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Chapter 12 Introduction to Organic Chemistry: Alkanes

12.1 The Nature of Organic Molecules


What is Organic Chemistry?

The study of organic compounds.

Structure of Organic Compounds


An organic compound
Is a compound made from carbon atoms (one or more Cs and many Hs).
May also contain O, S, N, and halogens.
Carbon is tetravalent
In carbon compounds
Carbon has 4 valence electrons and hydrogen has 1.

C
H

To achieve an octet, C forms four bonds.


CH4 , methane

Count the four bonds:

Organic Molecules may be Polar


What type(s) of intermolecular interactions can be displayed by these molecules?
CH3Cl

CCl4

3D Shapes of Organic Molecules


Remember the VSEPR theory!
A central atom forming four bonds has a tetrahedral shape.
Wedges are used for atoms pointing towards us.
Dashed-lines are used for atoms pointing away from us.

12.2 Families of Organic Molecules: Functional Groups


To study the whole, we look at the parts (i.e. functional groups)
What is a functional group?
A characteristic feature of organic molecules.
An atom or group of atoms within a larger molecule that has a characteristic structure and chemical behavior.
(Memorize table 12.1 on page 365)

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Compounds containing C and H

Hydrocarbons
(Containing only C and H)

Aliphatic

Aromatic

(Open chain and cyclic)

Alkanes

(contain the benzene ring)

Alkenes

Alkynes

Cycloalkanes
and
Cycloalkenes

12.3 The Structure of Organic Molecules: Alkanes and Their Isomers


In Alkanes
We find single bonds only.
A straight-chain alkane has all its carbons connected in a row (we call it backbone).
A branched-chain alkane has branches connected to the backbone.
Constitutional (or Structural) Isomers
They are compounds with the same molecular formula, but different connectivity.
These three compounds have
the formula, C5H12, but their
structures (connectivity) are
different.

H
H

H
H

H
H

H
H

As the number of Cs increases, the number of possible isomers increases exponentially.


(There are 75 isomers for the formula C10H22, and 366,319 isomers for the formula C20H42.)
Why are isomers important?
They have different properties (sometimes dramatically different properties; see table 12.2, page 369.)

12.4 Drawing Organic Structures


Types of Formulas
Molecular formulas show the type and number of atoms of each element in the compound.
Methane
Ethane
Propane
CH4
C2H6
C3H8
Expanded structural formulas (ESFs) show all bonds of all the atoms as lines.

H H

H H H

H C H

H C C H

H C C C H

H H

H H H

Condensed structural formulas (CSFs) are written by giving the name and number of atoms bonded to a particular carbon
right in front of every carbon.

CH4

CH3CH3

CH3CH2CH3

CH3 CH3

CH3 CH2 CH3


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Line-Bond Formulas
The ends and bends are carbons.
We assume every carbon is bonded to as many hydrogen atoms as needed in order to give them four bonds. (Hydrogen atoms
are never shown!)
CH3CH2CH2CH2CH2CH3

12.5 The Shapes of Organic Molecules


Conformers
C-C single bonds are free to spin around and this leads to different 3D geometries (Conformers). Due to this rotation we may
write the same compound in different ways, check this example:
All these structures represent
the same compound (same number
of each type of atom, and same
connectivity.)
In fact, there are an infinite number of possible geometries.

Again, all these structures represent the same compound, make no mistake! They are not isomers!
How can you tell when two or more structures are isomers (different compounds) or conformers (same compound)?
Naming is the key!

12.6 Naming Alkanes


IUPAC System
The names of alkanes
Are determined by the IUPAC (International Union of Pure and Applied Chemistry) system.
In the IUPAC system for organic compounds, a chemical name has three parts: prefix, parent, and suffix.

Prefix
Where are susbtituents
located?

Parent

Suffix

How many
carbons?

What family does the


molecule belong to?

Named by counting the number of C atoms and adding the family suffix -ane.
The first four members have common names.
The family of alkanes forms what we call a homologous series; that is, all the members of the family form a sequence in which
there is a regular difference in the molar mass. The equation that describes the homologous series of the alkanes family is:
CnH2n + 2
(Where n is the number of C atoms.)

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Here is the list of the first twenty members of the alkanes family. Memorize the names for the first ten.
# of C atoms
Formula
Name
1
CH4
Methane
2
CH3CH3
Ethane
3
CH3CH2CH3
Propane
4
CH3CH2CH2CH3
n-Butane
5
CH3CH2CH2CH2CH3
n-Pentane
6
CH3CH2CH2CH2CH2CH3
n-Hexane
7
CH3CH2CH2CH2CH2CH2CH3
n-Heptane
8
CH3CH2CH2CH2CH2CH2CH2CH3
n-Octane
9
CH3CH2CH2CH2CH2CH2CH2CH2CH3
n-Nonane
10
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Decane
11
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Undecane
12
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Dodecane
13
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Tridecane
14
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Tetradecane
15
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Pentadecane
16
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Hexadecane
17
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Heptadecane
18
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Octadecane
19
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Nonadecane
20
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Eicosane
(The n as a prefix to the name stands for normal. It means we are talking about the straight chain alkane no branches.)
Substitution patterns
Carbons can be:
The R represents more Cs.
Primary

Secondary

Tertiary

Quaternary

Alkyl group (Table 12.4, page 381):


It is the part of an alkane that remains when a hydrogen atom is removed. Their names are given by replacing the ane suffix
(from their parent alkane) with yl. Keep in mind that carbon atoms in single bonds rotate freely; therefore, the following
structures and line-bond formulas may take a slightly different shape. You have to be able to identify these side chains
(substituents or branches) in any organic molecule.
methyl

or

CH3

CH3

ethyl

or

CH2

CH3
CH3

CH2

CH2

or

propyl

CH3

or

CH

Isopropyl

CH3

or

CH3 CH2 CH2 CH2

Butyl

CH3

CH

CH2

Isobutyl

or

CH3
CH3

or
CH3

CH2

CH

CH3

sec-butyl
(secondary butyl)

or

tert-butyl or t-butyl
(tertiary butyl)

CH3

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Branched-chain alkanes
Can be named by following four steps:
STEP 1: Name the main chain. Find the longest continuous chain of carbons.
(You have to be careful here, remember free rotation? Make sure you get the longest chain possible.)
The longest continuous chain has five carbons, not four (the straight chain)!

STEP 2: Number the carbon atoms in the main chain. Begin at the end nearer the first branch point:
We want to give the lowest possible numbers to the branches.

STEP 3: Identify the branching substituents, and number each according to its point of attachment to the main chain:
A methyl is attached to C2.

Both, a methyl and an ethyl are attached to C3.

STEP 4: Write the name as a single word.


hyphens separate numbers from letters
commas separate numbers
if two or more different substituent groups are present, cite them in alphabetical order.
for identical substituents use numeral prefixes.
2-methylpentane

3-ethyl-3-methylhexane

3,3-dimethylhexane

Presence of Halogens (Haloalkanes)


When halogens are present as substituents, they receive the following names:
F- (fluoro), Cl- (chloro), Br- (bromo), and I- (iodo)
Cl CH3

CH3CH2CHCHCH3
5
4
3 2 1

3-chloro-2-methylpentane

(Alkyl halides is a common name used for simple molecules.)

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What if?
1. Two different substituents are found at the same distance from both ends?
methyl

ethyl

1
2

What if?
2. In the same molecule theres more than one possible option for the longest chain?
CH 3
CH 3
CH2
CH 3

CH2

CH
CH

CH 2
CH2

CH
CH 2

CH
CH3

CH3
CH
CH 3

CH 3

Remember
In the name there must be as many numbers as substituents in the molecule.
F
F

CH 2

CH 3

CH 3

CH 3

CH 3

CH 2

CH 3

Practice Problem on Naming


Whats the name of the following molecule?

CH 3

CH 3

CH 2

CH 2

CH 3

CH

CH 2

CH 3

CH 2

CH 2

CH 3

12.7 Properties of Alkanes


Properties of Alkanes
Odorless or mild odor.
Colorless.
Tasteless.
Nontoxic.
Have low melting points. (Why?)
Have low boiling points. (Why?)
Flammable.
Soluble in nonpolar solvents.
Insoluble in water.
Not very reactive.

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Properties of Alkanes
At room T (n-alkanes):
First four are gases.
With 5-15 Cs are liquids.
>16Cs are waxy solids.
Properties of Alkanes
The boiling and melting points for the straight-chain alkanes increase with molecular size. WHY?
Boiling Points of Alkanes
Are among the lowest of organic compounds(Why?).

Increase with larger molecules (Why?).

Decrease for branched alkanes (Why?).

12.8 Reactions of Alkanes


Combustion of Alkanes
Alkanes
Undergo combustion by reacting with oxygen to produce carbon dioxide, water, and energy.
alkane + O2

CO2 + H2O + energy

Balancing a Combustion Equation


Write the equation
C5H12 + O2
Balance C
C5H12 + O2
Balance H
C5H12 + O2
Balance O with O2
C5H12 + 8 O2

CO2 + H2O
5 CO2 + H2O
5 CO2 + 6 H2O
5 CO2 + 6 H2O balanced

Halogenation of Alkanes (Substitution)


When alkanes react with halogens,
The reaction is called substitution, one or more H atoms are replaced with a halogen usually Cl or Br.
Light or heat is required.
A mixture of halogenated products result.
CH4 + Cl2

CH3Cl + HCl

chloromethane

Cl2
CH2Cl2 + HCl

dichloromethane

Cl2
CHCl3 + HCl

trichloromethane (chloroform)

Cl2
CHCl4 + HCl

tetrachloromethane, carbon tetrachloride

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12.9 Cycloalkanes
Cycloalkanes
Are cyclic alkanes.
Have 2H fewer than the open chain.
Are named by using the prefix cyclo- before the name of the alkane chain with the same number of carbon atoms.
H2
C

H2
C
H2C

CH2
H2C

CH2

CH2

H2C

H2C

CH2

H2C

Cyclopropane

Cyclobutane
(mp -128 C, bp -33 C) (mp -50oC, bp -12oC)
o

H2C

CH2

H2C

CH2

CH2
C
H2

CH2

Cyclopentane
(all bond angles
are near 109o)

Cyclohexane
(all bond angles
are near 109.5o)

12.10 Drawing and Naming Cycloalkanes


Line-bond (Geometrical) Formulas
Cycloalkanes can be represented by polygons.

Cyclopropane Cyclobutane Cyclopentane

Cyclohexane

Cycloheptane

Cyclooctane

Naming Cycloalkanes
STEP 1: Use the cycloalkane name as the parent. That is, compounds are named as alkyl-substituted cycloalkanes
rather than as cycloalkyl-substituted alkanes. If there is only one substituent on the ring, it is not even necessary to
assign a number because all ring positions are identical.

CH3
methylcyclohexane

STEP 2: Identify and number the substituents. Start numbering at the group that has alphabetical priority, and
proceed around the ring in the direction that gives the second substituent the lower possible number.

CH3

2
3

CH2CH3
1-ethyl-3-methylcyclohexane

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