Organic Chemistry

Introduction to Organic Chemistry

Organic Compounds make up

Foods and foodstuff

Flavours and fragrances
Medicines
Materials, polymers, plastics
Plant, animal and microbial matter; Fertilizers,
natural products
A vast range of manufactured goods
[pharmaceuticals, foods, dyestuffs, adhesives,
coatings, packaging, lubricants, cosmetics, films
& fibres, clothing, etc. etc.]

Some organic chemicals

Medicines

DNA

Materials

Active Pharmaceutical Ingredients

Essential oils

Fuels

Pigments

An organic compound is one that has carbon as

the principal element
An inorganic element is any compound that is not
.an organic compound
Carbon is unique
It has 6 electrons in its outer shell arranges
1s22s2sp2
.It has room for 4 bonds to 4 other atoms
Organic compounds have specific geometry
.around the carbon to carbon bond
If there are four atoms or groups around a
.carbon atom, it has a tetrahedral geometry

Carbon
Carbon Has Four Bonding Electrons
2

C(6) - 1s , 2s , 2px ,
2

1
2py ,

C(6) - 1s , 2s , 2px ,
Hybridization

0 lowest energy
2pz
state

1
2py ,

1 Excited state
2pz

4 sp3

Unique Strong Covalent Bonds

Strong Single, Double and Triple Bonds

Simplest Organic molecule

Carbon has 4 valence electrons

H
H

H
methane

H
H

Ne
Neon

Stable Octet required

Covalent Bonding Atoms Share Electrons

Classification of organic
compounds
Hydrocarbons

Saturated

Unsaturated Aromatic

Hydrocarbon Derivatives

Hydrocarbons
HydrocarbonS are compounds consisting of
only hydrogen and carbon
Hydrocarbons can be classified into:
Saturated hydrocarbons: Compounds in which
carbon bound to carbon by single bonds
Unsaturated hydrocarbons: Compounds in
which carbon may bound to carbon by double,
or triple bonds
The bonds are always nonpolar

Saturated Hydrocarbons
Saturated hydrocarbons:
Have the maximum number of hydrogen atoms
attached to each carbon atom
Alkanes are hydrocarbons with only C-C single
bond.
Each successive compound differs from the
one before it only by a CH2
. CH3CH2CH
Propane

CH3CH2CH2CH3
Butane
9

Saturated hydrocarbons can be:

Straight Chain:
CH3CH2CH2CH3CH3
Pentane (Straight Chain)
Branched

Closed Ring:

Unsaturated Hydrocarbons

Unsaturated Hydrocarbons:
have fewer hydrogen atoms attached to the carbon
chain than alkanes
Alkenes are unsaturated hydrocarbons with
C-C douple bonds

Alkynes are unsaturated

hydrocarbons with C-C triple double bonds

Naming Hydrocarbons
There are two parts:
The first represents the number of the carbon
atoms:
C (meth), 2C (eth), 3C (prop), 4C (but), 5C
(pent), 6C (hex), 7C (hept), 8C (oct) 9C (non), 10 C
()
The second represents the family (Alkane,
Alkene or alkyne)
1

CH3CH2CH2CH3

butane

CH2=CHCH2CH3
CH CCCH

1-butene
2-butyne

12

 Introduction
Aromatic hydrocarbons are compounds
contaninig benzen ring
They are unsaturated
They contain carbon to carbon double bond

Benzene Ring

Compounds that have the same molecular formula,

but different structures (arrangements of the atoms)
.are called isomers
Naming alkanes
.Identify the longest continuous chain
The locations or other groups of atoms attached to
the longest chain are identified and numbered by
counting from the end of the molecule which
.keeps the numbering system as low as possible
Hydrocarbon groups that are attached to the
longest continuous chain and named using the
.parent name and changing the ane suffix to yl

Molecular formula Structural formula

Molecular formula (A)

describes the numbers of
different kinds of atoms in a
molecule
Structural formula (B):
represents a two-dimensional
model of how the atoms are
bonded to each other
Each dash represents a
.bonding pair of electrons

Functional Groups
Functional groups are:
a characteristic feature of organic molecules
that behave in a predictable way.
composed of an atom or group of atoms.
groups that replace a hydrogen atom in the
corresponding alkane
a way to classify families of organic
compounds.
19

Alkenes and Alkynes

Alkenes contain a
double bond between
adjacent carbon atoms.

Alkynes contain a triple

bond
20

Alcohols and Ethers

An alcohol contains
the hydroxyl (-OH)
functional group.
In an ether, an
oxygen atom is bonded
to two carbon atoms.
COC
21

Aldehydes and Ketones

An aldehyde contains
a carbonyl group (C=O),
which is a carbon atom
with a double bond to an
oxygen atom.
In a ketone, the carbon
of the carbonyl group is
attached to two other
carbon atoms.

22

Carboxylic Acids and Esters

Carboxylic acids contain
the carboxyl group, which
is a carbonyl group
attached to a hydroxyl
group.
O

COH
An ester contains the
carboxyl group between
carbon atoms

Amines and Amides

In amines, the
functional group is a
nitrogen atom.
|
N
In amides, the hydroxyl
group of a carboxylic acid
is replaced by a nitrogen
group.

24

Functional Groups

Copyright 2005 by
Pearson Education, Inc.
Publishing as Benjamin
Cummings

25

Learning Check
Classify each of the following as: alcohol,
ether, aldehyde, ketone, carboxylic acid,
ester, amine or amide.
1) CH3CH2CH2OH
2) CH3OCH2CH3
3) CH3CH2NH2
O

4) CH3COH

5) CH3COCH3

26

Solution
1)CH3CH2CH2OH

alcohol

2) CH3OCH2CH3

ether

3) CH3CH2NH2

amine

O
O

4) CH3COH
5) CH3COCH3
carboxylic acid
ester
27

Functional Groups

Hydrocarbon Derivatives

Introduction
Hydrocarbon derivatives are formed when one or
more hydrogen atoms is replaced by an element or a
.group of elements other than hydrogen
Halogens (F2, Cl2, Br2, I2,) can all add to a
.hydrocarbon to form am alkyl halide
When naming the halogen the ine ending is replaced by o
Fluorine becomes fluoro
Chlorine becomes chloro
Bromine becomes bromo
Iodine becomes iodo

.Common examples of organic halides

Alkenes can also add to each other in an addition

.reaction to form long chains of carbon compounds
this is called polymerization
The atom or group of atoms that are added to the
.hydrocarbon are called functional groups
Functional groups usually have multiple bonds or
lone pairs of electrons that make them very
.reactive

Alcohols
An alcohol has a hydrogen replaced by a hydroxyl (-
.OH) group
The name of the hydrocarbon that was substituted
.determines the name of the alcohol
The alcohol is named using the hydrocarbon name
.and adding the suffix ol
If methane is substituted with an OH group it
becomes methanol
If a pentane group is substituted with an OH
.group it is pentanol
For alcohols with more than two carbon atoms we
need the number the chain so as to keep the
.alcohol group as low as possible

Ethers, Aldehydes, and Ketones

An ether has a general formula ROR

Diethyl ether for example would have the formula

CH3CH2OCH2CH3

An aldehyde has a carbonyl group (carbon double

bonded to an oxygen) attached to a terminal carbon
atom
A ketone has a carbonyl group attached to an
.internal carbon atom

The carbonyl group (A)

is present in both
aldehydes and ketones,
as shown in (B). (C) The
simplest example of
each, with the IUPAC
name above and the
common name below
.each formula

Organic Acids and Esters

Organic acids are those acids that are derived from
living organisms, usually from metabolism, but
.sometimes as a defense mechanism
.Long chain organic acids are known as fatty acids
These are also called carboxylic acids as they contain
the carboxyl functional group (COOH)
One oxygen is double bonded to the carbon and the other is
bonded to the carbon and to the hydrogen both with single
.bonds

Esters are condensation products of carboxylic acids

with the removal of water (also called a dehydration
.synthesis)