310MSp06MidtermExam3

310MSp06MidtermExam3 - Last Name First Name TTh...

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Last Name: First Name: CH 310M/318M TTh 8:00 9:30 (52810/53030) Spring 2006 Dr. Brian M. Bocknack Midterm Exam #3 Wednesday, April 19, 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. 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. Page Page Page 2 (12) 8 (30) 14 (25) 3 (16) 9 (30) 15 (25) 4 (12) 10 (20) 5 (20) 11 (20) 6 (25) 12 (20) 7 (20) 13 (25) Total (300) Including this cover page, 2 blank pages (scratch paper), and the last page, which contains a periodic table (including electronegativity values), this exam contains 18 pages. DO ALL QUESTIONS BEST OF LUCK!!!
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Last Name: First Name: 2 1. (Problem worth 40 points; each part worth 4 points) READ THIS QUESTION CAREFULLY!!! In each part below, choose the best answer. Write the letter that corresponds to your choice in the box. There should only be one letter in each box. In each part of this question, there is only one choice that is “best”! Please refer to the carbocation structures shown below to answer the questions in Parts (a) through (c). CH 3 CH 3 CH 3 CH 2 A B C D (a) Which carbocation shown above would be most stable ? (b) Two of the carbocations shown above will yield a more stable 3° carbocation upon rearrangement via a hydride shift . Write the letter corresponding to the less stable of these carbocations in the box below. Be sure to write only one letter in the box !!! (c) One of the carbocations shown above will yield the carbocation shown below upon rearrangement via an alkyl shift . Write the letter corresponding to this carbocation in the box below. Problem #1 continues on Page 3… Page Total
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First Name: 3 Please refer to the radical structures shown below to answer the questions in Parts (d) and (e). A B C D CH 2 CH 3 C CH 3 CH 3 C C CH 3 CH 3 CH 2 H CH 3 C CH 3 H C H CH 3 C C CH 3 CH 3 CH 3 CH 3 C CH 2 H CH 2 CH 3 E (d) Which radical shown above would be least stable ? (e) Which radical structure shown above is one contributing resonance structure of a resonance hybrid ? (f) Which alkyl bromide shown below will not react with an acetylide anion in a reaction which forms a new carbon–carbon bond? (g) 3,3-Dimethylpentane (structure shown below) undergoes radical chlorination with Cl 2 in the presence of light. Including stereoisomers , how many different monochlorinated substitution products will form? 3,3-Dimethylpentane
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310MSp06MidtermExam3 - Last Name First Name TTh...

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