Organic

Chemistry
History of Organic Compound
• Initially, it was thought that organic
compounds came only from organisms and,
therefore, were naturally occurring,
• Inorganic compounds came from nonliving
systems.
• However, it was later discovered that
organic compounds can be synthesized
from inorganic compounds.
Organic Compound
• Organic compounds are compounds generally
made up of carbon (C) atoms except
carbides, carbonates, cyanides, and oxides of
carbons (e.g., CO and CO,).
• Organic chemistry now pertains to the
study of any compound generally
comprising C except carbides, carbonates,
cyanides, and oxides of C.
The Carbon Atom
• it is the primary component in millions of
organic compounds.
 Properties of Organic Compounds
Organic compounds play an important role in your life.
Characteristics:
1. combustible
2. lower boiling and melting points than inorganic compounds
3. less soluble In water
4. do not produce salts
5. can exist as two or more different compounds that have the
same molecular formula
6. formed molecularly due to covalent bonds rather than
ionic bonds
7. very high molecular weights
 Inorganic Organic
Compounds Compounds
A. Elements Involved All elements C, H, O, N and S
B. • Physical state Solid Solid, liquid and
Physical gas
Properti • Combustibility Noncombustible Usually,
es combustible
• Melting point Very high Very low
• Boiling point Very high Relatively low
• Solubility in water soluble insoluble
• Solubility in organic insoluble soluble
solvent

• Conductivity in fused/solid conductor nonconductor

HYDROCARB
ONS
 Hydrocarbon
A compound that has
only Hydrogen and
Carbon.
 Hydrocarbon
It can be divided into several
groups based on the type of
bond that exists between the
individual carbon atoms.
Hydrocarbon
Alkanes
Alkenes
Alkynes
 Hydrocarbon
 Alkanes
 All of the carbon –
carbon bonds are
single.
 Hydrocarbon
 Alkenes
 Contains a carbon –
carbon double bonds
 Hydrocarbon
Alkynes
 Contains a carbon –
carbon triple bonds
 HYDROCARBONS

Saturated Unsaturate
HC d HC

Aromatic
Alkanes Alkenes Alkynes
HC
SATURATED
HYDROCARB
ONS
Alkanes
 General formula
Alkanes
 General formula

C1 H 2 (1) + 2
Alkanes
 General formula

C3 H 2 (3) + 2
Alkanes
 General formula

C4 H 2 (4) + 2
 Alkanes
 They are also called saturated
hydrocarbons because they have
the maximum number of hydrogen
atoms per carbon.
 Sources of
Alkanes
The primary source of
alkane is petroleum.
 Petroleum is a complex mixture
of organic compounds.
 Alkanes
 Straight-chain alkanes
 Branched-chain alkanes
 Cyclic alkanes
 Alkanes
Straight-chain alkanes
are named after the
number of carbon atom
they contain.
Alkanes
Number of Name Formula
Carbons CnH2n+2
(n)
1 Methane CH4
2 Ethane C2 H 6
3 Propane C3 H 8
4 Butane C4H10
Alkanes
Number of Name Formula
Carbons CnH2n+2
(n)
5 Pentane C5H12
6 Hexane C6H14
7 Heptane C7H16
8 Octane C8H18
Alkanes
Number of Name Formula
Carbons CnH2n+2
(n)
9 Nonane C9H20
10 Decane C10H22
11 Undecane C H
11 24

12 Dodecane C H
12 26
Alkanes
Number of Name Formula
Carbons CnH2n+2
(n)
13 Tridecane C13H28
20 Eicosane C20H42
30 Triacontane C H
30 62
 Nomenclature
 Unbranched Alkyl Groups
 If we remove one H from an
alkane, we obtain an alkyl
group.
 Names ends in -yl
R’: Alkyl Group
• Example:
Alkane Alkyl Group
CH4 (Methane) CH3 – (Methyl)
CH3CH3 (Ethane) CH3CH2 – (Ethyl)
CH3CH2CH3 CH3CH2CH2 –
(Propane) (Propyl)
Nomenclature of
Compounds
 IUPAC
 International Union of
Pure and Applied
Chemistry
Nomenclature of
Compounds
 A chemical name has typically
four parts in the IUPAC system
of nomenclature.
Nomenclature of
Compounds

PREFIX PARENT LOCANTSUFFIX

How many
What isis
Where and
the
thewhat
primary
primary
are
thesubstituents?
functional
carbons? group?
 Naming Branched- Chain
Alkanes
1. Locate the longest
continuous chain of
carbon atoms; this
chain determines the
parent name for the
alkane.
 Naming Branched- Chain
Alkanes
2. Number the
longest chain
beginning with
the end of the
chain nearer the
substituent.
 Naming Branched- Chain
Alkanes
3. Use the numbers
obtained by rule
2 to designate
the location of
the substituent
group.
 Naming Branched-
Chain Alkanes
4. When two or more substituents are
present, give each substituent a
number corresponding to its location on
the longest chain.
 Naming Branched-
Chain Alkanes
4. * the substituent group should be
listed alphabetically (i.e. ethyl
before methyl)
 Naming Branched-
Chain Alkanes
4. **In deciding alphabetical order,
disregard multiplying prefixes such
as di, tri, etc…
 Naming Branched-
Chain Alkanes
5. When two
substituents are
present on the
same carbon
atom, use that
number twice.
 Naming Branched-
Chain Alkanes

6. When two
substituents are
identical, indicate
this using di, tri,
tetra, and so on.
 Naming Branched-
Chain Alkanes
7. When two chains
of equal length
compete for
section as the
parent chain,
choose the chain
with the greater
number of
substituents.
 Naming Branched-
Chain Alkanes
8. When branching first occurs at an equal
distance from either end of the longest
chain, choose the name that gives the
lower number at the first point of
difference.
2-methylbutane

CH3 CH2 CH CH3

CH3
3-methylpentane

CH3 CH2 CH CH3

CH2 CH3
4-ethylheptane

CH3 CH2 CH CH2 CH2 CH3

CH2 CH2 CH3

3,3-dimethylhexane
CH3

CH3 CH2 C CH2 CH2 CH3

CH3
4-ethyl-3-methylheptane

CH2 CH3

CH3 CH2 CH2 CH CH CH2 CH3

CH3
3-ethyl-2,6-dimethylheptane

CH3 CH3
H3C CH CH CH2 CH2 CH CH3
CH2CH3
2,3-dimethylbutane
CH3

CH3 CH CH CH3

CH3
3-ethyl-5-methyloctane

CH3

CH3 CH2 CH2 CH CH2 CH CH2 CH3

CH2 CH3
2,7,8-trimethyldecane

CH3

CH3 CH2 CH CH CH2 CH2 CH2 CH2 CH CH3

CH3 CH3
3,4,8-trimethyldecane
CH3

CH3 CH2 CH CH CH2 CH2 CH2 CH CH2 CH3

CH3 CH3
2,2,4-Trimethylpentane

CH3 CH3

CH3 CH CH2 C CH3

CH3
3-ethyl-6-methyloctane

CH3 CH2 CH CH2 CH2 CH CH2 CH3

CH3 CH2 CH3

3,3-dimethylpentane
4-ethyl-2-methylnonane
2,3,3-trimethylhexane
Learning Check

A. What is the condensed formula

for
H H H H CH 3CH 2CH 2CH 3

H C C C C H
H H H H
C4H10
B. What is its molecular formula?
Butane
C. What is its name?
Learning Check
A. What is the condensed formula for?
CH3CH2CH2CH2CH2CH3
B. What is the molecular formula? C6H14
C. What is its name? Hexane
1. H H H H H H

H C C C C C C H
H H H H H H
CLASSIFICATION OF CARBON
ATOMS
 Primary – 1o
 Secondary – 2o
 Tertiary – 3o
 Quaternary – 4o
 CLASSIFICATION OF
CARBON ATOMS
 Primary Carbon atom
 a carbon atom that is bonded to
only one carbon atom
 CLASSIFICATION OF
CARBON ATOMS
 Secondary Carbon atom
 a carbon that is bonded to two
other carbon atoms
 CLASSIFICATION OF
CARBON ATOMS
 Tertiary Carbon atom
 a carbon atom bonded to three
other carbon atoms
 CLASSIFICATION OF
CARBON ATOMS
 Quaternary Carbon atom
 a carbon that is bonded to four
other carbon atoms
 CLASSIFICATION OF
CARBON ATOMS
Secondary Carbon

CH3- CH2- CH3-

Primary Carbon Primary Carbon

CLASSIFICATION OF
CARBON ATOMS

CH3
I
CH3- CH - CH3

Tertiary Carbon
 CLASSIFICATION OF
CARBON ATOMS
CH3
I
CH3- C - CH3
I
CH3
Quaternary Carbon
 CLASSIFICATION OF
HYDROGEN ATOMS
 Hydrogens are classified
according to the carbon atom to
which they are attached.
 CLASSIFICATION OF
HYDROGEN ATOMS
1o Hydrogen

CH3
I
CH3- CH - CH2 - CH3

3 Hydrogen
o 2o Hydrogen
 Alkane
Isomerism
 Isomers
 are compounds that have the
same molecular formula but
differ in the way the atoms
are arranged.
Isomers
From the Greek word
isos = “the same”
meros = “parts”
 Isomers have the same parts
put together in different ways.
 Isomers
The existence of isomers
necessitates the use of
structural formulas in organic
chemistry.
 Constitutional
Isomers
 Constitutional Isomers are isomers
that differ in the connectivity of atoms,
that is, in the order in which atom are
attached to each other within
molecules.
Constitutional
Isomers
Butane
versus

Isobutane
 Constitutional
Isomers
BUTANE ISOBUTANE
Continuous-chain alkane Branched-chain alkane
4 straight chain single- 3 carbon atoms with the
bonded carbon atoms 4th carbon attached as a
branch on the middle
carbon of the 3 carbon
chain
Boiling Point: -1oC Boiling Point: -12 oC
Melting Point: -138 oC Melting Point: -159oC
Constitutional
Isomers Pentane

Isopentane

Neopentane
Constitutional
IsomersBOILING DENSITY
POINT
PENTANE 36.1oC 0.626 g/mL
ISOPENTANE 27.8oC 0.620 g/mL
NEOPENTANE 9.5oC 0.614 g/mL
Constitutional
Isomers
MF Possible MF Possible #of
#of Isomers
Isomers C8H18 18
CH4 1 C9H20 35
C2H6 1 C10H22 75
C3H8 1 C15H32 4,347
C4H10 2 C20H42 336,319
C5H12 3 C25H52 36,397,588
C6H14 5 C30H62 4,111,846,76
C7H16 9 3
When to use Prefixes iso, neo, tert &
sec
• "iso" is used when all carbons except one form
a continuous chain.
• "neo" is used when all but two carbons form a
continuous chain.
• "sec" is used when the functional; group is
bonded to a secondary carbon (although this
can be used only for the chain containing four
or more carbons).
• "tert" is used when the functional group is
bonded to a tertiary carbon.
Nomenclature
of Branched-
chain Alkyl
Groups
 Branched-chain Alkyl
Groups
For alkanes with more than two carbon
atoms, more than one derived group is
possible.
Systematic nomenclature for alkyl groups is
similar to that for branched chain alkanes.
Branched-chain Alkyl
Groups
Propyl

Propane

Isopropyl
Branched-chain Alkyl
Groups
Butyl

Butane

sec-butyl
Branched-chain Alkyl
Groups

Isobutyl

Isobutane

tert-butyl
Branched-chain Alkyl
Groups
Isopropyl
• 1-methylethyl group

sec-butyl
• 1-methylpropyl
Branched-chain Alkyl
Groups
Isobutyl
• 2-methylpropyl

tert-butyl
• 1,1-dimethylethyl
Branched-chain Alkyl
Groups

Neopentyl
• 2,2-dimethylpropyl
Branched-chain Alkyl
Groups
The common names,
isopropyl, isobutyl, sec-butyl
and tert-butyl are approved
by the IUPAC for the
unsubstituted group.
Branched-chain Alkyl
Groups
Sec – and tert – prefixes are
italized and hypehenated
therefore should not be
considered in alphabetizing.

tert-
butyl
Branched-chain Alkyl
Groups
• Iso and neo are not
hyphenated and should be
included when alphabetizing

Neopentyl
 Branched-chain Alkyl
Groups
• In deciding the alphabetical order of this
groups, you should disregard structure
defining prefixes that are written in italics
and separated from the name by a
hyphen.
• Tert-butyl precedes ethyl, but ethyl
precedes isopropyl.
 Branched-chain Alkyl
• Groups
Example

4-(1-methylethyl)heptane or
4-isopropylheptane
 Branched-chain Alkyl
• Groups
Example

4-(1,1-dimethylethyl)octane or
4-tert-butyloctane
 Nomenclature
of Complex
Branched-chain
Alkyl Groups
Complex Branched-chain
Alkyl Groups

What about the complex

branched alkyl groups for which
no “simple” or “common” name is
available?
 Complex Branched-chain
Alkyl Groups

IUPAC system of nomenclature

1. Select the longest alkyl chains in
the complex substituent as the
base alkyl group.
Complex Branched-chain
Alkyl Groups
CH3
CH2
CH3
CH3 C CH2

CH2 CH2 CH2 CH2 CH2 CH3

CH3 CH CH2 C CH2 CH2

CH2 CH3
CH3
Complex Branched-chain
Alkyl Groups
CH3
CH2
CH3
CH3 C CH2

CH2 CH2 CH2 CH2 CH2 CH3

CH3 CH CH2 C CH2 CH2

CH2 CH3
CH3
Longest continuous chain – parent chain
Complex Branched-chain
Alkyl Groups
Complex CH3
branched-chain CH2
CH3
alkyl CH3 C CH2

CH2 CH2 CH2 CH2 CH2 CH3

CH3 CH CH2 C CH2 CH2

CH2 CH3
CH3
Simple alkyl group
 Complex Branched-chain
Alkyl Groups
IUPAC system of nomenclature
2. The base alkyl group is then
numbered beginning with the
carbon atom attached to the
main carbon chain.
Complex Branched-chain
Alkyl Groups
CH3
CH2
1 2 3 CH
43
CH3 C CH2

CH2 CH2 CH2 CH2 CH2 CH3

CH3 CH CH2 C CH2 CH2

CH2 CH3
CH3
 Complex Branched-chain
Alkyl Groups

IUPAC system of nomenclature

3. The substituent s on the base alkyl
group are listed with appropriate
numbers, and parentheses are used to
set off the name of the complex alkyl
group.
Complex Branched-chain
Alkyl Groups
CH3
CH2
1 2 3 CH
43
CH3 C CH2

CH2 CH2 CH2 CH2 CH2 CH3

CH3 CH CH2 C CH2 CH2

CH2 CH3
CH3

7-(1,1-Dimethylbutyl)-3-ethyl-7-
methyldodecane
Complex Branched-chain
Alkyl Groups

CH3 CH3

CH3 CH CH2 CH
4 3 2 1

1,3-dimethylbutyl
Complex Branched-chain
Alkyl Groups

CH3 CH2 CH3

CH3 C CH CH2 CH3

1 2 3 4

2-ethyl-1,1-dimethylbutyl
 Nomenclature
of Alkyl Halides
or Haloalkanes
Halogens
Flouro –F
Chloro –Cl
Bromo –Br
Iodo –I
Alkyl Halides
2 WAYS OF NAMING
IUPAC name - Haloalkane
Common name - Alkyl halide
Alkyl Halides
IUPAC name – Haloalkane
1. Apply the rules as in
naming branched-chain
alkanes.
CH 3 CH 2 Br

Bromoethane
Alkyl Halides
IUPAC name – Haloalkane
2. When the parent chain has both a
halo and an alkyl substituent to it,
number the chain from the end
nearer the first substituent,
regardless of whether it is halo or
alkyl.
CH3 CH CH CH2 CH3

Br CH3

2-Bromo-3-
methylpentane
a. 2-bromo-2-methylbutane
b. 2-bromo-3-methylbutane
c. 1-bromo-3-methylbutane
d. 1-bromo-2-methylbutane
 Alkyl Halides
IUPAC name – Haloalkane
3. If two substituents are of equal
distance from the end of the
chain, then number the chain
from the end nearer the
substituent that has
alphabetical precedence.
 CH3

CH3 C Cl

CH3

2-Chloro-2-methylpropane
Alkyl Halides
Common Names: Alkyl
halide
Aka radicofunctional
nomenclature
Also accepted by IUPAC
CH 3 CH 2 Br

“Ethyl bromide”
 CH3

CH3 C Cl

CH3

“tert-Butyl chloride”
 PHYSICAL
PROPERTIES
OF ALKANES
 Physical Properties of
Alkanes
Alkanes are in homologous series.
Homologs – members of a
homologous series
 Physical Properties of
Alkanes
Homologous series
a series of compounds where each
member differs from the next
member by a constant unit. (CH2)
Physical Properties of
Alkanes
At 25oC and 1-atm pressure:
C1 to C4 – gases
C5 to C17 – liquids
C18 and above - solids
 Physical Properties of
Alkanes
Boiling Point
Boiling point of unbranched alkanes
increases with increasing molecular
weights
Branching of alkanes lowers the
boiling point
 Physical Properties of
Alkanes
Melting Point
Cycloalkanes have much higher
melting point that straight-chain
alkanes
 Physical Properties of
Alkanes
Density
Alkanes and cycloalkanes are the
least dense of all groups of organic
compounds.
Density of less than 1g/mL (density
of water at 4o)
Petroleum floats in water
 Physical Properties of
Alkanes
Solubility
Alkanes and cycloalkanes are almost
totally insoluble in water because of their
very low polarity and their inability to
form hydrogen bond.
Soluble in organic solvents such as
benzene, CCl4, chloroform, and other HC.
Cycloalkanes
 Cycloalkanes
Is a saturated hydrocarbon in which
carbon atoms connected to one
another in a cyclic or ring
arrangement are present.
 Nomenclature of
Cycloalkanes
1. Cycloalkanes with 1 ring are
named by attaching the prefix
cyclo- to the names of the alkanes
possessing the same number of
carbon atoms.
 Cyclic molecules
H H H H
CH2 H H
C C CH2
H H
CH2 CH2 C C CH2 CH2
C C HH HH
H H Cyclopropane C C CH2 CH2

H H Cyclopentane
H H

H C C H CH2 CH2
H H
H H CH2
H C C H CH2 CH2 C
CH2 CH2
C C
Cyclobutane H H
H H
H H CH2 CH2
C C
CH2
C
H H Cyclohexane
H H
 Nomenclature of
Cycloalkanes

2. If only one substituent is present, it

is not necessary to designate its
position.
 Br

Bromocyclopropane
 Nomenclature of
Cycloalkanes

3. When 2 substituent are present, we

number the ring beginning with the
substituent first in the alphabet, and
number in the direction that gives the
next substituent the lower number
possible.
 CH3

CH3

1,1-Dimethylcyclohexane
 Nomenclature of
Cycloalkanes

4. When three or more substituents

are present, we begin at the
substituent that leads to the lowest
set of locants.
4-bromo-1,2-dimethylcyclohexane
Note!
1,1-dimethyl-3-propylcyclopentane
1,1-dimethyl-3-butyl-5-propylcyclohexane
 Nomenclature of
Cycloalkanes

5. When the ring system is attached

to a single chain, then it is
appropriate to name the compounds
as cycloalkylalkanes.
cycloalkyl groups

Cyclopropyl Cyclobutyl

Cyclopentyl Cyclohexyl
 CH3 CH2 C CH2 CH3

CH3

3-Cyclobutyl-3-
methylpentane
• Line-angle (Bond-Angle) structural
formula:
– A structural representation in
which a line represents a carbon–
carbon bond.
– A carbon atom is understood to be
present at every point where two
lines meet ( at the intersection).
– At the ends of each lines.
– Example:
Octane

Copyright © Cengage Learning. All rights reserved 152

• Structures of branched-chain alkanes designated
using line-angle structural formulas.
• Example: The five constitutional isomers of C6H14.

Copyright © Cengage Learning. All rights reserved 153

 Answer
a. 1,3-Dimethylcyclohexane
b. 2-Cyclopropylbutane
c. 1-Ethyl-3-methylcyclooctane
d. 1-Bromo-3-methylcyclobutane
e. 1,2,4-Triethylcycloheptane
f. 1-Chloro-2,4-dimethylcyclopentane
 CHEMICAL REACTIONS
OF ALKANES
Alkanes were originally called
“paraffins”.
From the Latin word “parum
affinis” meaning little affinity.
Synthesis of Alkanes and
Cycloalkanes

Hydrogenation of Alkenes
 Synthesis of Alkanes and
Cycloalkanes

Hydrogenation of Alkenes
Alkenes react with hydrogen in the
presence of metal catalyst (Ni, Pt)
to produce alkanes.
 Synthesis of Alkanes and
Cycloalkanes
Hydrogenation of Alkenes
Reaction Mechanism
Addition of H molecule to each
atom of the C = C
 Synthesis of Alkanes and
Cycloalkanes
Hydrogenation of Alkenes
General reaction

Pt or Ni

Solvent
1. CH3 CH = CH CH3 + H-H CH3 CH2 CH2
CH3
2-butene butane

CH3

2. CH3 CH2 CH = CH CH CH3 + H-H

2-methyl-3-hexene
 Synthesis of Alkanes and
Cycloalkanes
Hydrogenation of Alkenes
The reaction is usually carried out by
dissolving the alkene in a solvent such
as ethanol, adding the metal catalyst,
and then exposing the mixture to H2
gas under pressure.
Reactions of
Alkanes
1. Combustion
2. Halogenation
Combustion of
Alkanes
Alkanes are unreactive as
a family because of the
strong C-C and C-H bonds
as well as them being
nonpolar compounds.
Combustion of
Alkanes
At room temperature,
alkanes do not react with
acids, bases, or strong
oxidizing agents.
Combustion of
Alkanes
Alkanes undergo combustion
in air (making them good
fuels):

2 C2H6 + 7 O2  4 CO2 + 6 H2O

Combustion of
Alkanes
Complete combustion
produces:
Carbon dioxide
Water vapor
Combustion of
Alkanes
Incomplete combustion
produces a combination of:
Carbon monoxide
Carbon
Carbon dioxide
Water vapor
Combustion of
Alkanes
Incomplete combustion
produces a combination of:
 CH3-CH2-CH3 + 4 O2 —> CO2 + 2 CO + 4 H2O
+ heat
Combustion of
Alkanes
Carbon dioxide contributes
to global warming.
Carbon monoxide is toxic.
Hemoglobin binds to carbon
monoxide in preference to
oxygen causing suffocation
and even death.
Combustion of
Alkanes
Predict the product of the following
alkanes if it will undergo complete
combustion.
Note: Balance the equation/reaction
1. Methane
2. Pentane
3. Propane
Halogenation of
Alkanes
Halogenation is the
replacement of one or more
hydrogen atoms in an
organic compound by a
halogen.
Halogenation of
Alkanes
In a substitution reaction,
one atom is removed and
replaced or substituted by
another atom or group of
atoms.
Halogenation of
Alkanes
In the presence of light,
alkane undergo substitution
reaction
RH + X2  RX + HX
Example:
RH + Br2  RBr + HBr