3580 Spring 2011_PSET 7 - benzene ring. Cl AlCl 3 OH ? (4)...

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Chemistry 3580 Spring 2011 Prof. William Dichtel Homework: Problem Set #7 These problems are representative of the difficulty level of Prelim #2. They do not cover the material that will be tested comprehensively. (1) The compound below is named Pentalenene. What type of terpene is it? Circle its isoprenoid units. H Pentalenene (2) Pentalenene can be synthesized from a different terpene, humulene, under acidic conditions. Draw a rational arrow pushing mechanism for this transformation. H Pentalenene Humulene Enzyme (in nature) or cat. H + (3) The Friedel-Crafts alkylation has problems that limit its applicability. Explain what problems might be encountered in the reaction given below. Next, using the phenol derivative shown below, design a high yielding synthesis of the desired alkyl-substituted
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Unformatted text preview: benzene ring. Cl AlCl 3 OH ? (4) Explain the following peaks in the electron impact mass spectrum of the following compound. Draw an arrow pushing mechanism for each. O Chemical Formula: C 12 H 16 O Exact Mass: 176.12 EI-MS Explain m/z peaks at 148, 120, and 86. (5) For each of the following pairs of compounds, choose the compound likely to have the HIGHER equilibrium constant for hydration of its carbonyl. O vs O O H O vs O O O vs O O O H O CN NC H O vs (6) Predict the aromatic products of the following oxidation reactions. HO HO MnO 2 HO HO CrO 3 vigorous (7) Synthesize the following products from the given starting material. No synthesis should require more than 5 steps. OH Br O NC HO I O OH...
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3580 Spring 2011_PSET 7 - benzene ring. Cl AlCl 3 OH ? (4)...

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