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Topic: Substituted acohol - nomenclature probem  (Read 2158 times)

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Offline Giorgio123321

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Substituted acohol - nomenclature probem
« on: February 24, 2017, 06:52:06 AM »
Hello,

I had to give a name to this molecule and I don't know which carbon chain to take as the main one.



I thought that there were mainly 2 cases : One in which I took the cyclohexane chain as main and one in which I took the Substituted  pentane one.

Wouldn't the main one be the smaller one containing the hydroxil groups?

So, is  1-ciclohexyl-3-chloride-1,5-pentandiol ? Or is the cyclic structure more important?

Please if you answer,  link a reliable source to present as a "back up"  to eventually give to my professor.

Thank you.

Offline Dan

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Re: Substituted acohol - nomenclature probem
« Reply #1 on: February 24, 2017, 08:29:32 AM »
So, is  1-ciclohexyl-3-chloride-1,5-pentandiol ?

No, 1-cyclohexyl-2-chloro-1,5-pentanediol would be:

C1CCCCC1C(O)C(Cl)CCCO

I look at it this way - you either name it as a cyclophexyl-substituted pentanol or a pentyl-substituted cyclohexanol.

How do you think we can decide whether cyclohexanol or pentanol have priority?
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Offline Giorgio123321

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Re: Substituted acohol - nomenclature probem
« Reply #2 on: February 24, 2017, 09:34:00 AM »
No ok, you're right about the picture.

I had problem in using the online editor and drew it wrong.

Given the picture you posted, does it correspond to the name I wrote?

I don't see how it can possibly be a cyclohexanol if the OH's aren't on the cyclic chain?


Offline Dan

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Re: Substituted acohol - nomenclature probem
« Reply #3 on: February 24, 2017, 09:46:00 AM »
Given the picture you posted, does it correspond to the name I wrote?

Yes, the picture I posted corresponds to the name you wrote.
The name you wrote does not match the picture you posted.
I am assuming you posted the correct picture, but got the name wrong.

Quote
I don't see how it can possibly be a cyclohexanol if the OH's aren't on the cyclic chain?

In the picture you posted, there is an alcohol on the cyclohexane ring, you posted this:

C1CCCCC1(O)C(Cl)CCC(O)

There are two ways you could name it (but only one is correct) based on either:

1. Cyclohexylbutanol   [note: I said cyclohexylpentanol before, this was a mistake]
2. Butylcyclohexanol   [note: I said pentylcyclohexanol before, this was a mistake]

What you need to decide is whether butanol or cyclohexanol has a higher priority to choose the parent compound for naming. What do you think?
My research: Google Scholar and Researchgate

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