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Sp11_HW10 KEY - Sessler CH310M/318M Homework Problem Set 10...

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Sessler CH310M/318M Homework Problem Set 10 Due Friday April, 29th 2011 1 Circle the section in which you are enrolled: 310M 318M Please write the first three letters of your last name in the above boxes Name:_______________________________ UT EID:_____________________________ Signature:____________________________ Grade ( + / - / 0 ):______________________ K E Y
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Sessler CH310M/318M Homework Problem Set 10 Due Friday April, 29th 2011 2 1. Draw structural formulas for the products formed when each compound is heated at reflux in concentrated HI. a. b. c. d.
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Sessler CH310M/318M Homework Problem Set 10 Due Friday April, 29th 2011 3 2. Show reagents to convert cyclohexene to each of the following compounds. a. OsO 4 b. HIO 4 c. NBS, h ν or Δ d. NaOH e. PCC or H 2 CrO 4 f. MCPBA g. H + / H 2 O or OH - / H 2 O h. MeONa / MeOH i. PCC or H 2 CrO 4 j. NH 3 k. 1. 2. H + / H 2 O l. 1. KCN 2. H + / H 2 O m. LiAlH 4 or H 2 / Pd / C
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Sessler CH310M/318M Homework Problem Set 10 Due Friday April, 29th 2011 4 3. Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in the synthetic scheme shown below. Be sure to use curved arrows to show the flow of electrons and show all lone pairs.
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