27- Amines, Amino Acids And Polymers Flashcards
Primary amine
1 R group
Secondary amine
2 R groups
Tertiary amine
3 R groups
Ammonia
0 R groups
Characteristics of amines
• Pungent smell
• Physiological effects
o Amphetamine (Treats fatigue)
o Phenylephrine (Decongestant)
o Adrenaline (Stress hormone)
How to name a primary amine
• If –NH₂ group is at the end of a chain, add the suffix –amine to the end of the alkyl chain
• If it contains an amine group on any other C other than C-1 the amine is named using the prefix amino- and a number is added to indicate the position
Name this
Ethylamine
Name this
2-aminobutane
How to name a secondary / tertiary amine
• If they contain the same alkyl group, the prefixes di- or –tri are used to indicate the number of alkyl groups attached to the nitrogen
• two or more different groups are attached to a N, the compound is named as a N-substituted derivative of the larger group.
Name these
Name these
What do amines behave as
Weak bases
Why do they behave as weak bases
o Lone pair on N atom can accept a proton
What are amines
Bases
How to form a salt from an amine
• Acid + Amine -> Ammonium Salt
Write reaction between HCl and propylamine
Write reaction between Sulfuric acid and butylamine
What type of reaction are these
Neutralisation
Name or mechanism that prepares primary aliphatic amines
Nucleophilic substitution
Type of reaction that prepares primary aliphatic amines
2 step
How to prepare primary aliphatic amines - overall
- Salt formation
- Amine formation
Step 1 of primary amine preparation - salt formation
• Ammonia acts as a nucleophile as it has a lone pair of electrons on the N.
• Ammonia reacts with haloalkane to form salt
Step 2 of primary amine preparation - amine formation
• Ammonium salt reacts with sodium hydroxide
Conditions of primary amine formation
- ethanol solvent
- excess ammonia
Why ethanol solvent condition - primary amine formation
Prevents substitution of haloalkane with water (to form alcohols)
Why excess ammonia condition - primary amine formation
Reduces further substitution of the amine to form secondary and tertiary amines
Preparation of secondary aliphatic amines - 2 step
Preparation of tertiary aliphatic amines - 2 step
Why can we prepare secondary / tertiary amines this way
primary / secondary amine still contains a lone pair of electrons on the N atom, so can react further with a haloalkane and form a secondary / tertiary amine
Nucleophile in preparation of amines
Ammonia / amine
Preparation of aromatic amines - 2 steps overall
Salt formation
Amine formation
Preparation of aromatic amines - salt formation - conditions
- Tin and conc. HCl act as a reducing agent
- Heated under reflux
Preparation of aromatic amines - amine formation - conditions
- Excess NaOH (aq) is added to produce the aromatic amine
Type of reaction for Preparation of aromatic amines
• Nitroarenes are reduced to form aromatic amines.
Wrote equation for formation of phenylamine