Topic 4A

Introduction to
organic
chemistry
H
HO C H
C C H H H H H H CH3
H3C C C N C C C CH
O C C C C C C CH3
H H H H
H O H H H
 What are organic molecules?
• simple molecular substance that contains
carbon
Weak intermolecular force
Strong covalent bond
between molecules
within a molecule
 What about polymers?
• NOT simple molecules
• LOTs of C, H atoms + covalent bonds

Lots of covalent bonds!!!

 Simple molecules vs polymer
• A simple molecule has a fixed number of
atoms in each molecule

• A polymer does not have a fixed number

of atom.
• For example, a piece of poly(ethene) may
contain 10000 carbon atoms. A longer one
may contain 1000000.
 Different types of formulae
• Molecular formula
• Tells us the actual number of each atoms
present in one molecule.
• Ethanol has the molecular formula C2H6O,
with 2 C, 6 H and 1 O in each molecule
 Different types of formulae
• Structural formula
• Shows how the atoms are joined together
• One way to simplify displayed formulae
• e.g. Ethanol has the structural formula
CH3CH2OH and CH3-CH2-OH
 Different types of formulae
• Displayed formula
• Shows every atom and every bond
• e.g. Ethanol has the displayed formula:

H H
H C C O H
H H
 Different types of formulae
• Skeletal formula
• Shows only all the bonds between carbon
atoms
• e.g. Ethanol has the skeletal formula:
 Different types of formulae
• Empirical formulae
• Shows the numbers of each atom in the
simplest whole-number ratio
• e.g. Ethane has the molecular formula
C2H6, empirical formula CH3
 Molecular formula of capsacin
• Active component of chili pepper
• Molecular formula: C18H27O3N
H
HO C H
C C H H H H H H CH3
H3C C C N C C C CH
O C C C C C C CH3
H H H H
H O H H H

• Use appropriate formula to represent

molecules
 Checkpoint
• Use different types of formula to
represent:
a) 2,2-dichloropropane
b) 2-methylbutane
 Functional groups
• A functional group in a molecule is an
atom or group of atoms that is responsible
for its chemical reactions
• Examples: COOH, OH, Cl, Br, etc.
 Homologous series
• A homologous series is a family of
compounds with the same functional
group, which differ in formula by CH2 from
the next member
• Examples: CH3COOH, CH3CH2COOH
• CH3OH, CH3CH2OH
• CH3Cl, CH3CH2Cl
Isomerism
 Structural isomerism
• They have the same molecular formula but
different structural formulae.
• Types of structural isomerism:
a) Chain isomerism
b) Position isomerism
c) Functional isomerism
 Structural isomerism
• Chain isomerism
• Refers to molecules with different carbon
chains
• e.g. Butane and methylpropane
 Structural isomerism
• Position isomerism
• Refers to molecules with the same
functional group attached in different
position on the same carbon chain
• e.g. propan-1-ol and propan-2-ol
 Structural isomerism
• Functional isomerism
• Refers to isomers containing different
functional groups
• e.g. propanal and propanone
 Stereoisomerism
• Compounds with the same structural
formula (and the same molecular formula),
but with the atoms or groups arranged
differently in three dimensions
• Types of setereoisomerism:
a) geometric isomers
b) optical isomers (A2 syllabus)
 Geometric isomerism
• Compounds containing a C=C bond with
different atoms or groups attached at the
double bond carbons
• The presence of C=C leads to restricted
rotation
 Geometric isomerism
• When two H atoms are further apart from
each other – they are across the molecule,
we called it a trans isomer or E-isomer
• When two H atoms are on the same side,
we called it a cis isomer or Z-isomer
 Checkpoint
• There are three ways to attach two CH3
groups and two Cl atoms to C=C. Draw
these structures and use your knowledge
of nomenclature and E-Z isomerism to
name them.
 Checkpoint
• There are three ways to attach two CH3
groups and two Cl atoms to C=C. Draw
these structures and use your knowledge
of nomenclature and cis-trans isomerism
to name them.
Cl Cl Cl CH3 Cl CH3

H3C CH3 H3C Cl Cl CH3

Z-2,3-diclorobut-2-ene E-2,3-diclorobut-2-ene 1,1-dichloro-2-

methylpropene
 Electronegativity
• ability to attract a shared electron pair in a covalent bond

x x
H․ H H․H
Each atom attracts the shared pair equally
Shared pair stays in the middle

․․
δ+ δ–
x
x ․ H ․ Cl
H․ Cl ․ Cl has more protons in the nucleus
It attracts the shared pair more
The electron pair is drawn towards Cl
․․
 Polar covalent bond
• When the shared pair is not shared
equally, it creates a polar covalent bond

Positive pole δ+ δ– Negative pole

x
LESS share H ․Cl MORE share

This symbol tells us how the shared electrons

are skewed towards the more electronegative
atom Cl
 Electronegativity compared
• Heteroatoms O, F, Cl, Br, I and N are
more electronegative than C.

• H is less electronegative than C, but the

difference is minimal.

• Hence, the C –H bond is essentially

treated as non-polar covalent bond
 Types of species
• Nucleophiles – electron rich itself and
loves to attack electron poor species

• Electrophiles – electron poor itself and

loves to be attacked by electron rich
species
 Nucleophiles
• Electron pair donor
• Negatively charged species like CN-, OH-
and Cl-
• Neutral species with lone pair like H2O
and NH3
xx xx Lone pair

H․ x O x
․H
Bonding pair
 Electrophile
• Electron pair acceptor
• Positively charged ions like H+, CH3+ and
NO2+
x +
x x
H․ C ․H
x․
H
This is CH3+ now
It has an
a positive
unpairedcharge
electron
 Nucleophile and electrophile
INucleophile
love to attack+ electrophile I→ new
love product
to be attacked
those without by those who are
electrons electron rich
– – – – + + + +
– – – – + + + +

Nucleophile Electrophile
REACTION
– – – – + + + +
– – – – + + + +

Only nucleophiles can attack, not electrophiles

 Radical (very reactive speices)
• Species with unpaired electron/ single
electron, like CH3•
• The dot tells you it’s a radical species, not
an extra electron
x
unpaired electron
x x
H․ C ․H
x․
H
 Structure and reactivity
• Organic molecule is made up of two parts
1.Unreactive long hydrocarbon chain
2.Reactive functional groups (–OH, C=C)

• Why are hydrocarbon chains not reactive?

• Why are functional groups reactive?
 Hydrocarbons are not reactive
• Essentially no electronegativity difference
between C and H
• Covalent pair equally shared,
• no δ+ or δ- on C and H
• Can not attack by nucleophile as it is not
positively charged
• Can not attack electrophile as it doesn’t
have any lone pair
 Functional groups are reactive
• Heteroatoms are present
• They have very different electronegativity
from the C atom
• The covalent bond formed is a polar one
– – – –
– – – –
δ+ δ–
Nucleophile x
–
–
–
–
–
–
–
– C ․ Br
The carbon is slightly electron deficient δ+, nucleophile
can attack the carbon atom when it is bonded to Br
Example 1: C-H bond

x
C․H
I don’t like you,
you have no
charge or
whatsoever
– – – –
– – – –

Nucleophile
– – – –
– – – –
 Example 2: C-O bond

δ+ δ–
x
– – – –
C ․ Br
– – – –

Nucleophile
–
–
–
–
–
–
–
–
δ+ δ–
x
C ․ O
Mechanism in organic chemistry
• Organic reaction is really about
rearranging electrons
• We use curly arrow to show how the
electron moves.

Original position Final position of

of the electrons the electrons
 Bond breaking
Covalent
bond
xx ․․ xx ․․
x
Br x
Br ․ x
Br x ․
x ․ ․ x ․Br․
xx ․․ xx ․․
Homolytic
fission

Br Br 2Br•
 Bond breaking
Covalent
bond
․․ + ․․ –
H x ․ x ․
․ Br․ H ․Br․
․․ ․․
Heterolytic
fission
+ –
H Br H Br
 Types of organic reaction

Addition

A + B C
CH2=CH2 + Cl2 → CH2ClCH2Cl
 Types of organic reaction

Substitution

A + B C + D
CH4 + Cl2 → CH3Cl + HCl
 Types of organic reaction

Elimination

X Y + Z
CH3CH2OH → CH2CH2 + H2O
 Types of organic reaction

Condensation large small

molecule molecule

A + B Y + Z
CH3OH + CH3COOH → CH3COOCH3 + H2O
 Types of organic reaction

Hydrolysis

Y + H 2O A + B
CH3COOCH3 + H2O → CH3OH + CH3COOH
 Types of organic reaction

Polymerisation

nX [X]n
n CH2CH2 → –[CH2CH2]–n
 Working in the lab

Lab coat Eye protection Disposable

gloves
 Hazard
• Any chemical can potential do harm to us
1. Toxicity
2. Absorption through the skin (e.g. 1-bromobutane)
3. Irritation if inhaled (e.g. hydrogen chloride)
4. Corrosive (e.g. concentrated sulphuric acid)
5. High flammability (e.g. ethoxyethane)
6. Carcinogen – cancer causing agent (e.g. benzene)
7. Too much heat produced in a reaction
8. A volatile product which is hazardous to our body is
formed
 Risk
• Depends on the way we deal with a
hazardous chemical

• For example, concentrated sulphuric acid

is very corrosive. This is the intrinsic
property of this chemical. You can do
nothing about it
 Risk
• If we are using a lot of concentrated acid,
then there will be more risky than handling
a small amount

• We can minimise risk, but not hazards

 Ways to minimise risk
1. Working on a smaller scale (using small
quantities)
2. Taking specific precautions (e.g. wearing
gloves)
3. Using alternative techniques (e.g. use a water
bath instead of Bunsen burner for heating if the
chemical is flammable; or performing the
experiment in a fume cupboard)
4. Carrying out the reaction using an alternative
and less hazardous method (e.g. use of less
hazardous chemical)
 Example 1
• Reaction of alkene and bromine can be done by
mixing liquid alkene and pure liquid bromine.
The reaction is extremely fast and violent. The
temperature rises dangerously quickly.

(a) Identify the hazards

Reaction is too violent; bromine is corrosive;
respiratory irritation caused by inhaling alkene;
 Example 1
• Reaction of alkene and bromine can be done by
mixing liquid alkene and pure liquid bromine.
The reaction is extremely fast and violent. The
temperature rises dangerously quickly.

(b) How to reduce the risk?

Cool it in an ice bath to make it less violent
Use bromine water
Use a suitable solvent to dilute the alkene
Run this reaction inside a fume hood
Always wear gloves, eye protection and lab coat
 Fume hood

The hood is
well vented. All
the gases are Glass door to
essentially prevent you from
removed. inhaling the gas