3.3.11 Amines
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What does aliphatic mean?
A straight chain compound with no rings
What is the process with mechanisms for the synthesis of amines?
See card
What compounds are used to make amides?
Acyl chlorides, carboxylic acids and alcohols
How are polyamides produced from acyl chlorides?
The compound will have two acyl chloride groups on either side The chlorine atom is replaced by NH2 - R - NH2 One of the hydrogens connected to the nitrogen is then removed and reacts with chlorine to form HCl This happens on both sides to form a long polymer chain
Why are carboxylic acids used to make polyamides?
They produce water as a biproduct instead of HCl
What is the shape of ammonia?
H | N - H | H
What is the shape of a primary amine?
H | N - H | R
What is the shape of a secondary amine?
H | N - R' | R
What is the shape of a tertiary amine?
R" | N - R' | R
What is the general formula of primary amines?
RNH2 where the R is an aryl or alkyl group
What intermolecular forces are present between amines?
Hydrogen bonds using their NH2 groups The hydrogen bonds are not as strong as in alcohols This makes them soluble in water
What can the lone pair in an amine be used to form a bond with?
A H+ ion when the amine is acting as a base An electron-deficient carbon atom when the amine is acting as a nucleophile
Why are amines considered as bases?
Amines can accept a proton so they are Bronsted-Lowry bases
What does an arrow on a bond signify?
The inductive effect This is caused by groups releasing electrons towards the electron deficient group This increases the electron density which makes it a better electron pair donor
How are primary aliphatic amines produced?
When halogenoalkanes are reacted with ammonia This is nucleophilic substitution by the halide ion NH2
How can phenylamine be produced?
Benzene is reacted with a mixture of concentrated nitric and sulfuric acids which produces nitrobenzene Nitrobenzene is reduced to phenylamine using tin and hydrochloric acid as the reducing agent C6 H5 NO2 + 6 [H] = C6 H5 NH2 + 2H2O
What is a phenyl group?
Cyclohexane with three double bonds connected to an R group
What is the reaction mechanism for the formation of an amide?
See card
How are primary amines produced via the reduction of nitriles?
Nitriles contain the functional group - CN They can be reduced to primary amines with a nickel / hydrogen catalyst R - CN + 2H2 = R - CH2NH2
How is a nitrile formed from a halogenoalkane?
Halogenoalkanes react with cyanide ions is aqueous ethanol The cyanide ion replaces the halide ion by nucleophilic substitution to form a nitrile RBr + CN- = R - CN + Br-