Problem Set IX Key

Problem Set IX Key - Name: K Z, / Chem 343 Spring 2009 TA...

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Unformatted text preview: Name: K Z, / Chem 343 Spring 2009 TA Name: Problem Set 1X Discussion Secition # I. When 3,3,4-trimethyl-2-pentanol is heated in 70% sulfuric acid, 2,3,4—trimethyl-2-pentene is formed as the only product (see below). Write a step-wise mechanism that accounts for the formation of the product. Use curved arrows to show the movement of electron pairs in each step, and draw structure for all intermediates. 0 (7H \ l‘ o~$~a 0 H2804 / A 6 l H 5 PH- l-l GP H \o / \\\§§ //1?1—ww¢+kyl Skipi J II. Show a step-wise synthesis of cis-2,9—dimethyl-5 —decene (structure shown below) Starting with acetylene (ethyne) and alkyl halides with a maximum of 5 carbon atoms. Show one complete reaction for each step. III. For each of the following reactions, provide the additional reactants/reagents (over the arrow) needed to produce the product shown as the major product. The additional reactants/reagents may contain up to four carbon atoms. Ifmore than one step is required, number each step as 1.), 2.), etc. Br OH /\>< H 1 0 ______> Br (C H a): (— 0 a _—______> (c H 3)} cm H CH3 IV. For each of the following reactions, draw the structure of the major product. If the major product is one specific stereoisomer, be sure to show the correct one. If the major product is formed as equal (or approximately equal) amounts of two stereoisomers, clearly indicate which two are formed. I: OCH) / B C OH ‘ 6/ ' \ AX H3 M + ’e "a '1 7L. 0 MC V. \ 5“ I \ 1. N H CH3—CaC—H ) am 2 “we: 2.)CH3CHzBr H CH \ CHso‘ \.,_~ ' c—c'“ H3C\“/ \ CH<CH3>2 '3’ H\ /CH3 \\\\H ' C_C..m (CH3)3O / H3C\“/ \ \ CH<CH3)2 Br Br CH3S' Br : Zl CH3O — 0 “3 CH30H o Y \ ...
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This note was uploaded on 09/15/2009 for the course CHEM 343 taught by Professor Whitlock during the Fall '07 term at Wisconsin.

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Problem Set IX Key - Name: K Z, / Chem 343 Spring 2009 TA...

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