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Why is this? AS Level Chemistry

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 :smile:
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.]
(edited 10 years ago)
Reply 2
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"
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.
Reply 4
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.
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.com/2011/02/14/table-of-functional-group-priorities-for-nomenclature/]
(edited 10 years ago)
Reply 6
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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