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Topic: Quick question about naming with aromatic compounds  (Read 2946 times)

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Offline psychoNOT

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Quick question about naming with aromatic compounds
« on: November 19, 2011, 11:18:07 PM »
Here is a structure:


My answer guide says the correct name is 3-phenyl-1-butanol.

I had written sec-butan-4-olbenzene.  Is this completely wrong?  The rules say that benzene is used as the root unless a carbon substituent is > or = 6 C long, butanol is 4.  Does an alcohol just negate this general rule?  I know with alkanes the C bonded to an OH should have the lowest number, but this compound also contains a benzene.

I can see the ambiguity with using sec-butanol - the OH should have the lowest number, so it should be called sec-butan-1-ol, but that wouldn't specify whether the OH was on the carbon on the left or right side of the butane substituent, so I guess I understand that this isn't correct, but I'm not entirely sure what specific rule in terms of nomenclature makes this name incorrect.  Any hints or help are appreciated!

Thank you
psycho

Offline psychoNOT

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Re: Quick question about naming with aromatic compounds
« Reply #1 on: November 20, 2011, 02:23:34 AM »
Follow up (semi-related)

Can you use the para/ortho/meta terminology for cycloalkenes?

e.g. p-hydroxycyclohex-2-enone?  Or does it have to be 4-hydroxycyclohex-2-enone?

Thank you

Offline Telamond

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Re: Quick question about naming with aromatic compounds
« Reply #2 on: November 20, 2011, 03:37:12 AM »
Benzene substituents to these are usually referred to as phenyl.

Your answer, sec-butan-4-olbenzene doesn't really tell the placement of the phenyl group relative to the alcohol.

For your follow-up question, para/ortho/meta terminology only works for arenes (aromatic hydrocarbons like benzene etc).
http://en.wikipedia.org/wiki/Arene_substitution_patterns

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