Chapter 28, 29 and 30 - Amines, Polymerisation, DNA Flashcards
What are amines
They are compounds derived from ammonia
They have unpleasant ‘fishy’ odours
How are amines named
Suffix -amine
Prefix amino-
What are the 4 types of amines
Ammonia
Primary amine
secondary amine
tertiary amine
Quaternary salts - not amines
What is the structure of an aliphatic amine
It has an alkyl group attached to the N
What is the structure of an aromatic amine
It has the nitrogen attached directly to a benzene ring
What is a quaternary salt
It is a nitrogen with a positive charge attached to 4 molecules
What do amines act as
weak Bronsted-Lowry bases
What are Bronsted-Lowry bases
Proton acceptors
Why can amines act how they do
They have a lone pair on the nitrogen that can readily accept protons
What does the ability of an amine to act as a base depend on
How well the lone pair on the nitrogen can accept H+
What is the order of base strength from strongest to weakest
Tertiary
Secondary
Primary
NH3
aromatic amine
In aliphatic amines, what causes the ability of a nitrogen to accept H+ to increase
alkyl groups push electrons towards the nitrogen increasing the availability of the N lone pair
Increasing the ability to accept H+
inductive effect
In aromatic amines, what causes the ability of a nitrogen to accept H+ to decrease
The N lone pair is partially delocalised into the benzene ring, reducing the availability of the N lone pair so reducing its ability to accept H+
Reducing the base strength
What are aromatic amines used as
Used in the manufacture of dyes
How are aromatic amines made
Reduction of aromatic nitro compounds
Sn + HCl
How are primary aliphatic amines made
2 stages
From Haloalkane
What is the first stage of making primary aliphatic amines
Nucleophilic substitution
Add CN- in Aqueous Alcohol
Form nitrile
CH3Br + CN- -> CH3CN + KBr
What is the second stage of making primary aliphatic amines
Reduction
Ni catalyst
From nitrile to primary amine
CH3CN + 2H2 -> CH3CH2NH2
What is the other method to making primary aliphatic amines
Haloalkanes react with excess of concentrated ammonia
nucleophilic substitution
CH3Br + 2NH3 -> CH3NH2 + NH4Br
What is the mechanism for making a primary aliphatic amine the other method
Nucleophilic substitution
Lone pair on NH3 attacks carbon
Breaks bond between carbon and bromine towards bromine
Lone pair on NH3 attacks hydrogen
Bond between hydrogen and nitrogen breaks towards nitrogen
What are the advantages and disadvantages of making a primary aliphatic amine the second method
1 step
Doesn’t add another carbon to product
Reaction can repeat and form multiple products
What can happen in the second method after the intial reaction
The product can act as a nucleophile to another haloalkane
This causes further reactions forming a mixture of primary, secondary, tertiary amines and quaternary salts
This method can’t be used to make amines
In the second method what is the main product with excess NH3
primary amine
In the second method what is the main product with excess haloalkane
quaternary salt
What do amino acids contain
Amine group
Carboxylic acid
What are alpha amino acids
Amino acid with 1 carbon between the NH2 and COOH group
What do amino acids exist as in the solid state
zwitterions
Why do amino acids exist as zwitterions
Ionic
High melting point
Usually solids at room temperature
Soluble in water
What do zwitterions look like
Carboxylic acid is COO-
Amine is NH3+
When dissolved in water, what are amino acids sensitive to
pH
What do amino acids look like at a low pH
Amine is protonated - NH3+
Acid is undissociated - COOH
What do amino acids look like at a high pH
Amine unprotonated - NH2
Acid dissociated - COO-
What are the reactions of amino acids like
It involves either the amine or carboxylic acid group
What reactions does the amine group do
Protonated by acids (low pH)
Acylation with acyl chloride/acid anhydride
Nucleophilic substitution with haloalkanes
What reactions does the carboxylic acid in the amino acid do
Deprotonated by bases (high pH)
Acylation with esterification with alcohols (conc H2SO4 catalyst)
What product is made from reacting 2 amino acids
peptides + water
What is the peptide link
The bond between the 2 amino acids
CO -NH
COOH loses OH
NH2 loses H
What are addition polymers
They are long chain molecules formed from lots of small molecules (monomers) joined together to form 1 big molecule (polymer)