Amide vs. Amine

Amine is a Nitrogen on an alkane:

An amine doesnt have a carbonyl group.

An amine doesn’t have a carbonyl group.

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Amide is a Nitrogen with a carboxylic acid:

An Amide. Dont confuse it with an amine.

An Amide. Don’t confuse it with an amine.

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Oh you’re still confused?

  • An amine is usually taught in first semester chemistry
  • An amide is introduced to you after your teacher has already shown you a carbonyl group, and then later your teacher will start getting into proteins. This is all in the second year of O-chem
  • Carbonyl groups are hella important for the MCAT and for learning the structure of proteins, amino acids, and polypeptides. If you don’t know what any of that means, then you’re probably looking at an amine
  • An amine can be written like this:   R-NH2, or CH3-CH2-CH2-NH2
  • But an amide is written like this:  R(CO)NH2 or CH3-C=O-NH3 or CH3CONH2 or RCONH2
  • An amine is more often seen as a “straight-chain” amine
  • An amide has that C=O double bond next to the Nitrogen. It looks like a spaceship (or a phallus)

10 Responses

  1. I like this…its simple and too the point

    • Thanks! I try. 🙂

  2. or CH3-C=O-NH3

    should that not be NH2?

    • Yes, you’re right. BUT if if it has an extra H on the N atom, then just assume that it has a positive charge.

  3. under amide, carboxylic acid should read carbonyl

    • You are correct, Sally, the amide picture does show a carbonyl function group. But remember, the ‘R’ ligand next to it also stands for any other molecule. In this case, I am indirectly implying that the ‘R’ ligand is an -OH, which is usually synonymous with amides. Thank you for your astute observation, however.

  4. you sure are “assuming” a lot and have a hard time admitting you made several errors.

    • They’re not errors. You should know that these assumptions are able to be made by definition of these terms and conventional notations.

      • Yes! You tell him, Misty! 😀

  5. Misty, please clarify because you are mistaken also. The “expert” here specifically states an “amide is a nitrogen with a carboxylic acid” which is completely misleading and fundamentally incorrect. Furthermore, by definition an amine is a derivative of ammonia where one or more hydrogen atoms are REPLACED by an alkyl group, an R-grpoup, or a hydrocarbon chain (call it what you want)…therefore you will never see NH3 in an amine, at best you’ll have NH2 connected to an R-group. And I already pointed out your error in your amide definition. You, sir, should not be teaching anyone Organic Chemistry. And anyone, Misty, that cannot see this should reread their Orgo text. No offense intended.

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