1aa3-2012-tut9-a

1aa3-2012-tut9-a - CHEMISTRY 1AA3 Week of TUTORIAL PROBLEM SET 9 Solutions 1 Circle the higher priority groups on each of the alkene carbons and

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CHEMISTRY 1AA3 Week of March 12, 2012 TUTORIAL PROBLEM SET 9 – Solutions ______________________________________________________________________________ Page 1 of 4 1. Circle the higher priority groups on each of the alkene carbons, and identify the following alkenes as E or Z, and. Name the first two compounds. Solution: Br Cl Cl F Z -4-isopropyl-3,5-dimethyl-3-heptene E -1-bromo-1,2-dichloro-2-fluoro-ethene F NH O Cl Cl C H 3 E -isomer Z -isomer Top alkene carbon: travelling clockwise around the methylcyclopentane gets you to a tertiary carbon faster than going either way around the cyclohexane ring. Bottom alkene carbon: clockwise gets you to Cl, which has priority over CH 3. 2. Show the mechanism of addition of HCl to cyclohexene. Use curly double-barbed arrows to indicate the movement of electrons from nucleophiles to electophiles. Indicate the polarity of HCl using + and - symbols. Solution: H Cl H + Cl - Cl   
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2 3. Show the major product(s) obtained by reaction of excess hydrogen bromide with: a. 3-ethyl-2-pentene
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This document was uploaded on 03/29/2012.

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1aa3-2012-tut9-a - CHEMISTRY 1AA3 Week of TUTORIAL PROBLEM SET 9 Solutions 1 Circle the higher priority groups on each of the alkene carbons and

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