CHAPTER 9: Organic Compounds

Fractional Distillation

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Fossil fuels: form the major part of our fuel

resources and they are derived from the fossil
remains of living organisms, which have been
altered by heat and pressure.
The three main groups of fossil fuels are natural
gas, petroleum and coal, derived from crude oil.

Crude oil is separated in a fractionating tower,

where it undergoes fractional distillation.
Each fraction or component is made up of a
range of hydrocarbons with similar boiling points
and hence molecular masses. Components with
lower boiling points are drawn up closer to the top.

Cracking- heavier hydrocarbons are broken into

smaller molecules, using heat and a catalyst.
One product has a carbon=carbon double bond.

Organic chemistry is the study of the structure, properties, and reactions of compounds of carbon
(excluding carbonates, simple oxides of carbon (such as CO and CO2), allotropes of carbon such as
diamond ,graphite and graphene).

Why do carbon compounds form so many compounds?

 Each carbon atom has _____ valence electrons – so each C atom forms _____ bonds.

 Bonds between carbon atoms can be ______________, _______________ or

_________________ bonds.

 Carbon atoms can form strong _________________ bonds with other carbon atoms or with
atoms of other elements such as H, O, Cl, N, S, F, I.

Because there are so many organic compounds possible, they are classified into families of compounds
or homologous series.
The members of a homologous series have similar chemical properties and each member differs from
the next by a ______ group.

The important homologous series to be aware of in unit 1 include: alkanes, alkenes, alkynes, alkyl
halides, alcohols, carboxylic acids, esters.

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Formulae Used to describe Molecules

1. Molecular formula

The molecular formula describes the actual number of atoms of each element present in a molecule of a
compound.
The molecular formula is always a whole number multiple of the empirical formula.
Example: the molecular formula of ethene is C2H4

2. Structural formula

The structural formula depicts the arrangement of atoms in a molecule in a diagrammatical manner.

The structural formula for ethene is

If asked to ‘show all bonds’ – expand all groups including CH3 and OH.

(show bond angles, preferably, and never use a solid line for electrostatic attractions)

3. Semi -Structural Formula

The semi-structural formula is an abbreviated form of the structural formula. It clearly describes the
arrangement of atoms without using a diagram.

The semi-structural formula of ethene is CH2CH2

Hydrocarbons

 compounds that consist only of ________________ and ________________ atoms.

 derived from petroleum (coal, oil, natural gas).

 form non-polar molecules.

 their intramolecular forces are strong ________________ bonds.

 their intermolecular forces are _____________________ forces. Small hydrocarbons are

__________ at room temperature.

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Naming Hydrocarbons

To write the systematic name of a hydrocarbon molecule, we apply the following set of rules:

Step 1: Identify the longest continuous unbranched chain (backbone) of carbon atoms.

Step 2: a. Count the number of carbon atoms in the main chain and assign the corresponding prefix.

C Number Prefix C Number Prefix

1 Meth
2 Eth
3 Prop
4 But
5 Pent
6 Hex
7 hept
8 oct
9 non
10 dec

Add the prefix ‘cyclo’ if the molecule displays a cyclic structure.

b. Determine if the molecule is an alkane, alkene or alkyne and add the suffix, ‘ane’, ‘ene’ ‘yne’
respectively.

Step 3: Number the chain so that the multiple bond receives the lowest assigned number.

In the event of the numbering being the same in two different directions, ‘the first point of difference rule’
is applied.

The ‘first point of difference rule’ states that the first time a difference in numbering occurs, numbering
should be done in such a way as to give the lowest number at this first difference.

Step 4: Indicate the position of any multiple bonds by inserting the corresponding carbon number at the
front or into the middle of the hydrocarbon name.

Eg. 1-butene or but-1-ene

Step 5: State the position and type of alkyl group/s (branch) at the beginning of the hydrocarbon name.
Separate the numbers from the letters with hyphens.
Name the branch with the ending-yl. Alkyl groups have the symbol R. They have 1 less hydrogen than
their parent alkane.
If two identical side chains are present , use ‘di-‘ as a prefix, for three use ‘tri-‘

Eg. 1,1,1-trichloro-2,2-dimethylpropane.

Where different alkyl groups are attached to the same chain, the y are written in alphabetical order.

Eg. 3-ethyl-2-methylhexane

When two or more branches occur on the same carbon, the number of that carbon must be indicated for
each branch.

Eg. 2-ethyl-2-methylpentane

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The name is written as a single word using hyphens to separate the different prefixes and commas to
separate numbers.

Alkanes

 the simplest homologous series of hydrocarbons

 of general formula ______________

 they have only ______________ carbon-carbon bonds

 are ________________ hydrocarbons because

__________________________________________________________

 are named so that their prefix indicates the number of carbon atoms in each molecule.

 the name of each alkane ends in ane (alkane)

Isomers
 molecules with the same molecular formula but different structural formula are called

_________________________________________ .

 they have different __________________ and _________________ properties and so are

named differently.

 as the number of carbon atoms increases, the number of _______________ increases.

Example 1
Draw the structural formulas for the first 3 alkanes:

a) b) c)

Example 2
Write the semi-structural formulas for the first 3 alkanes.

a) b) c)
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Example 3
Draw the 2 possible structures for the alkane with 4 carbon atoms.

Example 4

Draw the structural formula and name the compound described by the semistructural formula
CH3CH2CH(CH3)CH3.

Example 5
Draw the structural formulas, name and give the semi-structural formulas for the isomers of hexane.

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Functional Groups

 a functional group is a bond, an atom or a group of atoms that gives a characteristic set of
chemical properties to a molecule containing that bond or group.

Alkanols

 the systematic name for the group of chemicals commonly called _______________.

 contain the _______________ functional group, –OH

 have the general formula _______ (R is an alkyl group).

 soluble in water because they form _______________________ with water molecules.

 have higher boiling points (forming H bonds with their own
molecules) compared to the corresponding alkanes.

Note that as the length of the hydrocarbon stem increases

in alkanols, the influence of the –OH group becomes less
significant. The properties of the longer chained alkanols
tend more towards those of the corresponding alkanes.

 due to the –OH group, alkanols are more reactive than their
corresponding alkanes.
 Alkanols are named by replacing the –ane of the
corresponding alkane with ‘-ol’.
Where the –OH functional group can be placed on different carbon atoms in the stem, again,
numbers are used to indicate the position of the functional group.
e.g. isomers of butanol
H OH
H H OH H HO C H H C H
H H C C H C C H
HO C C H H C C H H H
H C H H C H
C C C C
H H H H H H H H H H
H H H H H H

butan-1-ol butan-2-ol methylpropan-1-ol methylpropan-2-ol

There are 3 types of alkanols

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 H H H H
C H H H C H
C
H C O H C C H
H C H O HC
H
H
H H H H
10 (primary) 20 (secondary) 30 (tertiary)

The -OH group is attached The -OH group is attached The -OH group is attached
to a C atom which is to a C atom which is to a C atom which is
attached to _____ other attached to _____ other attached to _____ other
C atom. C atoms. C atoms.

Alkenes

 contain carbon-carbon _________________bond

 of general formula _____________

 unsaturated hydrocarbons because there are __________ than the maximum number of
_______________ atoms

 the name ends in ________

 semistructural formulas often show C = C

Example 6
Draw the structural formulas and provide the semistructural formulas for

a) ethene b) propene

Example 7
There are 3 isomers of butene. Draw them and provide their semistructural formulas.

a) b) c)

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  When naming the isomers of butene, the numbering starts from the end nearest the double bond.

The position of the double bond is indicated by the number of the ______________ carbon atom
involved in the double bond.

 The rules for naming any side chains are similar to those for the alkanes.

Example 8
Draw the structural formulas and provide the semistructural formulas for

a) 2-methylpent-2-ene

b) 3-methylpent-2-ene

c) 3,4-dimethylhex-1-ene

Example 9
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Name each of the following and provide their semistructural formulae. When numbering carbon atoms,
the double bond has priority over a branch.

a) b) c)
H H
H H H
H H H
H C H C
H H H
H C H H C C H C H C H
C
H C C H C H C
H C H C
H
H C C H C
C C H H H C
H H C H C H H C H
C H H C H C
H H H H H H H
H H H H H H

Example 10
Draw the structural formulas and provide the names for

a) CH3CH=CHCH(CH3)CH3

b) CH2=CHC(CH3)2CH2CH3

c) CH2=CHCH2CH(CH2CH3)CH(CH3)CH3

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Alkynes

 contain carbon-carbon _________________bond

 of general formula _____________

 unsaturated hydrocarbons because there are __________ than the maximum number of
_______________ atoms

 the name ends in ________

Haloalkanes

 if a hydrogen atom in an alkane is substituted with an atom of a ______________ (chlorine,

fluorine, bromine or iodine), haloalkanes are formed,

Prefix Halogen
fluoro -F
chloro - Cl
bromo - Br
iodo -I

e.g. there are 2 isomers of chloropropane

H Cl
Cl C H H
H C
C C H C C H
H H H H
H H H H
1-chloropropane 2-chloropropane

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  where functional groups can be located in different positions in a molecule, again, numbering is
used to show where the functional group is attached to the carbon chain.

 if there are any alkyl branches in a molecule, their names and positions are also included in the
name.

 where a molecule has both a functional group and a branch, the numbering starts from the end
closest to the functional group. This is because the functional has a greater effect on the
chemical and physical properties of the molecule.

e.g. 2-chloro-3-methylbutane
The numbering starts from the end closest to the
chloro functional group, not from the end closest to the
methyl branch.

 more than one hydrogen atom in an alkane can be replaced with a halogen atom

Example 11
Draw the structural and write the semistructural formulas for 2,3-dibromo 3-methylpentane

Reaction of Alkenes

The unsaturated nature of alkenes makes them more reactive than alkanes.
The greater reactivity allows them to participate in addition reactions. In such reactions, the double
bond between the two carbon atoms of the alkene ‘opens up’ and the reactant can attach to these
carbons, leaving only a single bond between the carbon atoms.

There are a few important addition reactions of ethene:

Ethene + Br2 → 1,2 - dibromethane

Ethene + H2O → ethanol
Ethene + HCl → chloroethane
Multiple Ethene molecules → polyethene

These are summarised in a diagram on page 203 of Heinemann Chemistry 1.

Carboxylic Acids
 made from 10 alkanols

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  contain the ______________ functional group

 general formula is R-COOH

 occur widely in nature

No of Common IUPAC name Chemical Common location or use

C name formula
atoms
1 Formic acid Insect stings

2 Acetic acid vinegar

3 Proprionic acid Preservative for stored

grains
4 Butyric acid Rancid butter

 many have strong odours

 weak acids - the highly electronegative O atom of the C = O group attracts the electrons towards
it and away from the –OH group  the –OH group of the –COOH is more polarised than the –OH
group of alkanols  the H atom is more weakly bonded to its O atom and so more easily donated

Example 12
Draw the structural formula of butanoic acid, labelling the + and - atoms.

 form strong hydrogen bond with water molecules  soluble in water (low molecular mass)
 The COOH group can participate in H-bonding (more so than alcohols) through both the C=O
and O-H groups.
 H-bonding between two carboxylic molecules result in forming a dimer
 The longer the chain carboxylic acids have stronger dispersion forces, and so boiling
temperatures increase with molecular weight.
 The larger carboxylic acids become less soluble in water as the length of the non-polar
hydrocarbon chain increases.

 in the name, the stem is determined from the number of C atoms in the longest chain that
contains the -COOH group; oic acid is added at the end of the name – the C atom in –COOH is
counted as C-1

Example 13
Draw the structural formula and write the semistructural formula for 3-methylbutanoic acid

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Esters
 formed by a reaction between ____________ and _____________________________

H2SO4
carboxylic acid + alkanol
  ester + water

 H2SO4 is used as a catalyst or dehydrating agent

 the reaction is called _________________________ or ________________________

Properties of esters

 esters are polar molecules and display dipole-dipole interactions as well as dispersion forces,
(they do not form H-bonds with each other )
 Esters can form weak H-bonds with water
Note: H-bonds can only form between an H attached to FON on one molecule (this is H bond
donor) and a partially negative FON on another molecule, regardless of whether it is bonded to
hydrogen (H bond acceptor)
 Larger molecules will be more soluble in non-polar solvents
 Lower melting and boiling temperatures than for corresponding alcohols.

Naming an ester

 Esters are the products of an alcohol joining with a carboxylic acid.

 The first part of the name is derived from the alcohol(yl) and the second word comes from the
carboxylic acid (oate)

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 Method
 Draw a line between the oxygen and the carbon which is attached to an oxygen via a double
covalent bond.
 The component of the molecule containing the –O represents the section derived from the
alcohol. Count the number of carbon atoms in this component, select appropriate prefix, and add
suffix, yl.
 The component of the molecule containing the =O represents the section derived from the
carboxylic acid. Count the number of carbon atoms in this component, select appropriate prefix
and add the suffix, oate.

Example 14
State the systematic name of:

Example 15
Name the ester formed between
a) methanol and ethanoic acid b) propanol and methanoic acid

Drawing an ester
 the carboxylic acid is drawn first and a ______________ molecule is released

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Example 16
Draw and name the ester formed between
a) methanol and ethanoic acid

b) propanol and methanoic acid

Name Functional Group General Formula Class of Prefix/suffix

compound
Chloro -Cl R-X Alkyl halide Chloro-
Haloalkane
Fluoro -F R-X Alkyl halide Flouro-
Haloalkane
Bromo -Br R-X Alkyl halide Bromo-
Haloalkane
Iodo -I R-X Alkyl halide Iodo-
Haloalkane
Hydroxyl -OH R-OH Alcohol -ol
Hydroxy-
Carboxyl -COOH R-COOH Carboxylic acid -oic acid
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Amino -NH2 R-NH2 Amines -amine
-ylamine
Amino-
Ester -COO R-COO-R1 Esters Alkyl alkanoate

Determining formulas of organic compounds

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