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Topic: Just a few questions on stereo-chemistry nomenclature  (Read 2440 times)

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Offline pledge

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Just a few questions on stereo-chemistry nomenclature
« on: September 15, 2011, 10:20:56 PM »
http://i.imgur.com/H4Uu1.png <-- here are the specific problems that are tripping me up with my best attempts

When naming a cyclo-alcohol like these, how do you decide which to make the "1-carbon?"

I thought if there was only two bonds/it could go either way when counting you go alphabetically when assigning numbers but when you name the molecule, what letter does the OH group get? Hope that's clear, this is my first post but this forum seems like a great resource.

Thanks for your help and time!

Offline Dan

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Re: Just a few questions on stereo-chemistry nomenclature
« Reply #1 on: September 16, 2011, 03:37:34 AM »
The structures are named after the parent alcohols - in these cases either cyclohexanol or cycloheptanol. Carbon 1 (C1) is the carbon bonded to the alcohol.

Let's take your fluorinated compound as the example. The parent compound is cyclohexanol, but we have F on the carbon adjacent to C1. The carbon adjacent to C1 is C2, so the F is on C2.

The systematic name would be (1R,2R)-2-Fluorocyclohexanol. Note that the position of the alcohol (1) is implicit, it does not need to be stated.

The numbering you have assigned to the other two structures is all over the place and not even self consistent. Eg. (1S,3R)-1-bromo-4-cyclohexanol - this name implies stereogenic centres at C1 and C3, but substituents at C1 and C4. There is a similar problem for (1S,2R)-4-methyl-1-cycloheptanol.
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