Mr Tall
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#1
Report Thread starter 7 years ago
#1
why is CH3CH(OH)CN not an alcohol? surely it is as it has an hydroxyl group?

Apparently it's called 2-hydroxypropanenitrile, but, why isn't called propanenitrile-2-ol?

thanks
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anatomical frog
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#2
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The CN group takes priority over the OH group, hence you use hydroxyl- as opposed as -ol. That's just the IUPAC rules I guess.

[Edit: This is because as the CN is the priority, it goes on the end of the name as the suffix (i.e: -nitrile is used on the end to show the CN group.]
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Sparta_Kane
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#3
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Yes, it does have an alcohol functional group. I think it's naming conventions. Normally the "most important" functional group is named last, and in this case it is the -CN group.
Also might be that since alcohols can also have the prefix "hydroxy-" as well as the "-ol" suffix it works. Maybe the -CN group doesnt have a prefix version so it is left as a "-nitrile"
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anatomical frog
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#4
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(Original post by Sparta_Kane)
Yes, it does have an alcohol functional group. I think it's naming conventions. Normally the "most important" functional group is named last, and in this case it is the -CN group.
Also might be that since alcohols can also have the prefix "hydroxy-" as well as the "-ol" suffix it works. Maybe the -CN group doesnt have a prefix version so it is left as a "-nitrile"
The prefix for CN is cyano- I believe. But you're right about the functional groups.
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Mr Tall
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#5
Report Thread starter 7 years ago
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(Original post by anatomical frog)
The CN group takes priority over the OH group, hence you use hydroxyl- as opposed as -ol. That's just the IUPAC rules I guess.
why does it take priority?

many thanks.
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anatomical frog
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#6
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(Original post by Mr Tall)
why does it take priority?

many thanks.
The IUPAC sets an order of groups, to make naming universal. Unfortunately I can't remember the exact order, but CN is higher than OH.

The exception to the rule is with an alkene, this always ends in -ene (of the compounds you study at A level)

[Edit: Here's a complete list. http://www.masterorganicchemistry.co...nomenclature/]
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Mr Tall
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#7
Report Thread starter 7 years ago
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(Original post by anatomical frog)
The IUPAC sets an order of groups, to make naming universal. Unfortunately I can't remember the exact order, but CN is higher than OH.

The exception to the rule is with an alkene, this always ends in -ene.
ok thanks buddy
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