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Topic: substitution in cyclohexane  (Read 1858 times)

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Offline lovekblue

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substitution in cyclohexane
« on: December 13, 2013, 02:46:55 PM »
See attached picture.
The answer is B. Please draw out the mechanism of it. There should be ring flip since the Cl is in the equatorial position but nucleophile can only attack when the leaving group is in the axial position? Tho when I try it out with ring flips and nucleophile attack and causes a inversion (SN2), I got back an axial group while the answer is in the equatorial.
Please help, thanks

Offline lovekblue

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Re: substitution in cyclohexane
« Reply #1 on: December 13, 2013, 02:48:58 PM »
Also have a second question.

Why is D considered as non conjugated while E is conjugated?
Thanks again.

Offline zsinger

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Re: substitution in cyclohexane
« Reply #2 on: December 13, 2013, 05:03:13 PM »
E is exactly one position away from another double bond-therefore contributing resonance.  The other position is not quite so close to a DB-->therefore, no resonance :).    I think :)
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

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