C27 - Amines, amino acids, polymers Flashcards
What are amines?
Organic compounds derived from ammonia in which one/more H atom has been replaced by a C chain/ring
What two types of amines are there?
Aliphatic amine - N atom attached to straight/branched carbon chain
Aromatic amines - Na atom attached to aromatic ring
What are primary, secondary and tertiary amines?
Primary - N atom attached to one alkyl group
Secondary amine - N atom attached to two alkyl groups
Tertiary amine - N atom attached to 3 alkyl groups
How do you name primary amines?
If NH2 is at end of chain - add suffix ‘amine’ to alkyl chain
If NH2 not on carbon one - prefix ‘amino’ used
How are secondary and tertiary amines named?
If containing same alkyl groups - prefixes di/tri used to indicate number of alkyl groups attached to N atom
If two/more dif groups attached to N atom - N-substituted derivative of larger group
Why do amines act as bases?
Lone pair of electrons on N can accept proton
What is formed when the N on an amine accepts a proton?
Dative covalent bond formed between lone pair of electrons in N and proton
Amine and acids
Ammonium salt
Propylamine + HCl
Propylammonium chloride
Ethylamine + H2SO4
Ethylammonium sulfate
How do you form a primary amine? + conditions
Ammonia + haloalkane —> alkyl ammonium halide salt
Salt + NaOH —> Alkyl amine
Ethanol used as solvent (prevents further substitution by water to produce alcohols)
Excess ammonia used (reduces further substitution of amine group to form secondary/tertiary amines)
How do you form secondary and tertiary amines
Primary amine + haloalkane —> dialkyl ammonium chloride salt
Salt + NaOH —> secondary amine
Repeat with secondary amine to produce tertiary amine
How do you form aromatic amines?
Nitrobenzene heated under reflux with tin and HCl (then excess NaOH) to produce phenylamine and H2O
What is an amino acid?
Organic compound containing amine and Carboxylic acid functional groups
What are alpha amino acids
Amine group attached to second carbon atom, next to carbonyl group
What is the general formula of an alpha amino acid?
RCH(NH2)COOH
Amino acids + HCl
Amino acids + aqueous alkalis (NaOH
Amino acid esterification
Amino acid + alcohol —> ester + water
Acidic conditions
Zwitter ions…
Amino acid with both +ve and -ve charge?
What is an amide
Product of acyl chloride reacting with ammonia/amines
Have amide group C(=O) -NH2
What are primary, secondary and tertiary amides?
Primary - one C atom bonded to N
Secondary - two C atoms bonded to N
Tertiary - three C atoms bonded to N
What is optical isomerism?
Stereoisomers that are non-super impossible mirror images of each other (enantiomers)
When do you see stereoisomerism?
In molecules with a chiral centre - carbon attached to 4 dif atoms/ groups of atoms
How do you signify a chiral centre?
A star/asterisk next to it
How do you draw optical isomers?
3D arrangements
What is condensation polymerisation?
Reaction where two small molecules react to form a larger molecule, eliminating smaller molecule
Two examples of condensation polymers
Polyesters
Polyamides
What bonds link polyesters? What groups are necessary?
Ester linkages
C=O-O-C
Carboxylic acid, alcohol
How can polyesters be made from the same monomer?
Monomers has either alcohol or Carboxylic acid group on either side
How can polyesters be made from two dif monomers
Diol- two hydroxyl groups
Dicarboxylic acid - two carboxyl groups
What is the formula for the water produced in a condensation reaction?
(2n-1)
What bonds link polyamides? What groups are necessary?
Amide link
C=O-NH
Carboxylic acids/ acyl chlorides, amine
How can a polyamide be formed from one type of monomer?
Has carboxylic acid/acyl chloride group on one side, and amine group on other
How can a polyamide be formed from dif monomers?
Dicarboxylic acids (/Acyl chloride)
Diamine
How can polyesters/polyamides be hydrolysed ?
Hot aqueous alkali
Hot aqueous acid
What does base hydrolysis of condensation polymers produce?
Salt and alcohol/amine
What does acid hydrolysis of condensation polymers produce?
Alcohol/amine and carboxylic acid
Acid and base hydrolysis of polyester
Acid and base hydrolysis of polyamides