Fundamentals of Organic Chemistry

1.1 The carbon atom

Most organic compounds consist of the carbon atom. Able to catenate: ability to form carbon-carbon bonds to produce rings or chains. Atomic number: 6 Electronic configuration: 1s2 2s2 2p2.

1s2 2s2 2p2 Each carbon atom must form 4 bonds covalently.

1.2 Formulae of organic compounds

Organic compound can be represented by: Empirical formula Explanation Simplest formula of a compound which shows the ratio of number of atoms of each element. Shows the actual number of atoms of each element. Shows how each atom is bonded to other atoms Example(ethanoic acid): CH2O

Molecular formula Full structural formula (Displayed formula)

C2H4O2

H H C C H

O O H
H C

Stereo-chemical formula

Shows the 3-dimensional structure of the molecule

HOOC

H H

Note: When drawing full displayed formula, all bonds must be shown including the hydrogens. For example: Full displayed formula of propanoic acid (CH3CH2COOH).

Fundamentals of Organic Chemistry

1.3 Classification of organic compounds
Classification Aliphatic compounds Explanation Open chain of carbon atoms which may be branched or unbranched Carbon atoms arranged in a ring form Example: CH3CH2CH2CH3
H3C HC Br CH3

Alicyclic compounds

Aromatic compounds

Compounds that contain at least one benzene ring

CH3 OH

1.4 Functional groups

A functional group is a group of atoms that determines the chemical properties of the compound. Only the functional group reacts in a chemical reaction. Structure of functional group Contains only C-H and C-C single bonds
H C H C H
C C H

Family name Alkane Alkene

Ending name -ane -ene

Example CH3CH2CH3 Propane

H C H C H H

Ethene Alkyne Arene

H

-yne -

Ethyne
CH3

Methylbenzene Halide Alcohol

R R X OH

-ol

H3C

Br

where X = F,Cl,Br or I where R = any alkyl groups

Bromomethane
H3C CH2 OH

Ethanol

Fundamentals of Organic Chemistry

Amine
R R C R R R C R N R N H R H R R C R N R H

-amine

H3C

NH2

Methylamine

Nitrile Aldehyde

C
O C R H O C R R

-nitrile -al

H3C

C
O C

Ethanenitrile

H3 C

Ethanal Ketone -one

H3 C O C CH3
O H3 C
OH

Propanone Carboxylic acid

R C O

-oic acid
C

Ethanoic acid
Ester
R C O R
O R N H O R C N R R
O R C Cl

-oate
H3C C

O O CH 3

Methyl ethanoate Amide

R C H H O C N R
H

-amide
H3 C C

Ethanamide

Acid Chloride

-oyl chloride
H3 C C

Cl

Ethanoyl chloride Acid Anhydride

O C R O C R O

-oic anhydride

O C H3C O C

O CH3

Ethanoic anhydride

Fundamentals of Organic Chemistry

1.5 Species in organic reactions
Radical
Has odd number of electrons Contain a single, unpaired electron. Extremely reactive. Electron-deficient species. They accept electrons in chemical reactions. Examples: H+, NO2+, Br+ Electron-rich species They donate electrons in chemical reactions. Examples: -OH, CN-, NH3

Electrophile

Nucleophile

1.6 Types of organic reactions

Addition reaction
Occurs when two reactants add together to form a new product with no byproducts.
H C H C H H H H C Br H

Br

C H

Elimination reaction
Occurs when a single reactant splits into two products. Reverse of addition reaction.
H H C Br H C H H H Br H H C H C H

Substitution reaction
Occurs when two reactants exchange parts to give two new products.
H H C H H C H H

uv light
Br Br H

H C H

H C Br H

Hydrolysis
Involves the action of water or its ions to break down a substance into smaller molecules.
O H3 C C O CH3 O

H2O

H3C

C OH

H3C

OH

Fundamentals of Organic Chemistry

Reduction
Involves addition of oxygen atom or removal of hydrogen atom.
H C H C H H H H C H H

2[H]

C H

Oxidation
Involves removal of oxygen atom or addition of hydrogen atom.
O C H3 C H O

[O]

H3C

C OH