MUDDLE YOUR WAY

THROUGH ORGANIC
MECHANISMS
A VE RY BR IEF INTR OD UCT IO N

KNOCKHARDY PUBLISHING
 KNOCKHARDY PUBLISHING

MUDDLE YOUR WAY THROUGH MECHANISMS

INTRODUCTION
This Powerpoint show is one of several produced to help students
understand selected topics at AS and A2 level Chemistry. It is based
on the requirements of the AQA and OCR specifications but is
suitable for other examination boards.
Individual students may use the material at home for revision
purposes or it may be used for classroom teaching if an interactive
white board is available.
Accompanying notes on this, and a full range of AS and A2 topics,
are available from the KNOCKHARDY SCIENCE WEBSITE at...
www.knockhardy.org.uk/sci.htm

Navigation is achieved by...

either clicking any grey arrows at the foot of each page
or using the left and right arrow keys on the keyboard
MEET THE ATTACKERS

Press the space bar

MEET THE ATTACKERS

I AM A NUCLEOPHILE
I HAVE A LONE PAIR WHICH I CAN
USE TO FORM A NEW BOND.
I ATTACK ELECTRON DEFICIENT
AREAS (with a + or δ+)
MEET THE ATTACKERS

Press the space bar

MEET THE ATTACKERS

I AM AN ELECTROPHILE
I HAVE A + CHARGE or a δ+
CHARGE. I ATTACK ELECTRON
RICH AREAS SUCH AS C=C DOUBLE
BONDS.
MEET THE ATTACKERS

Press the space bar

MEET THE ATTACKERS

AND I AM A FREE RADICAL

I HAVE AN UNPAIRED ELECTRON
WHICH I WANT TO PAIR UP. I AM
VERY REACTIVE AND DON’T MIND
WHERE I ATTACK… WATCH OUT!
 WHO IS ATTACKED?
THE BONDING IN A MOLECULE
INFLUENCES WHAT WILL ATTACK IT
 WHO IS ATTACKED?
THE BONDING IN A MOLECULE
INFLUENCES WHAT WILL ATTACK IT

A typical covalent bond with one shared pair

SINGLE – nothing to tempt an attacking species
 WHO IS ATTACKED?
THE BONDING IN A MOLECULE
INFLUENCES WHAT WILL ATTACK IT

A typical covalent bond with one shared pair

SINGLE – nothing to tempt an attacking species

Bond has twice as many electrons – species

MULTIPLE
which like electrons will be attracted
 WHO IS ATTACKED?
THE BONDING IN A MOLECULE
INFLUENCES WHAT WILL ATTACK IT

A typical covalent bond with one shared pair

SINGLE – nothing to tempt an attacking species

Bond has twice as many electrons – species

MULTIPLE
which like electrons will be attracted

Similar atoms have an equal attraction for

NON-POLAR
the shared pair of the covalent bond
 WHO IS ATTACKED?
THE BONDING IN A MOLECULE
INFLUENCES WHAT WILL ATTACK IT

A typical covalent bond with one shared pair

SINGLE – nothing to tempt an attacking species

Bond has twice as many electrons – species

MULTIPLE
which like electrons will be attracted

Similar atoms have an equal attraction for

NON-POLAR
the shared pair of the covalent bond

δ+
Atoms have different electronegativities and
δ− the shared pair will be attracted more to one
POLAR
end – species known as nucleophiles will be
attracted to the slightly positive end
 WHO IS ATTACKED?
THE BONDING IN A MOLECULE
INFLUENCES WHAT WILL ATTACK IT

A typical covalent bond with one shared pair

SINGLE – nothing to tempt an attacking species

Bond has twice as many electrons – species

MULTIPLE
which like electrons will be attracted

Similar atoms have an equal attraction for

NON-POLAR
the shared pair of the covalent bond

δ+
Atoms have different electronegativities and
δ− the shared pair will be attracted more to one
POLAR
end – species known as nucleophiles will be
attracted to the slightly positive end
 WHAT ATTACKS ALKANES?
ALKANES ARE RELATIVELY UNREACTIVE ORGANIC COMPOUNDS

ALKANES CONTAIN TWO BOND TYPES

C-H and C-C

Both bonds are single – no electron rich areas

Bonds are non-polar - no electron deficient areas

Free radicals are very reactive and do attack

FREE RADICAL SUBSTITUTION

 WHAT ATTACKS ALKENES?
ALKENES ARE MUCH MORE REACTIVE THAN ALKANES

ALKENES CONTAIN A C=C BOND

There will be twice as many electrons between
the carbon atoms as there are in a single bond

C=C bonds is double – an electron rich area

Bonds are non-polar - no electron deficient areas

ELECTROPHILIC ADDITION
 WHAT ATTACKS HALOGENOALKENES?
HALOGENOALKANES ARE MUCH MORE REACTIVE THAN ALKANES

HALOGENOALKANES CONTAIN A POLAR BOND δ+ δ−

The halogen is more electronegative than the
carbon attracts the shared electron pair.

Bonds is single – not an electron rich area

Bonds is polar – the greater electronegativity of

the halogen creates a dipole making the carbon
atom electron deficient.

NUCLEOPHILIC SUBSTITUTION
 MUDDLE YOUR WAY
THROUGH ORGANIC
MECHANISMS

THE END

NOW INVES TI GATE T HE M ECH ANISMS IN

DET AI L

© 2006 J HOPTON & KNOCKHARDY PUBLISHING