CHAPTER -1

Introduction and Alkanes

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 Alkanes are Hydrocarbons that contain only
single Bonds general Molecular Formula: CnH2n+2

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 Nomenclature of Alkanes

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 Nomenclature of Alkanes
C4H10 can be arranged in two ways:

C5H12 can be arranged in three ways:

These are constitutional isomers or structural isomers

the same molecular formula but the atoms are linked differently.
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 Nomenclature of Alkanes

C6H14 can be arranged in five ways:

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 Alkyl Substituents

Removing a hydrogen from an alkane results in

an alkyl substituent.

Replace “ane” of alkane with “yl.”

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 Common Names

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 Propyl and Isopropyl

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 Two ways to draw Isopropyl Chloride

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 There are four Butyl Groups

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 n = An Unbranched Chain

Common names sometimes use “n” to indicate an straight-

chain alkane.

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 Primary, Secondary, and Tertiary Carbons

A primary carbon is bonded to one carbon.

A secondary carbon is bonded to two carbons.
A tertiary carbon is bonded to three carbons.

Primary hydrogens are attached to primary carbons.

Secondary hydrogens are attached to secondary carbons.
Tertiary hydrogens are attached to tertiary carbons.
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 “Iso”

Iso is at one end, and the substituent is at the other end.

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 Alkyl Group Names

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 Alkanes Systematic Nomenclature

First identify the longest continuous chain

(this is called the parent hydrocarbon)
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 Add the Name of the Substituent

Number the chain in the direction that gives the substituent

as low a number as possible.

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 Common versus Systematic
Nomenclature

• Common names never have numbers.

• Only systematic names can have numbers.

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 List Substituents in Alphabetical Order

• The correct name is the one that contains the lowest of

the possible numbers.

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 Multiple Substituents

• Chain is numbered in the direction that puts the lowest

number in the name.
• Substituents are listed in alphabetical order (di- and tri- are
not alphabetized).
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 When both have the
same Lowest Number

When both names have the same lowest number, go for the
next lowest number.

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 When both have the same Number

When the same numbers are obtained in both directions, the

first group listed gets the lower number.

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 Cycloalkanes

Skeletal structures do not show Cs and Hs bonded to Cs.

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 Skeletal Structures

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 Mono-Substituted Cycloalkanes

A number is not needed

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 Skeletal Structures

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 Boiling Points

The greater the attractive forces between molecules, the

higher the boiling point.

attractive forces

van der Waals forces

dipole–dipole interactions
hydrogen bonds

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 Boiling Points
• Methane –167.7
°C
• Ethane –88.6 °C
• Propane –42.1 °C
• Butane –0.5 °C
• Pentane 36.1 °C
induced dipole-induced dipole
• Hexane 68.7 °C interactions
• Heptane 98.4 °C van der Waals forces
• Octane
The °Cof the molecule, the higher the boiling
125.7area
greater the surface
point
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 Branching Lowers the Boiling Point

“cigar” “tennis ball”

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 Dipole–Dipole Interactions

Dipole–dipole interactions are

stronger than van der Waals forces.

Van der Waals Van der Waals

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dipole–dipole
 Comparative Boiling Points

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 Comparative Boiling Points

The larger the halogen, the more polarizable it is.

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 Solubility

like dissolves like

Polar compounds dissolve in polar solvents (H2O).

Nonpolar compounds dissolve in nonpolar solvents (hexane).

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 An Oxygen can Drag
Three Carbons into Water

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 Fossil Fuels
• Many alkanes occur in nature, primarily in natural gas and
petroleum.
• Natural gas is composed largely of methane, with lesser
amounts of ethane, propane, and butane.
• Petroleum is a complex mixture of compounds, most of which
are hydrocarbons containing one to forty carbon atoms.

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 Refining of Oil
• Distilling crude petroleum (called refining), separates it into
usable fractions that differ in boiling point.
gasoline: C5H12—C12H26 kerosene: C12H26—C16H34
diesel fuel: C15H32—C18H38
Figure 4.5
Refining crude petroleum. (a) An oil refinery. (b) Schematic of a refinery tower.

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 Petroleum Processing
Fraction Boiling Pt Range ºC Carbon size Typical uses
Gas -164-30 C1-C4 Heating, cooking
Gasoline 30-200 C5-C12 Motor fuel
Kerosene 175-275 C12-C16 Fuel for stoves, diesel
and jet engines
Heating oil Up to 375 C15-C18 Furnace oil
Lubricating 350 and up C16-C20 Lubrication, mineral
oil oil
Greases Semisolid C18-up Lubrication,
petroleum jelly
Paraffin Melts at 52-57 C20-up Candles, toiletries
(wax)
Pitch / tar Residue in boiler High Roofing, asphalt
paving
 10.5 Reactions of Alkanes

• Alkanes, cycloalkanes, and other

hydrocarbons can be:
– Oxidized (by burning) in the presence of excess
molecular oxygen, in a process called
combustion
– Reacted with a halogen (usually chlorine or
bromine) in a halogenation reaction
 Alkane Reactions
The majority of the reaction of alkanes are
combustion reactions
– Complete CH4 + 2O2 CO2 + 2H2O
Complete combustion produces
–Carbon dioxide and water

– Incomplete 2CH4 + 3O2 2CO + 4H2O

• Incomplete combustion produces
–Carbon monoxide and water
– Carbon monoxide is a poison that binds
irreversibly to red blood cells
 Halogenation
Halogenation is a type of substitution reaction, a
reaction that results in a replacement of one group
for another
– Products of this reaction are:
• Alkyl halide or haloalkane
• Hydrogen halide
– This reaction is important in converting unreactive
alkanes into many starting materials for other products
– Halogenation of alkanes ONLY occurs in the presence
of heat and/or light (UV)

H Br
H + Br2 heat or H
light
+HBr