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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: pathos6296 on April 13, 2012, 12:38:37 AM

Title: Fastest epoxide forming cyclic compound.
Post by: pathos6296 on April 13, 2012, 12:38:37 AM

The compound in question is 1-chloro-4-isopropyl-3-cyclohexanol: I know that iso-p group is in an equatorial lock. My question is, under basic conditions (which would mean the hydroxyl group would be deprotonated an undergo Sn2 substitution on the chloro group to form an epoxide), which relationship between the chloro and hydroxyl group should exist for an efficient epoxide forming process? Cis, or trans?
Attached is a poorly drawn picture for reference.

Title: Re: Fastest epoxide forming cyclic compound.
Post by: pathos6296 on April 13, 2012, 12:47:59 AM

My bad, 1 chloro-4-isopropyl-2cyclohexanol*

Title: Re: Fastest epoxide forming cyclic compound.
Post by: discodermolide on April 13, 2012, 02:01:52 AM

Quote from: pathos6296 on April 13, 2012, 12:47:59 AM

My bad, 1 chloro-4-isopropyl-2cyclohexanol*

They should be trans and antiperiplanar to one another. In this case you should get the compound I drew.

Title: Re: Fastest epoxide forming cyclic compound.
Post by: pathos6296 on April 13, 2012, 02:13:53 AM

Quote from: discodermolide on April 13, 2012, 02:01:52 AM

Quote from: pathos6296 on April 13, 2012, 12:47:59 AM

My bad, 1 chloro-4-isopropyl-2cyclohexanol*

They should be trans and antiperiplanar to one another. In this case you should get the compound I drew.

So, like this then?

Title: Re: Fastest epoxide forming cyclic compound.
Post by: discodermolide on April 13, 2012, 02:19:21 AM

yes