2OA3 - Test 2 Solutions

2OA3 - Test 2 Solutions - NAME Lab Station Please circle...

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NAME:________________________________ Student No.__________________ Lab Station: __________________ Please circle your lab section. Tuesday Wednesday Thursday Friday L01 L02 L03 L04 CHEM 2OA3 TEST #2 May 24, 2007 6:00 PM Duration: 120 minutes Total: 90 Marks This test contains 11 pages and 8 questions. Answer NEATLY in the space provided. It is YOUR responsibility to ensure that your answers are legible. Answers written in pencil WILL NOT be remarked. Molecular models are permitted. For marker’s use only: Question: 1 2 3 4 5 6 7 8 Total Out of: 10 13 10 8 13 5 10 21 90 Mark: 1
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[10] 1. Draw a complete mechanism, including all appropriate arrows, for the following reaction. Note the major product and explain your reasoning. OH O H H O + H H H H H O H O + H H H O H H O H O + H H H O H O H O H H O + H H H O + H H H 2 O (a) + H 2 SO 4 + + + + + + + + + major - more stable carbocation intermediate (1) (1) (1) (1) (1.5) (0.5) (0.5) (0.5) (0.5) (0.5) (0.5) (0.5) (0.5) (0.5) 2
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[13] 2. Because of their high-potency, low-mammalian toxicity, and photostability, certain esters of halovinylcyclopranecarboxilic acids (pyrethroids) are promising insecticides. An important precursor to this class of insecticides is the carboxylic acid 2 prepared as follows: Copper(I) chloride (CuCl) is a catalyst in this reaction and is known to abstract a chlorine atom from F 3 CCCl 3 to generate a radical and Cu(II)Cl 2 . With this in mind, propose a reasonable mechanism, including all appropriate arrows, for the synthesis of compound 1 using the reagents listed.
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2OA3 - Test 2 Solutions - NAME Lab Station Please circle...

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