Exam3.2005

Exam3.2005 - CHM 212 Name Examination 3 April 25, 2005 1....

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Unformatted text preview: CHM 212 Name Examination 3 April 25, 2005 1. [30 points] (a) Provide a detailed, step—by-step mechanism that accounts for the formation of the product in the following reaction. The mechanism must include the formation of the electrophile and account for the substitution pattern. ‘ (b) A minor product (mp 85 °C) has the formula C8H6N205. Provide its structure a_n_d explain Why it is only a minor product. 0 _ O . OZN HNO3, st04 --—--—> 100 °C 2. [30] Give the structural formula for the major product of each reaction. Clearly show any relevant stereochemistry. \ H202, CF3SO3H ————-—> CN 150 °C 0 y: \NQ Brz in glacial CHaCOZH I ——-————-———> H 25 °C H2 CO HNOZ, HCl(aq) —————-——> Br 0 0c 1) excess CH3I NH2 2) AgZO, H20 OLCH3 3) 150°C ——"——> F F No2 _.d. + NHZNHO flL, '” 100°C N09 CHZNHZ CH9 Clo + CH9CH7B1' ——————-——> ~ ~ 20 °C 3. [20] 3-bromocyclopropene reacts readily with silver tetrafluoroborate (AgBF4) to yield silver bromide and an organic product with a single 1I-l—NMR signal at 11.0 5, but 5—bromocyclopentadiene does not react With silver tetrafluoroborate under the same conditions. (a) Using appropriate terminology, structures and diagrams explain the differences in reactivity for these two bromo- compounds. (b) How does the spectral evidence support the conclusion? 4. [20] Starting with benzene provide a reas nable synthesis for the preparation of either 3-bromo—4=—nitrosoacetanilide or 1, —dibromobenzenesulfonic acid. Any chemicals necessary for the synthesis may be used but the aromatic ring must originate with benzene. Do not provide a synthesis for both compounds. If two answers are given the less correct answer will be included in the 0% rading. ...
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This test prep was uploaded on 04/20/2008 for the course CHM 212 taught by Professor Thomsen during the Spring '08 term at F & M.

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Exam3.2005 - CHM 212 Name Examination 3 April 25, 2005 1....

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