Chem 32 ch. 11

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  1. Carboxylic acid ionizes in water.
    The H detaches from the HOCO and bonds with H2O to make H3O.

    The H can also attach to hydroxide ( HO- ) to make H2O.
  2. How are caboxylic acids names when they lose an H and become ions?
    The "-ic acid" at the end of the name becomes "-ate" or "-ate ion".
  3. What are carboxylate salts?
    Negatively charged carboxylate ions attached to positively charged ions ( like Na+ or K+ ).

    Actually, any ionic compound that doesn't have hydroxide ( OH- ) can be called a salt.
  4. Carboxylate salts ( carboxylate ions bound to positively charged ions ) are much more soluble that carboxylic acids.
    Carboxylate salts ( carboxylate ions bound to positively charged ions ) are much more soluble that carboxylic acids.
  5. Solubility of sodium ( Na ) and potassium ( K ) caroxylate salts...
    Sodium and potassium carboxylate salts are very soluble regardless of how big their carbon chains might be.
  6. Phenols and thiols are acidic.
    They can both lose an H to a base.
  7. What is decarboxylation?
    Decarboxylation is when a carboxylic acid loses the carbon with two oxygens attached ( O=C-O ), leaving the H in place where the O=C-O used to be.

    The carboxylic acid usually has a betaketone.
  8. Carboxylic acids with beta-ketones can be decarboxylated just by heating them.
    Carboxylic acids with beta-ketones can be decarboxylated just by heating them.
  9. Oxidative decarboxylation...

    CO2 is removed

    Remaining H and H from neighboring Thiol are removed.

    Molecule usually has a ketone on the alpha carbon, next to the carboxylic acid which is on the first carbon.
    A molecule is decarboxylated CO2 ( O=C-O ) is removed, leaving just the H where the Carboxylic acid used to be.

    Then NAD+ ( NADH + H+ ) come a long and take the H from the molecule that had the carboxylic acid ( now removed ) and a neighboring Thiol ( HS... ) so that the S from the Thiol and the C from the other molecule bond to form a thioester.

    The molecule will usualy have a ketone on the alpha carbon, next to the carboxylic acid group which is on the first carbon.
  10. What is an amine?
    An amine has one Nitrogen covalently bonded to at least one Carbon ( the carbons themselves can be parts of alkyl groups, ethane, propane, etc. ).

    If the Nitrogen is bonded to one carbon it is a primary amine. If bonded to two carbons it is secondary amine, three is tertiary amine.
  11. How to name amines...
    An amine that is made of a Nitrogen with a propyl alkyl group and an ethyl group would be named eythlpropylamine.

    The attached alkyls are listed in alphabetical order with "amine" added at the end.

    If a cyclokane is attached to the amine it is named as cyclopentyl amine or cyclohexylamine, etc.
  12. What is an amino group?

    All there is to it.
  13. Primary or secondary amines can hydrogen bond.

    The nitrogen in these amines can act as hydrogen bond acceptors.

    The hydrogen in these amines can act as hydrogen donators.
    Tertiary amines cannot since they are not bound to any hydrogen atoms.

    Because of this the bond between tertiary amines is weaker than the bond between secondary or primary amines. It also means that the boiling point of secondary and primary amines are higher than the boiling point of tertiary amines.
  14. Most amines are bases.
    Most amines are bases.
  15. Amino acids...
    Amino acids are acids that have both an amino group and a carboxylic acid group.

    Amino acids are amphiprotic.
  16. Zwitterion ( zvitterion )...
    Zwitterions are the ionic form of an amino acid.

    The carboxylic acid group loses an H and the amino group gains an H.
  17. Ionic salts...
    Amine groups ( NH2, NH3 ) can act as bases of course and can add another H to the N, giving the N a positive charge.

    That positively charged N+ can now ionically bond with a negatively charged ion like Cl- and form a Ionic Salt.
  18. What does phenylethylamine look like?
    N-C-C-benzene ring. And probably some other stuff added to it.
  19. What are alkaloids?
    Alkaloids are amines that are made by plants that have a physiolocial affect on the body.

    Nicotene, morphine, caffeine are all alkaloids.

    Alkaloids are bases, so they can react with acids to form salts. These salts are water soluble, can form hydrogen bonds, and have higher boiling points.
  20. Dominant form of a carobxylate acid at physiological pH ( 7.35 )...
    Carboxylic acids ( molecules with a carboxylic acid group ) in a physiological pH will lose the Hs off their carboxilic acid groups ( 99% of them will anyway ) and result in a negatively charged ion.

    This negatively charged form of the molecule is called its dominant form.
  21. Amines, being basic, gain Hs and are converted to conjugate acids at physiological pH.
    If the amine group is part of or attached to an aromatic ring / benzene then it is a very weak base and is not as likely to attract an H.

    If the amine is attached to an alkyl group it is a much stronger base and will attract an H.
  22. Carboxylic acids are usually deprotonated...
    meaning they lose the H ( proton ).
  23. Amines are usually protonated...
    meaning they gain an H ( proton ).
  24. Phenethylamines look like...
    a benzene ( aromatic ring ) attached to a two C alkyl attached to an amine...

  25. Tryptamines look like...
    a benzene ring attached to a cyclopentene that contains a N with an H attached and also some kind of alkyl group attached.
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Chem 32 ch. 11
2011-11-09 07:30:49
organic acid base amine amide ester esther thiol phenol

Chem 32 ch. 11
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