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Topic: Why? Organic chemistry - naming alchohols  (Read 2793 times)

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Offline kensher

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Why? Organic chemistry - naming alchohols
« on: July 18, 2016, 06:09:43 PM »
Hi.

I'm having a task that I struggle with in my chemistry book. The task is naming the alchohol.
I get presented with this following structural formula (see attachment).

The right answer is: 2-ethylbutane-1-ol (I thought it would be 3-methylpentane-3-ol).
The reason the book gives (which makes no sense to me): "The C-atom, which the OH-group is bonded to, should be considered a part of longest coherent carbon chain".

Can somebody please explain this?

Thanks in advance.




Offline AWK

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Re: Why? Organic chemistry - naming alchohols
« Reply #1 on: July 18, 2016, 07:40:25 PM »
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Offline Arkcon

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Re: Why? Organic chemistry - naming alchohols
« Reply #2 on: July 18, 2016, 07:56:38 PM »
The reason the book gives (which makes no sense to me): "The C-atom, which the OH-group is bonded to, should be considered a part of longest coherent carbon chain"

Read it carefully. The C-atom, with the OH is the longest one.  That, in at least this case, forces the name to be -1-ol, not -3-ol.  Can you redraw this picture to highlight that?  Remember, right angle bends in a aliphatic chain are tofit it on the page, they don't mean anything when naming the molecule.
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline Dan

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Re: Why? Organic chemistry - naming alchohols
« Reply #3 on: July 19, 2016, 02:29:02 AM »
The right answer is: 2-ethylbutane-1-ol (I thought it would be 3-methylpentane-3-ol).

3-methylpentan-3-ol is this:

CCC(O)(C)CC
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Offline kensher

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Re: Why? Organic chemistry - naming alchohols
« Reply #4 on: July 19, 2016, 12:42:37 PM »
The reason the book gives (which makes no sense to me): "The C-atom, which the OH-group is bonded to, should be considered a part of longest coherent carbon chain"

Read it carefully. The C-atom, with the OH is the longest one.  That, in at least this case, forces the name to be -1-ol, not -3-ol.  Can you redraw this picture to highlight that?  Remember, right angle bends in a aliphatic chain are tofit it on the page, they don't mean anything when naming the molecule.

Thank you!
Your answer explained it. The short chain becomes the «long» chain because it has OH-attached to it. Thanks.

Offline AWK

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