Exam3.2003

Exam3.2003 - H“ i CHM 212 Name [email protected] 1[25...

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Unformatted text preview: H“ i CHM 212 Name Examination @3 April 28, 20.03 1. [25 points] (a) Provide a detailed, Step-by—step mechanism that accounts for the formation of the products in the following reaction. (13) Why is the reaction best performed With an excess of benzene? CH3CH2CH2CH2BL 80 °C 2. [20] For each question circle the best answer. The aromatic compomid: ' O / Q Q \ / The LUMO for 1,3—butadiene: The least basic compound: NH2 ©NOZ 0/ CH2NH2 CH3 The deactivating, meta—directing group in electrophilic aromatic substitution: -CF3 -NH2 ~NO The diene that will be most reactive in a Diels—Alder reaction: UGO/fl 3. [20] Provide the structural formula for the maj or product of each reaction. Clearly show any relevant stereochernistry. 1) excess CH3I NH2 2) AgZO, I-IZO OLCH3 3) 150 0c: O | I C\N.© HNOg, H2504 I —--—-———'—‘+ H 50 °C NH2 GE HNOQ, HCl(aq) Br ' 0°C Br Br N02 + NHONHZ pyrldlne ‘ 100 °C NO 2 CH3 200 °C ————————> CH3 4. [20] 1,3—cyclobutadiene may be isolated only at very low temperatures (e. g., 10 K). Attempts to prepare this compound at higher temperatures yield a stable compound (CgHs) as a major product. (a) Is 1,3—cyclobutadiene aromatic or anti—aromatic? Use a qualitative molecular orbital energy level diagram to support the answer. b) Could 1H—N1VIR be used to test your conclusion stated in part a? Explain. c) What is the structure of the CgHs compound? (:1) Give an appropriate mechanism for the thermal reaction that produces Cal-lg . 5. [15] Starting with benzene provide a reasonable synthesis for the preparation of either 3—bromo—N,N—dirnethy1aniline or 1,3-dibromobenzene. Do not provide withesis for both compounds. Any chemicals necessary for the synthesis may be used but the aromatic ring must originate with benzene. ...
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Exam3.2003 - H“ i CHM 212 Name [email protected] 1[25...

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