CMY 127

Organic Chemistry
The Chemistry of Carbon Compounds

Theme 1
Structure and Bonding
Smith: Organic Chemistry
Extracts from Chapter 1 and Chapter 3
 Big ideas in Organic Chemistry
1. Carbon is tetravalent
 Forms single, double and triple bonds

2. Organic molecules have 3D shape

 The shape with lowest energy is preferred
 This shape affects the physical, chemical and biological
properties of the compound

3. Functional groups are sites for chemical reactions

 The distribution of e-density in a FG determines the type of
reactions it can undergo
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Summary of Most Important Functional Groups
alkanes and cycloalkanes have no functional groups

H C
C C C C
O X

alkene alkyne alcohol / alkyl halide

hydroxy- halo-alkane
O

C C C C
C H N C H O
S

aldehyde -amine / ether

alkanal amino- thiol alkoxy alkane
O O O O

C C H C C C
C C C O C O C N

ketone carboxylic acid ester amide

alkanone alkanoic acid alkyl alkanoate alkyl alkanamide

 Blue text denotes IUPAC naming 3

Organic Chemistry & Lecture Classes

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 THE ELEMENT CARBON AND BONDING
 Carbon has 6 electrons with 4 electrons in its outer valence shell
and thus needs to accept 4 additional electrons to fill the valence shell
and satisfy the octet rule.
 Carbon is tetravalent i.e. it forms 4 bonds in stable neutral molecules.
Carbon can form single bonds, double bonds or even triple bonds.

C C C C C C

single bond double bond triple bond

 The intermediate electronegativity of carbon means that it forms
covalent or polar-covalent bonds (expressed as + and -).

H Li
O
C
C H H
H H H 5
H
 Molecular Geometry: VSEPR Theory
(Revise CMY 117)

Valence Shell Electron Pair Repulsion Theory is used to

predict the geometry of a molecule

 Count how many regions of electrondensity there are

around an atom.
 All sets of valence electrons are considered including:
Bonding pairs involved in single or multiple bonds
Non-bonding pairs which are unshared
 Electron pairs repel each other and tend to be as far apart
as possible from each other
 Non-bonding electron pairs tend to repel other electrons
more than bonding pairs do (i.e. they are “larger”)
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Molecular Geometry: VSEPR Theory

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 H
Orbitals for bonding in methane
 The Structure of Methane: sp3 Hybridization
H C H
H
 The structure of methane with its four identical tetrahedral bonds cannot be adequately
explained using the electronic configuration of carbon

2p 2p
Energy

2s + Energy 2s

1s 1s

 Averaging (Hybridization) of the valence orbitals (2s and 2p) provides four new identical
orbitals which can be used for the bonding in methane.
 Orbital hybridization is a mathematical combination of the 2s and 2p wave functions to
obtain wave functions for the new orbitals (Quantum Mechanical Model)
 The Shape of the new hybrid orbital is an average of the shapes of the original orbitals.
++
+ ++ + ++
++
++ ++
+++++ ++++ - ------ --- ++ ++ ++
++++++ +-+------
--- ++++
+++++
+++++++ +++
+ ++++ + - - - ---- = +++
+++++ ++
+
++++ + - - ---- = ++ + +++ ++ ----
+++++++
+++
++++
++++ ++ ++ - ------
+++ --- +++
+++ ++++++-+------
++++
+++
--- ++ ++ ++
+++++++++
+ reinforced, 8
- cancelled
 When one 2s orbital and three 2p
orbitals are hybridized four new and
identical sp3 orbitals are obtained
 When four orbitals are hybridized, four 2s 2py 2px 2pz

orbitals must result hybridization

 Each new orbital has one part s
character and 3 parts p character
 The four identical orbitals are oriented
in a tetrahedral arrangement 4 sp3 orbitals

 The four sp3 orbitals are then

combined with the 1s orbitals of four H
hydrogens to give the -bonding of C
methane. H H
H
tetrahedral methane
with 4 equal bonds

The 3-D shape of molecules has

very important consequences for
their reactivity
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