Assign 6-4 - 2. CH 3-C CH 3 CH 3 Br This is fastest in E1...

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Problem Set 6-4 1. Indicate the most reactive substrate in E2 reactions 2. Indicate the most reactive substrate in E1 reactions 3. Write the mechanism of each of the following reactions. If a mechanism is two or more steps, indicate which step is the slow step. A. CH 3 -CH-CH 3 I + KOH(alcohol) heat B. CH 3 -C CH 3 CH 3 Br alcohol, heat CH 3 -CH CH 2 CH 2 C CH 3 CH 3 + H 2 O + I - + H + Br - + con H 2 SO 4 heat + H 2 O OH .. .. C. 4. Which of the following alkenes is the most stable (lowest energy) ? CH 2 CH 3 CH 2 CH 3 CH 3 CH 2 CH 3 CH 3 -CH 2 A. B. C. D. CH 3 CH 2 CH 2 Cl CH 3 C CH 3 CH 3 Cl CH 3 CH CH 3 Cl CH 3 CH 2 CH 2 Br CH 3 C CH 3 CH 3 Br CH 3 CH CH 3 Br
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ANSWERS 1. CH 3 -C CH 3 CH 3 Cl E2 is one-step mechanism; reaction is driven by product (alkene) stability. The product of its reaction, CH 2 C CH 3 CH 3 , is the most stable of the alkenes formed
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Unformatted text preview: 2. CH 3-C CH 3 CH 3 Br This is fastest in E1 reactions because it forms the most stable most easily formed carbocation (3 o carbocation). in the slow step of the mechanism. CH 3-C CH 3 CH 3 Br slow CH 3-C CH 3 CH 3 + Br 3. . A. CH 3-CH I CH 3-CH CH 2 H 2 O I -O .. : .. H CH 2 H E2 CH 3-C CH 3 CH 3 Br slow CH 3-C CH 3 CH 3 + Br CH 3-C CH 3 CH 2 H C CH 3 CH 2 CH 3 H + B. ( E1 ) 3 (cont) OH .. .. H + OH 2 .. .. OH 2 .. .. H + + H + C. slow 4. CH 2 CH 3 CH 3 C. This alkene has the greatest number of alkyl substituents on alkene carbons; this makes it the most stable...
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This note was uploaded on 04/07/2009 for the course CHE 311 taught by Professor Drake during the Fall '08 term at American International.

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Assign 6-4 - 2. CH 3-C CH 3 CH 3 Br This is fastest in E1...

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