Organic chemistry Assistant prof.

Nagham Majed

Organic chemistry

Introduction to Organic chemistry

Organic chemistry :is a is the branch of chemistry that deals with carbon
and its compounds. It is fundamental to biology and medicine. Carbon is
known to form unlimited number of compounds. Carbon atoms can form
chains, they have branches and crosslinks. or rings of all sizes;
Organic chemicals were used in ancient times by Romans and Egyptians
as dyes, medicines and poisons from natural sources, but the chemical
composition of the substances was unknown . In the 16th century organic
compounds were isolated from nature in the pure state and analytical
methods were developed for determination of elemental composition.

Alkane

A hydrocarbon is a compound composed of only carbon and hydrogen.

Figure 1 shows the four classes of hydrocarbons, along with the
characteristic type of bonding between carbon atoms in each class.

Figure 1

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Organic chemistry Assistant prof. Nagham Majed

Alkanes are the simplest type of organic compounds and member of a

larger class of organic compounds called saturated hydrocarbons that
contains only carbon–carbon single bonds. Alkanes have the general
molecular formula CnH2n+2. we can determine the number of
hydrogens in the molecule and its molecular formula. For example,
decane, with ten carbon atoms, must have (2 ×10)+ 2= 22 hydrogen
atoms and a molecular formula of C10H22 .

Nomenclature of Alkanes and the IUPAC System

1. The rules of the IUPAC system for naming alkanes follow

The name for an alkane with an un branched chain of carbon atoms
consists of a prefix showing the number of carbon atoms in the chain
and the ending -ane. The simplest member of Alkane family is methane

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Organic chemistry Assistant prof. Nagham Majed

2. For branched-chain alkanes, select the longest chain of carbon atoms

as the parent chain; its name becomes the root name. If there is one
substituent, number the parent chain from the end that gives the
substituent the lower number.
3. Give each substituent on the parent chain a name and a number. The
number shows the carbon atom of the parent chain to which the
substituent is bonded. Use a hyphen (-) to connect the number to the
name.

A substituent group derived from an alkane by the removal of a

hydrogen atom is called an alkyl group; it is commonly represented by
the symbol R -. We name alkyl groups by dropping the -ane from the
name of the parent alkane and adding the suffix-yl. The substituent
derived from methane, for example, is methyl

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Organic chemistry Assistant prof. Nagham Majed

4. If there are two or more identical substituents, number the parent

chain from the end that gives the lower number to the substituent
encountered first. The number of times the substituent occurs is
indicated by the prefix di-, tri-, tetra-, and so on. A comma is used to
separate position numbers.

5. If there are two or more different substituents, list them in

alphabetical order and number the chain from the end that gives the
lower number to the substituent encountered first

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Organic chemistry Assistant prof. Nagham Majed

Cyclo ALkanes

A hydrocarbon that contains carbon atoms joined to form a ring is

called a cyclic hydrocarbon. When all carbons of the ring are saturated,
the hydrocarbon is called a cycloalkane

Isomers: These are different compounds that have the same molecular
formula. Isomers may be structural isomers or geometrical isomersor
others
Example of structural isomers

Classification of Carbon and Hydrogen Atoms

We classify a carbon atom as primary (1°), secondary (2°), tertiary (3°),
or quaternary(4°)depending on the number of carbon atoms bonded to

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Organic chemistry Assistant prof. Nagham Majed

it. A carbon bonded to one carbon atom is a primary carbon; a carbon

bonded to two carbon atoms is a secondary carbon for example

hydrogen’s are also classified as primary, secondary, or tertiary

depending on the type of carbon to which each is bonded. Those
bonded to a primary carbon are as primary hydrogen’s, those bonded to
a secondary carbon are classified secondary hydrogen’s, and those
bonded to a tertiary carbon are tertiary hydrogen.

Preparation of Alkane

1. Hydrogenation of Alkene

2. Reduction with Alkyl Halide

A) Hydrolysis with Grignard reagent.

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Organic chemistry Assistant prof. Nagham Majed

b) Reduction with Metal and Acid

Reaction of Alkanes

They are quite unreactive toward most reagents, a behavior consistent

with the fact that they are nonpolar compounds containing only strong
sigma bonds.
A) Reaction with Halogens: Halogenation
If we mix methane with chlorine or bromine in the dark at room
temperature, nothing happens. If, however, we heat the mixture to
100°C or higher or expose it to light, a reaction begins at once. The
products of the reaction between methane and chlorine are
chloromethane and hydrogen chloride. What occurs is a substitution
reaction—in this case, the substitution of chlorine for hydrogen in
methane.

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Organic chemistry Assistant prof. Nagham Majed

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Organic chemistry Assistant prof. Nagham Majed

Physical Properties of Alkanes:

The first four n-alkanes are gases, but, as a result of the rise in boiling
point and melting point with increasing chain length, the next 13 (C5-
C17) are liquids, and those- containing 18 carbons or more are solids
physical constants for a number of the n-alkanes., the boiling points and
melting points rise as the number of carbons increases .The processes of
boiling and melting require overcoming the intermolecular forces of a
liquid and a solid; the boiling points and melting points rise because these
intermolecular forces increase as the molecules get larger.
There are somewhat smaller differences among the boiling points of
alkanes that have the same carbon number but different structures. the
boiling points of the isomeric butanes, pentanes, and hexanes are given.
We see that in every case a branched-chain isomer has a lower boiling
point than a straight-chain isomer, and further, that the more numerous
the branches, the lower the boiling point.
The boiling point increases steadily with increasing molecular weight
regardless of the structural composition of the molecule

A- The boiling point decreases by increasing the branching on the

chain, as these branches work to separate the particles from each other,

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thereby reducing Vander Val forces. For example, the boiling points of
the molecular formula C5H12 are:

B- The boiling point increases with the symmetry of the compound

molecule due to the uniformity of its molecule shape, for example:
C6H14 molecular formula

C- The boiling point of cycloalkanes is higher than the boiling point of

alkanes

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Organic chemistry Assistant prof. Nagham Majed

The increase in melting point is not quite so regular, since the

intermolecular forces in a crystal depend not only upon the size of the
molecules but also upon how well they fit into a crystal lattice.
In agreement with the rule of thumb, "like dissolves like," the alkanes
are soluble in non-polar solvents such as benzene, ether, and
chloroform, and are insoluble in water and other highly polar solvents.
Considered themselves as vents, the liquid alkanes dissolve compounds
of low polarity and do not dissolve compounds of high polarity.

The density increases with size of the alkanes, but tends to level off at
about0.8; thus all alkanes are less dense than water. It is not surprising
that nearly all organic compounds are less dense than water since, like
the alkanes, they consist chiefly of carbon and hydrogen. In general, to
be denser than water a compound must contain a heavy atom like
bromine or iodine, or several atoms like chlorine.

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