9/11/2014 IB Chemistry higher level organic: introduction

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20.1 - Introduction
20.1.1: Deduce structural formulas for compounds containing up to six carbon
atoms with one of the following functional groups: amine, amide, ester and
nitrile. Condensed structural formulas can use NH
2
, CONH
2
, -COOC- and CN
for these groups.
Amines
Amines make up a homologous series which comprises an alkyl chain
with -NH
2
attached to the chain. This can be in any position of the
chain.
The name of each compound comes from the longest alkyl chain
followed by -ylamine.
An alternative acceptable name takes the amine group as a prefix
amino-. A locant is used in the event of ambiguity.
1-Butylamine or 1-aminobutane
Amines may be primary, secondary or tertiary, depending on the
number of alkyl chains attached to the nitrogen atom.
(primary)
ethylamine
(secondary)
dimethylamine
(tertiary)
trimethylamine
Amides
Simple amides
This homologous series comprises a hydrocarbon chain terminating in
a carbonyl attached to an amine group. The whole group has different
9/11/2014 IB Chemistry higher level organic: introduction
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properties to the two individual parts and is called the amide group, -
CONH
2
.
Amides are considered to be derivatives of carboxylic acids.
Propanamide
N-substituted amides
In N-substituted amides one or both of the hydrogen atoms of the
NH2 group are substituted by another group or atom.
N-methylethanamide
The reason that the two parts function different to the whole is the
interaction between the carbonyl group and the lone pair on the
nitrogen atom. There is delocalisation of the lone pair making the
carbon - nitrogen bond much stronger and more rigid (lack of
rotation). The hybridisation at the nitrogen is effectively sp2 making
the C-N-C bond angle 120.
This has consequences in amino acids and protein structure.
Esters
Esters are considered to be carboxylic acid derivatives, being formed
when a carboxylic acid reacts with an alcohol. They contain the -COO-
linkage joining two alkyl groups.
ethylethanoate
9/11/2014 IB Chemistry higher level organic: introduction
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Esters are fruity smelling neutral compounds that are used as
flavourings and scents.
Nitriles
Nitriles have a carbon attached to a nitrogen atom by a triple bond.
This is also called the cyanide group, CN.
When naming nitriles the carbon of the -CN group is included in the
longest chain.
Ethanonitrile or ethanenitrile
The two spellings of the name are both accepted by IUPAC.
20.1.2: Apply IUPAC rules for naming compounds containing up to six carbon
atoms with one of the following functional groups: amine, amide, ester and
nitrile.
The naming rules for all of the homologous series above follow the
usual scheme.
1. Identify the longest carbon chain - this gives the root of the
name.
2. Identify the functional group and add the prefix or suffix that
names it.
3. In the case of possible ambiguity use a locant (number) to
indicate the carbon in the hydrocarbon chain that holds the
functional group.
Note:
Amines may be attached to any position of the hydrocarbon chain.
Amides are terminating groups, but may have N-substitution.
Esters have two alkyl chains and are named using the chain that
comes from the alcohol first followed by the carboxylate residue
second.
9/11/2014 IB Chemistry higher level organic: introduction
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In all cases carbon atoms making up the functional group are included
in the root.
Examples:
1
The longest carbon chain = 3 carbons = prop-
The amine group = -ylamine
Amine group is on carbon #1
Name = 1-propylamine
2
Longest carbon chain = 2 carbons = eth-
Amide group = -anamide
The amide group is terminating (end of chain) and needs no locant
Name = ethanamide
3
The alkyl group attached to the oxygen has 2 carbon atoms = ethyl
The alkyl group that contains the carbonyl, CO, has four atoms =
butanoate
Name = ethylbutanoate
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4
The longest chain including the C of the CN group = 3 carbons = prop-
The functional group is CN = nitrile
Name = propanenitrile (propanonitrile)
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