2006FinalExamAnswers - Last Name: First Name: MWF 8:009:00...

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DO ALL QUESTIONS!!! BEST OF LUCK!!! Last Name: First Name: CH 310N MWF 8:00–9:00 (52820) Spring 2006 Dr. Brian M. Bocknack Final Examination – Answer Key Tuesday, May 16, 2006 2:00–5:00 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 !!! No regrades are possible for this exam, so you may feel free to use pencil. If you do use a pen, only blue or black ink is acceptable. Answers written in red ink will not be graded. Be prepared to show your valid UT ID card to a proctor when attendance is taken, and also when you turn in your exam. You may not leave the exam room for any reason until you turn in your exam. Once you turn in your exam and leave the exam room, you will not be allowed to return!!! Page Page Page 2 (25) 9 (15) 16 (20) 3 (25) 10 (30) 17 (20) 4 (10) 11 (32) 18 (20) 5 (20) 12 (32) 19 (20) 6 (10) 13 (16) 20 (30) 7 (15) 14 (20) 8 (20) 15 (20) Total (400) Including this cover page, 3 blank pages (scratch paper), and the last 3 pages, which contain useful spectroscopic data, a periodic table, and a table of pK a values, this exam contains 26 pages. Please feel free to tear off the scratch paper and the periodic table to use as you work through the exam
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Last Name: First Name: 2 1. (Problem worth 50 points; each part worth 5 points) PLEASE READ THIS QUESTION VERY CAREFULLY !!! In each part below, circle the structure that best answers the question. In each case, there is only one possible correct answer! (a) Which compound will produce a 1 H NMR spectrum that does not contain a signal that is split into a triplet (3 lines)? O O O O O O Cl (b) Which compound will have the fewest number of resonances in its 13 C NMR spectrum? (c) Which cation is most stable due to its aromaticity ? (d) Which compound would be most reactive in an electrophilic aromatic substitution reaction? Br C OCH 3 OH N O (e) Which diene will be unreactive in a Diels–Alder reaction with a dienophile because it cannot adopt the reactive s- cis conformation? H 3 C H 3 C O O OCH 3 OCH 3 Problem #1 continues on Page 3… Page Total
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First Name: 3 (f) Which structure represents a 2° amide ? N H NH 2 N CH 3 N H O N H 3 C CH 3 (g) Which structure contains a hemiacetal ? O HO HO OH OCH 3 OH S OCH 3 NC OH O OH H 3 C OH O (h) Which carbonyl compound will be least reactive toward attack by a nucleophile? N O OCH 3 O OH O Cl O O O CH 3 CH 3 CH 3 O (i) Which compound will not undergo decarboxylation (loss of CO 2 ) upon gentle heating? O OH O O OH HO O O O CH 3 O OH OH O OH HO O O O (j) Which compound will give a positive Tollens’ test (formation of a silver mirror upon treatment with Ag 2 O, NH 4 OH, EtOH, H 2 O)? O
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2006FinalExamAnswers - Last Name: First Name: MWF 8:009:00...

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