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A2 Chemistry Nomenclature Amines Strikes Again!

First of all I would like to know why the book has named this (phenylmethyl)amine instead of phenylethylamine? There isn't a CH3 group attached to where does methyl come into it? (see attachment for picture of structure)

Secondly I have problems with this one question which says classify and name CH3NHCH2CH2CH3 as the book says the answer is N-methylpropylamine - secondary, why this name and where did the N come from?
phenylmethylamine.jpg16.9KB
Reply 1
Avatar for Abraxis
Abraxis
It wouldn't be called phenylethylamine as there aren't 2 alkyl groups, only one CH2 = Methyl and NH2 = Amine.

Naming secondary and tertiary amines (as in my text book):
- Identify the longest hydrocarbon chain attached to the nitrogen.
- This with the prefix 'amino' or suffix 'amine' forms the basis for the name.
- Then you identify the alkyl groups attached to the nitrogen and list these at the beginning of the name.
- the prefix N- is used to show that the smaller groups are attached to the nitrogen atom and not the actual carbon chain dealy.

So CH3NHCH2CH2CH3 would be:
- 3 carbon chain = propane = propyl
- amine
- With one alkyl group on the N atom = Methyl
- N- to show the methyl is on the N atom.

N-methylproplyamine.

Hope that helps.
Reply 2
Avatar for Jack Schitt
Jack Schitt
supreme
First of all I would like to know why the book has named this (phenylmethyl)amine instead of phenylethylamine? There isn't a CH3 group attached to where does methyl come into it? (see attachment for picture of structure)

Secondly I have problems with this one question which says classify and name CH3NHCH2CH2CH3 as the book says the answer is N-methylpropylamine - secondary, why this name and where did the N come from?

ethly = 2 carbon

that only had 1 carbon (attached to benzene) => methyl.
Reply 3
Avatar for supreme
supreme
OP
4
Abraxis
It wouldn't be called phenylethylamine as there aren't 2 alkyl groups, only one CH2 = Methyl and NH2 = Amine.

Naming secondary and tertiary amines (as in my text book):
- Identify the longest hydrocarbon chain attached to the nitrogen.
- This with the prefix 'amino' or suffix 'amine' forms the basis for the name.
- Then you identify the alkyl groups attached to the nitrogen and list these at the beginning of the name.
- the prefix N- is used to show that the smaller groups are attached to the nitrogen atom and not the actual carbon chain dealy.

So CH3NHCH2CH2CH3 would be:
- 3 carbon chain = propane = propyl
- amine
- With one alkyl group on the N atom = Methyl
- N- to show the methyl is on the N atom.

N-methylproplyamine.

Hope that helps.


Thanks I can't believe I got confused about meth and eth :redface: . That quote from your textbook was realy helpful as the core text for AQA doesn't actually follow standard nomenclature rules, even though the chef examiner wrote it hmmm...

Anyways :biggrin:

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