Exam3.2002

Exam3.2002 - CHM 212 3, ’ Name Examination 9 April 24,...

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Unformatted text preview: CHM 212 3, ’ Name Examination 9 April 24, 2002 1. [25 points] (a) Provide a detailed, step-by-step mechanism that accounts for the formation of the product in the following reaction. (b) Why is the reaction best performed with an excess of anisole? (c) Explain the fact that no reaction occurs with the solvent to produce isomeric nitro—t—butylbenzenes. (CH3)3CBr, AlBr3 CH3o’ : CH3O nitrobenzene, 80 °C ..... (. 2. [24] For each question circle the best answer. The most reactive diene in a Diels-Alder reaction with maleic anhydride: OCH3 @0013 N The 1,2-addition product from the reaction of HCl With 1,3-butadiene: N0 N C1 The HOMO for 1,3-butadiene: TM The most basic compound: OCH3 OCH3 NH2 ' ©/NOZ 0/ CHzNHZ CH3 f The compound that Will readily form a polymer by radical, cationic and anionic reaction mechanisms: OA ’ Y The compound that is a polyamide; poly(ethylene terephthalate) poly(methyl methacrylate) nylon 66 3. [21] Provide the structural formula for the major product of each reaction. Clearly show any relevant stereochernistry. V NH2 :1 HNOZ, HCl(aq) Br 0 °c CH2C1 + CH3CH2NH2 —————-—>acet0“e 55 0c 1) excess CH I NH 3 /\)\2 AgZO, H20 3) 150 °C CF 3 $03, H2804 ——————-——>' 85 °C 0 I l C\N.© HNO3, H2504 I ————_——>‘ H 50 °c Br Br - N02 . + NHZNHZ pyrldme 100 °C N02 N+Nc _ CN 150°C 4. [15] Provide a detailed, step-by-step mechanism that accounts for the formation of the product in the following reaction. NaNOZ, HCl(aq) ——————-—-——> N\ 0 °c N\ H NO 5. [15] Starting with benzene provide a reasonable synthesis for the preparation of 3-nitrobenzoic acid or 1,3-dibromobenzene or 3-propy1aniline. Do not provide a synthesis for more than one of these compounds. Any chemicals necessary for the synthesis may be used but the aromatic ring must originate with benzene. \ ...
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Exam3.2002 - CHM 212 3, ’ Name Examination 9 April 24,...

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