2006MidtermExam#3Answers

2006MidtermExam#3Answers - Last Name: First Name: CH 310N...

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Unformatted text preview: Last Name: First Name: CH 310N Spring 2006 Dr. Brian M. Bocknack Midterm Exam #3 Answer Key Thursday, April 20, 2006 7:009:00 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. Questions answered using red ink will not be graded!!! 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 (20) 8 (20) 14 (15) 3 (12) 9 (20) 15 (20) 4 (16) 10 (20) 16 (25) 5 (40) 11 (15) 6 (22) 12 (15) 7 (20) 13 (20) Total (300) Including this cover page, 3 blank pages (scratch paper), and the last page, which contains a periodic table and pK a values, this exam contains 20 pages. DO ALL QUESTIONS BEST OF LUCK!!! 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) Which compound below is an example of a cumulated diene? C (b) Which phenol shown below will be most acidic (i.e. lowest pK a value)? OH OH OH OH OH OCH 3 NO 2 OCH 3 NO 2 (c) Which ester shown below will not undergo a self Claisen condensation reaction? OEt O CH 3 OEt O CH 3 CH 2 OEt O (CH 3 ) 2 CH OEt O O O (d) Which nucleophile listed below will give predominantly 1,2-addition upon reaction with an , -unsaturated ketone? LiAlH 4 (CH 3 CH 2 ) 2 CuLi KCN H 3 C CH 3 O O CH 3 NH 2 (e) Which ether shown below will yield toluene and an alcohol upon reaction with H 2 over a Pd catalyst? O O O O O Problem #1 continues on Page 3 Page Total Last Name: First Name: 3 (f) Which carbonyl compound shown below will yield a methyl ketone upon reaction with (CH 3 ) 2 CuLi, followed by an aqueous workup? O Cl O O O O OH O OEt O NH 2 (g) Which carbonyl compound shown below will yield an aldehyde upon reaction with DIBALH at low temperature, followed by an acidic workup? O Cl O O O O OH O OEt O NH 2 (h) Which C 7 H 8 O isomer below will produce the 1 H NMR spectrum that appears below the structures? OH CH 3 OH CH 3 OH CH 3 OCH 3 OH End Problem #1 Page Total 2H (d) 2H (d) 1H (s) 3H (s) disappears upon D 2 O shake Last Name: First Name: 4 2. (Problem worth 16 points; each part worth 4 points) READ THIS QUESTION CAREFULLY!!! In each part below, a name is given. Draw a structure that corresponds to the name. Write your answer in the appropriate box. the name....
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2006MidtermExam#3Answers - Last Name: First Name: CH 310N...

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