Course: B.Sc.

I
Subject: Chemistry I
Unit: III(A)
Organic Chemistry - Introduction
 Organic chemistry is the study of carbon
compounds.

 Animals, plants, and other forms of life consist of

organic compounds.

Intro
Bonding in Organic Compounds
 Besides carbon, the most common elements in
organic compounds are hydrogen, oxygen,
nitrogen, sulfur, and the halogens.

 organic compounds have covalent bonding.

Hydrocarbons
 Hydrocarbons are the most simple organic
compounds.
 Hydrocarbons contain only carbon (C) and
hydrogen (H).
 For classification purposes, all other organic
compounds are considered derivatives of
hydrocarbons.

 Hydrocarbons can be divided into aromatic and

aliphatic hydrocarbons.

Section 14.2
 Hydrocarbons

Aliphatic Aromatic
 Hydrocarbons

Aliphatic Aromatic

Alkanes Alkenes Alkynes

 Hydrocarbons

Alkanes are
hydrocarbons in which
all of the bonds are
Aliphatic
single bonds.

H H

Alkanes H C C H

H H
 Hydrocarbons

Alkenes are
hydrocarbons that
contain a carbon-
Aliphatic
carbon double bond.

H H

Alkenes C C

H H
 Hydrocarbons

Alkynes are
hydrocarbons that
contain a carbon-
Aliphatic
carbon triple bond.

Alkynes

HC CH
 Hydrocarbons

The most common

aromatic hydrocarbons
are those that contain a
benzene ring.
H Aromatic

H H

H H

H
Aliphatic Hydrocarbons
 Aliphatic hydrocarbons are hydrocarbons having
no benzene rings.
 Aliphatic hydrocarbons can be divided into four
major divisions:

 Alkanes
 Cycloalkanes
 Alkenes
 Alkynes
Classification of Hydrocarbons
Alkanes
 Alkanes are hydrocarbons that contain only single
bonds.
 Alkanes are said to be saturated hydrocarbons
 Because their hydrogen content is at a maximum.

 Alkane general formula  CnH2n + 2

 The names of alkanes all end in “-ane.”

 Methane  butane are gases
 Pentane  C17H36 are liquids
 C18H38 and higher are solids
Physical Properties
 No color & odour
 Lower alkane: gases
 Middle alkane: liquids
 Higher alkane: solid
 Higher boiling point : higher molecular wt.
 Branched chain: decrease surface area
 Long chain : higher surface area.
 Even no. of carbon : higher M.P
 Odd no. of carbon : lower M.P
 Higher density: higher mol. Wt
 Non polar : soluble in organic solvent
 Higher mol. Wt : decrease solubility
The First Eight Members of the Alkane Series
All satisfy the general formula CnH2n + 2
Visualization of an Alkane’s Structure
Structural formula – a graphical
representation of the way atoms
are connected
Condensed structural formula –
save time/space and are
convenient

Ball-and-Stick models – 3D
models that can be built by
students
Models of Three Alkanes
 Names, Structural Formulas, Condensed Structural
Formulas, and Ball-and-Stick Models
Methane – Tetrahedral Geometry
Ball-and-
Stick &
Space-
Filling
Models
Carbon’s
four single
bonds form
angles of
109.5o

2
Alkyl Group
 Alkyl group contains one less hydrogen than the
corresponding alkane.
 General abbreviation “R” (for Radical, an
incomplete species or the “rest” of the molecule)

 In naming this group the “-ane” is dropped and “-

yl” is added.
 CH3 is “methyl” (from methane)
 CH2CH3 is “ethyl” from ethane

Section 14.3
Alkyl Group
This group does not exist independently but occurs bonded to another
atom or molecule.
Types of Alkyl groups

 Classified by the connection site

 a carbon at the end of a chain (primary alkyl group)
 a carbon in the middle of a chain (secondary alkyl
group)
 a carbon with three carbons attached to it (tertiary
alkyl group)
Butane
Continuous-Chain or Straight-Chain Structure
Structural C4H10
Formula

Ball-and-Stick
Model
Isobutane (2-methylpropane)
Branched-chain Structure
Structural C4H10
Formula

Ball-and-
Stick
Model
Organic Compound Nomenclature
 Due to the large number, variety, and complexity of
organic compounds, a consistent method of
nomenclature has been developed.

Section 14.3
IUPAC System of Nomenclature
For Alkanes
 Identify the longest chain -- parent
 number from the end closest to first branch
 Name the groups attached to the chain, using the
carbon number as the locator.
 Alphabetize substituents.
 Use di-, tri-, etc., for multiples of same substituent
 combine number and name of substituent with
parent name, separating with hyphen
An Example to Consider
 The longest continuous chain of C atoms is five
 Therefore this compound is a pentane derivative
with an attached methyl group
 Start numbering from end nearest the substituent
 The methyl group is in the #2 position
 The compound’s name is 2-methylpentane.
Longest Chain
 The number of carbons in the longest chain
determines the base name: ethane, hexane.
 If there are two possible chains with the same
number of carbons, use the chain with the most
substituents.

H3C
CH CH2 CH3
CH3
H3C CH2 C CH CH2 CH2 CH3
CH3
Find the longest continuous
carbon chain
1 2 3
CH3 CH2 CH CH3

CH2 CH3
4 5

3-methylpentane
 You must choose the longest
continuous carbon chain
4 3 2 1
CH3 CH2 CH CH2 CH2 CH3

CH2 CH2 CH3

5 6 7

4-ethylheptane
 Number from the end nearest
the first substituent
CH2 CH3

CH3 CH2 CH2 CH CH CH2 CH3

7 6 5 4 3 2 1
CH3

4-ethyl-3-methylheptane
 Number from the end nearest
the first substituent
CH3

CH3 CH2 CH2 CH CH2 CH CH2 CH3

8 7 6 5 4 3 2 1
CH2 CH3

3-ethyl-5-methyloctane
Use “di-” with two substituents

CH3

CH3 CH CH CH3

CH3

2,3-dimethylbutane
Every substituent must get a number

CH3

CH3 CH2 C CH2 CH2 CH3

1 2 3 4 5 6
CH3

3,3-dimethylhexane
 Number from the end nearest
first substituent

CH3

CH3 CH2 CH CH CH2 CH2 CH2 CH2 CH CH3

10 9 8 7 6 5 4 3 2 1
CH3 CH3

2,7,8-trimethyldecane
 Number from the end which has
the “first difference”

CH3

CH3 CH2 CH CH CH2 CH2 CH2 CH CH2 CH3

1 2 3 4 5 6 7 8 9 10
CH3 CH3

3,4,8-trimethyldecane
A More-Highly-Substituted
Carbon Takes Precedence
CH3 CH3

CH3 CH CH2 C CH3

5 4 3 2 1
CH3

2,2,4-Trimethylpentane
 Which end do we number from?

CH3 CH2 CH CH2 CH2 CH CH2 CH3

8 7 6 5 4 3 2 1
CH3 CH2 CH3

3-ethyl-6-methyloctane
Substituents in Organic
Compounds

Section 14.3
Drawing a Structure from a Name
 Draw the structural formula for
2,2,4trimethylpentane.
 Note that the end name is pentane .
 Draw a continuous chain of five carbon (C) atoms,
with four bonds around each.
Drawing a Structure from a Name

 Number the C atoms from right to left.

 Attach two methyl groups (CH3--) to carbon
number 2 and one to number 4.
Drawing a Structure from a Name

 Add necessary H atoms.

 2,2,4-trimethylpentane

Section 14.3
Cycloalkanes
 Members of the cycloalkane group possess rings of
carbon atoms.
 They have the general formula CnH2n.
 Each carbon atom is bonded to a total of four
carbon or hydrogen atoms.
 The smallest possible ring consists of
cyclopropane, C3H6.

Section 14.3
The First Four Cycloalkanes

Note that in the condensed structural formulas, there is a

carbon atom at each corner and enough hydrogens are
assumed to be attached to give a total of four single bonds.

Section 14.3
Drawing the Structure of a
Cycloalkane
 Draw the geometric figure indicated by the
compound’s name , “pentane.”

Section 14.3
 Drawing the Structure of a
Cycloalkane
 Place each substituent on the ring in the numbered
position  “1 chloro-2-ethyl-”
 1-chloro-2-ethylcyclopentane

Section 14.3
Classes of Carbon and
Hydrogen atoms
 1o Carbon - primary carbon is attached to only
one other C atoms

 2o Carbon - secondary carbon is attached to two

other C atoms

 3o Carbon - tertiary carbon is attached to three

other C atoms
CH3CH2CH2CH(CH3)CH2CH3
1o 2o 2o 3o 1o 2o 1o
Types of Hydrogens

48
Derivatives of Hydrocarbons
 Organic molecule characteristics depend on the
number, arrangement, and type of atoms.
 Functional Group – any atom, group of atoms,
or organization of bonds that determine
specific properties of a molecule
 Generally the functional group is the reactive part of
the molecule.
 Due to the functional group’s presence, certain
predictable properties rise.

Section 14.4
Alkenes
 Members of the alkene group have a double bond
between two carbon atoms.
 One hydrogen atom has been removed from two
adjacent carbon atoms, thereby allowing the two
adjacent carbon atoms to form a double bond.

 General formula is CnH2n

 Begins with ethene (ethylene)

 C2H4

Section 14.3
Some Members of the Alkene
Series

Section 14.3
Physical properties:
 Carbon-carbon double bond changes the physicals properties of
alkenes.
 At R.T. , alkenes exist in all three phases, solid, liquids, and gases.

 1. Physical state:
 Ethene, Propene, and Butene exists as colorless gases.
 Members of the 5 or more carbons such as Pentene, Hexene, and
Heptene are liquid
 Members of the 15 carbons or more are solids.

 2. Density: Alkenes are lighter than water

3.Solubility: insoluble in water.
Alkenes are only soluble in nonpolar solvent like
benzene, ether, chloroform.

4.Boiling point : depends on more molecular mass (chain

length).
more intermolecular mass is added, the higher the boiling
point.

5. Melting point : depends on the packaging of the molecules.

Alkenes have similar melting points to that of alkanes,
Naming Alkenes
 “-ane” suffix for the corresponding alkane is
changed to “-ene” for alkenes.
 A number preceding the name indicates the C
atom on which the double bond starts.
 The carbons are numbered such that the double bond
has the lowest number.
 For example, 1-butene and 2-butene

Section 14.3
Example
Write the IUPAC name for each of the following:

CH3

B. CH3─CH2─C=CH─CH3 3 –methyl 2-pentene
 6 5 4 3 2 1
CH3CH CH CH CH CH3
1 2 3 4 5 6
CH3 CH3

Correct name is : 2,5-dimethyl-3-hexene

Note: Always number so that double bond gets the lowest number
Alkynes
 Members of the alkyne group have a triple bond
between two carbon atoms.
 Two hydrogen atoms have been removed from
each of two adjacent carbon atoms, thereby
allowing the two adjacent carbon atoms to form
a triple bond.

 General formula is CnH2n-2

 Begins with ethyne (acetylene)
 C2H2

Section 14.3
Some Members of the Alkyne
Series

Section 14.3
Physical properties
1. Physical properties:
- First 3 members of alkyne : gaseous form
up to C8 : liquid,
more than 8 carbons: solid.
- Colorless & except ethyne all are odorless.
- Lighter than water
- Insoluble in polar and soluble in non polar organic
solvents.
- Melting point, Boiling point and increase with
molecular mass.
 1 2 3 4 5 6 7

Longest chain containing triple bond 2-heptyne

(triple bond)
Location and number of groups?
4-methyl 5-ethyl 6-chloro

Name: 6-chloro-5-ethyl-4-methyl-2-heptyne
 4-bromo-5-methyl-2-hexyne

6-chloro-3,3-dimethyl-4-octyne
GEOMETRICAL ISOMERISM
 The geometrical isomerism arises when atoms or groups are
arranged differently in space due to restricted rotation of a
bond or bonds in a molecule.
 E.g.,
 1) Two different spatial arrangements of methyl groups about a
double bond in 2-butene give rise to the following geometrical
isomers.
 i.e., cis-2-butene and trans-2-butene
 Above two forms are not inter convertible due to restricted rotation of
double bond.
 In the cis isomer, the two methyl groups are arranged on the same side of a
double bond.
 Whereas in the trans isomer, they are on the opposite side.
 2) There are two geometrical isomers (cis & trans) possible in case of 1,4–
dimethylcyclohexane as shown below:


3
 In the above geometrical isomers, the methyl groups are arranged
differently about the plane of the cyclohexane ring. These isomers
are not inter convertible since it is not possible to rotate the bonds
in the cyclohexane ring.

 The geometrical isomers often show different physical and

chemical properties. The difference in their physical properties is
more significant when there is more difference in their polarity.

 Usually the dipole moment of cis-isomers is greater than that of

trans isomers. Hence the cis isomers usually have more solubility
in polar solvents.

 In general, the trans isomers are more stable than cis isomers.
References
1.Organic Chemistry by Morrison and Boyd
2.https://www.google.com
3. https://sites.google.com