pencil are not eligible for regrades. Answers written in pencil with ink overlay will not be graded. If you use a pen, only blue or black ink is acceptable. Be prepared to show your valid UT ID card to a proctor when attendance is taken during the exam, and also when you turn in your exam. Page Page Page 2 (16) 8 (32) 14 (20) 3 (16) 9 (16) 15 (20) 4 (12) 10 (15) 16 (20) 5 (06) 11 (15) 17 (20) 6 (15) 12 (20) 7 (32) 13 (25) Total (300) Including this cover page, 3 blank pages (scratch paper), and the last 4 pages, which contain useful spectroscopic data, a periodic table, and pK a values, this exam contains 24 pages. DO ALL QUESTIONS BEST OF LUCK!!!
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Last Name: First Name: 2 1. (Problem worth 32 points; each part worth 4 points) READ THIS QUESTION CAREFULLY!!! In each part below, circle the structure that best answers the question. In each case, there is only one correct answer. (a) This compound would give a positive Tollens test (formation of a silver mirror upon treatment with Ag 2 O + NH 3 OH + H 2 O + EtOH). OH OH O H O O O (b) This compound contains an imine functional group. H 3 C CH 2 N(CH 3 ) 2 H 3 C NH 2 O N CH 3 OO NH 2 (c) This compound cannot be prepared from cyclohexanone using basic reaction conditions (pH > 7). Acidic conditions (pH < 7) must be employed to prepare this compound from cyclohexanone. HO OH HO OCH 3 CH 3 O OCH 3 HO CN O (d) This compound will undergo racemization upon treatment with base. O CH 3 H HO H O CH 2 CH 3 CH 3 O H CH 3 O CH 3 H Problem #1 continues on Page 3… Page Total
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Last Name: First Name: 3 (e) This carboxylic acid will have the lowest pK a value. H 3 C OH O Cl OH O OH O Cl Cl OH O Cl Cl Br OH O Br Br (f) This compound will not undergo decarboxylation (loss of CO 2 ) readily upon heating. O OH O OH O O OH O OH O OH O HO OH O O H OH O O (g) This compound will have the lowest C=O stretching frequency in its IR spectrum OH O O O Na O O O O CH 3 Cl O (h) This compound would be most reactive in a nucleophilic acyl substitution reaction.
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This note was uploaded on 05/02/2011 for the course CH 310 N taught by Professor Blocknack during the Spring '08 term at University of Texas.

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2006MidtermExam#2 - Last Name: First Name: CH 310N MWF...

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