Friday_Session_2 - direction of electron flow. OH O O H 3 O...

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Chem 358 Spring 2009 Friday Session 2 1. (Q4 from Friday Session 1) Suggest a suitable synthesis for each of the following compounds beginning with benzene and suitable organic (containing no more than 4 carbon atoms) and inorganic reagents. O COOH NH 2 (E) (A) (B) (C) (D) (F) 2. (Q7 from Friday Session 1) The insecticide dichlorodiphenyltrichloroethane (DDT) has been made in ton quantities by the reaction shown below. Formulate a detailed stepwise mechanism for the reaction. Use curved arrow formalism to show electron flow. CCl 3 Cl Cl Cl 3 C H O 99% H 2 SO 4 , 15°C, 5 hr Cl DDT 98% + H 2 O 3. Propose a plausible mechanism for the reaction shown below. Use the curved arrow formalism to show the
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Unformatted text preview: direction of electron flow. OH O O H 3 O + 4. Propose a synthesis of the following compounds from benzene. You can disregard the possible formation of minor isomers. SO 3 H NO 2 Cl (a) (b) NO 2 O (c) (d) 5. Treatment of cyclohexene with iodobenzene under the conditions of Heck reaction did not yield 1-phenylcyclohexene but rather yielded exclusively 3-phenylclohexene. Account the these results. + I + Pd(PPH 3 ) 4 Et 3 N 1-Phenylcyclohexene Not formed 3-Phenylcyclohexene Only product Iodobenzene Cyclohexene...
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell University (Engineering School).

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