1-Chloro-4-isopropylcyclohexane exists as two stereoisomers: one cis and one trans. Treatment of either isomer with sodium ethoxide in ethanol gives 4-isopropylcyclohexene by an E2 reaction. CH,CH,O Na* CI CH,CH,OH 1-Chloro-4- 4-Isopropylcyclohexene isopropylcyclohexane The cis isomer undergoes E2 reaction several orders of magnitude faster than the trans isomer. How do you account for this experimental observation?

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1-Chloro-4-isopropylcyclohexane exists as two stereoisomers: one cis and
one trans. Treatment of either isomer with sodium ethoxide in ethanol gives
4-isopropylcyclohexene by an E2 reaction.
CH,CH,O Na*
CI
CH,CH,OH
1-Chloro-4-
4-Isopropylcyclohexene
isopropylcyclohexane
The cis isomer undergoes E2 reaction several orders of magnitude faster than
the trans isomer. How do you account for this experimental observation?
Transcribed Image Text:1-Chloro-4-isopropylcyclohexane exists as two stereoisomers: one cis and one trans. Treatment of either isomer with sodium ethoxide in ethanol gives 4-isopropylcyclohexene by an E2 reaction. CH,CH,O Na* CI CH,CH,OH 1-Chloro-4- 4-Isopropylcyclohexene isopropylcyclohexane The cis isomer undergoes E2 reaction several orders of magnitude faster than the trans isomer. How do you account for this experimental observation?
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