Examination%20_1%20Spr%202008

Examination%20_1%20Spr%202008 - Spring2008...

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CHEM 235 – Organic Chemistry II Spring 2008 Mid Term Examination #1 Feb. 8 th , 2008 This examination is worth 100 points out of a possible total of 700 points for this course, and consists of 8 questions. You are required to answer all questions, but are not necessarily required to answer all parts of a given question, so read the questions carefully. In cases where you are not required to answer all parts, indicate clearly which parts you wish to have graded. Otherwise, I will grade the fist answers I see. Question 1 (15 points) Provide systematic names for three of the following five compounds. O 2 N Cl Br CH 3 Br Br OH NH 2 Cl
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Question 2 (12 points). Predict, with reference to the relevant reaction mechanism, the outcome of the following reaction (including stereo and regiochemical outcomes). You must include the detailed reaction mechanism in your answer, and may include other structures or diagrams to explain your answer. NBS, h ν CCl 4
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Question 3 (10 points). Explain why 1,3 cyclopentadiene has a pK a of only 16, whereas 1,3,5 cycloheptatriene has a pK a of above 40. H H pK a > 40 H H pK a = 16 Question 4 (8 points). Indicate which of the following compounds are aromatic. N N N H O N O O O BF 4
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Question 5 (12 points). Predict, with reference to the relevant reaction mechanism, the outcome of the following reaction (including stereo and regiochemical outcomes). You must include the detailed reaction mechanism in your answer, and may include other structures or diagrams to explain your answer. C N Cl 2 FeCl 3
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Question 6 (12 points). Predict, with reference to the relevant reaction mechanism, the outcome of the following reaction (including stereo and regiochemical outcomes). You must include the detailed reaction mechanism in your answer, and may include other structures or diagrams to explain your answer. OCH 3 HNO 3 /H 2 SO 4
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Question 7 (21 points). Predict the outcome of seven of the following ten reactions, including any stereochemical or regiochemical outcomes. Br 2 , h ν NBS, AIBN CCl 4 , 1) NaNH 2 /NH 3 2) I NO 2 HNO 3 /H 2 SO 4 + Cl O AlCl 3 OCH 3 SO 3 /H 2 SO 4 CH 3 NO 2 SnCl 2 /HCl OCH 3 CH 3 Cl 2 FeCl 3 + CHCl 3 KOH OCH 3 + Br AlCl 3
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Question 8 (10 points). Provide structures for two of the following three names p chloronitrobenzene 1,3,5 trimethyl
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Examination%20_1%20Spr%202008 - Spring2008...

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