Quiz2A - 1 CHM 2123, Quiz #2: Free radical induced...

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1 CHM 2123, Quiz #2: Free radical induced isomerization of an alkene. Electrophilic Addition to an alkene Assigned: September 21st 2006 Due: September 25 2006, before 5pm MARKING SCHEME 1. a) The conversion of dimethyl fumarate to dimethyl maleate cannot be performed in less than a day if it is kept in the dark at room temperature. Why? (1 point) The radical-induced isomerization requires the presence of Br• radicals. In the absence of light or heat, there are hardly any (or no) Br• radicals present in solution and the reaction is therefore slow… b) Which reaction(s) could happen if we left the same reaction mixture for 6 months in the absence of light? Use chemical equation(s) to explain your answer. (2 points) Six months is a long reaction time. There are two possibilities: 1) Radical-induced isomerization of dimethyl fumarate to dimethyl maleate H 3 CO 2 C CO 2 CH 3 H H H H 3 CO 2 C CO 2 CH 3 H Br 2 (via Br•) 2) Electrophilic dibromination of dimethyl fumarate (even though the alkene is electron-
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Quiz2A - 1 CHM 2123, Quiz #2: Free radical induced...

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