ch.27 amines, amino acids, and polymers
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amine
R - NH2 derived from ammonia NH3 1 or more H replaced by a carbon chain
naming amines
-amine when at end of chain n - amino when in middle of chain 2* or 3* when the same alkyl group di or tri - (alkyl) amine when multiple different groups attached to N N-(group), N-(group) (longest group) amine
why do amines act as a base
lone pair accepts a proton dative covalent bond positive ammonium ion
reactions of the amine group of amino acids
reacts with acids to form a salt NH2 —> NH3+
reactions of the oic acid of amino acids
reacts with alkalis to form salts and alcohols to form esters
esterification of the amino acid
amino acid + alcohol and sulfuric acid COOH —> COO(alcohol) amine group also becomes protonated NH2 —> NH3+ +H2O
zwitterion
when the amine group accepts the H of the COOH forming a - and + ion
isoelectric point
PH at which a zwitterion is formed unique to each amino acid
zwitterion in solution with greater PH
behaves as an acid loses H+ from NH3+
zwitterion in solution with lower PH
acts as a base gains a proton COO- becomes COOH NH3+ stays same
amide
N attached to C=O from reactions of ammonia and acyl chlorides and amines
optical isomerism
molecule with a chiral centre 2 non-superimposable mirror image structures known as optical isomers or enantiomers 1 pair of isomers for every chiral carbon
chiral centre
a carbon attached to 4 different atoms or groups of atoms
condensation polimerisation
joining of monomers with the loss of a small molecule usually water or Hydrogen chloride
polyesters
requires a monomer with 2 x COOH and a monomer with 2 x OH or if 1 has both groups
how much water is released from the esterification
(2n-1) H2O
polyamides
polymers formed by monomers linked by amide linkages formed from 1 monomer with both COOH (or acyl chloride) and an amine or from 2 monomers each containing 2 of the same group
hydrolysing condensation polymers
can be hydrolysed using hot aqueous alkali like NaOH or by hot aqueous acid like HCl
polyester acid hydrolysis
reforms OH and COOH
polyester base hydrolysis
reforms OH and forms carboxylate salt COO-Na+
polyamide acid hydrolysis
reforms COOH forms NH3+
polyamide base hydrolysis
reforms NH2 and forms carboxylate salt COO-Na+
which groups do the OH and H come from
OH from the COOH and H from the NH2 or OH
How to create a primary amine
Excess ammonia and a haloalkane