Organic Molecules:

Saturated
Hydrocarbons
Content Outline

The Carbon Atom: Bonding and Shape

Organic Formulas and Molecular Models
Classifying Organic Compounds
Hydrocarbons
Saturated Hydrocarbons: Alkanes
Carbon Bonding in Alkanes
Isomerism
Naming Organic Compounds
Cycloalkanes
 What is organic chemistry?
Organic Chemistry is the study of compounds containing
carbon.

These compounds occur naturally but can be prepared in a

laboratory.

The early history of organic chemistry included an erroneous

theory.
( i.e. that organic compounds exist only in living organisms).

The German chemist Wöhler disproved this theory in 1828

with the lab synthesis of urea.
 What is organic chemistry?
Carbon can form a vast array of long chain and ring
containing compounds because carbon has the unique
ability to bond to itself.

Organic compounds include drugs, fuels, toiletries,

plastics, and fabrics. You can see why organic chemistry
is such an important field of study.

Lipstick is made of organic molecules.

Cosmetics and perfumes contain organic
compounds.
• Carbon, in combination with hydrogen,
oxygen, nitrogen, and sulfur, forms the basis
for millions of organic compounds.
• Organic molecules form the products used
in:
1. Cosmetics and perfumes
2. Pharmaceutical products
3. Soaps and detergents
4. Paints, varnishes, dyes
5. Many more!
Significance of Carbon Compounds
to Life and Civilization
Significance of Carbon Compounds
to Life and Civilization
Main Atoms in Organic Chemistry
 Lewis Dot Symbols for the Representative Elements
& Noble Gases

Hydrogen has one dot,

representing its 1s electron.
Carbon has four dots (2s2 2p2).

* The dots represent the number of valence electrons for

each atom of a representative element and a noble gas.
 Why bonds are formed…

• Atoms form bonds because the compound

that results is more stable than the separate
atoms.
• Ionic bonds in salts form as a result of
electron transfers.
• Organic compounds have
from sharing electrons (G. N. Lewis,
1916).
 Bonding Possibilities of Main Organic Atoms

Each atom has a limited number of possibilities to

satisfy octet:
1. Nonbonding (electron pair localized on one atom)
2. Bonding (electron pair shared between two
atoms) Valence electrons not used in bonding are called
nonbonding electrons, or lone-pair electrons
Bonding Possibilities of Main Organic Atoms
 Bonding Possibilities of Main Organic Atoms

a. Single bond (1 shared pair)

b. Double bond (2 shared pairs)
c. Triple bond (3 shared pairs)
A Summary of Formal Charges
The Carbon Atom:
Bonding and Shape
The Chemistry of Carbon
The Shapes of Carbon-Containing
Compounds

Valence Shell Electron Pair Repulsion

(VSEPR) theory
– VSEPR theory states that electron pairs
repel each other because they have like
charges.
– The electron pairs will try to spread out as
far as possible around an atom.
Molecular Shapes of Carbon Compounds
Predicted by the VSEPR Bonding Theory
 Molecular Shapes of Carbon Compounds
Predicted by the VSEPR Bonding Theory

Methane

Figure 19.1 Tetrahedral structure of carbon:

(a) a regular tetrahedron;
(b) a carbon atom with tetrahedral bonds;
(c) a carbon atom within a regular tetrahedron;
(d) a methane molecule, CH4
 Molecular Shapes of Carbon Compounds
Predicted by the VSEPR Bonding Theory

Ethene

Figure 19.2 (a) Lewis structure for C2H4. (b) Shape of a molecule
with a carbon-carbon double bond. The hydrogens and carbon form
the vertices of a triangle. The bond angles are 120°.
 Molecular Shapes of Carbon Compounds
Predicted by the VSEPR Bonding Theory

Ethyne
In a triple bond, the carbon has only two
regions for shared electrons. To be
placed as far apart as possible, a linear
arrangement is required.
180°

H:C:::C:H H C C H
 Bonding in Carbon Compounds
• The carbon atom is central to all organic
compounds.
• A carbon atom usually forms four covalent
bonds.
– Single bonds
• Ex: H3C-CH3 in ethane
– Double bonds
• Ex: H2C=CH2 in ethene
– Triple bonds
• Ex: HCCH in ethyne (acetylene)
 Bonding in Carbon Compounds
• An organic compound is classified as
saturated if it contains only single bonds.
– Ex: H3C-CH3 in ethane
• An organic compound is classified as
unsaturated if the molecules possess one or
more multiple carbon-carbon bonds.
– Ex: H2C=CH2 in ethene
– Ex: HCCH in ethyne (acetylene)
Organic Formulas and
Molecular Models
 Formulas and Molecular Models
Structural Formulas or Models are often used in organic chemistry
to illustrate molecules.

For example,

or in the case of a model.

Figure 19.3 Types of formulas and models used to represent
organic molecules. Each diagram is a representation of a
propane molecule.
 Structural Formulas
• In a structural formula, the arrangement of
atoms within the molecule is clearly shown.
• Several shorthand methods have been
developed to write structures.
 Structural Formulas
Bond Line Structures
Do not have C-H or C-C single bonds shown,
they are understood.
Bond Line Structures Condensed Structures

CH3CH2CH2CH2CH3
straight-carbon chain

(CH3)2CHCH2CH2CH3

branched chain of carbon atoms

 Structural Formulas
Three General Rules in Bond Line Structures:
1) Carbon atoms are not usually shown. Instead
a carbon atom is assumed to be at each
intersection of two lines (bonds) and at the
end of each line.
2) Hydrogen atoms bonded to carbon are not
shown.
3) Atoms other than carbon and hydrogen are
shown.
 Structural Formulas
This is an example of how to change a condensed formula
into a bond line structure.

(bond line structure)

The table in the next slide summarizes formulas and

models used in organic chemistry.
 Formula or model Definition
Lewis structure Shows all bonds, all atoms, and all nonbonding e-

Structural formula Same as Lewis structure except nonbonding e-

are not shown

Condensed structural formula Bonds are collapsed so relative positions

of atoms are group together

Bond line structure Only bonds and functional groups are shown and
each endpoint and bend represent carbon atoms

Atoms are shown as balls and bonds as sticks

Ball-and-stick model and the shape is shown at the central atom.

Bonds are omitted and the size of atoms are

Space-filling model emphasized.
 Molecular Models

Models are often used in organic chemistry

to illustrate molecules.
 Molecular Models

Figure 19.3 Molecular models of methane: (a) ball-

and-stick model; (b) space-filling model
 Molecular Models

Figure 19.4 Models of ethane: (a) Lewis structure;

(b) bond-line drawing; (c) ball-and-stick model;
(d) space-filling model
 Classifying
Organic Compounds
 Classes of Compounds
• Classifications are based on functional
group.
• Three broad classes:
– Hydrocarbons: Compounds composed of
only carbon and hydrogen.
– Compounds containing oxygen.
– Compounds containing nitrogen.
 Hydrocarbons
• Alkanes: Single bonds between the
carbons; all carbons are sp3.
• Cycloalkanes: sp3 carbons form a ring.
• Alkenes: Double bonds are present in the
molecule; sp2 carbons.
• Cycloalkenes: Double bond in a ring.
• Alkynes: Triple bonds are present; sp
carbons.
• Aromatic: Contain a benzene ring.
 Compounds Containing Oxygen
• Alcohols: Contain the hydroxyl group as
the main functional group.
• Ethers: Contain two alkyl groups
bonded to an oxygen.
• Aldehydes and ketones: Contain the
carbonyl group, C═O.
• Carboxylic acids: Contain the carboxyl
group, —COOH.
 Compounds Containing Nitrogen

• Amines: Alkylated derivatives of

ammonia.
• Amides: Carboxylic acid derivative with a
nitrogen attached to the carbonyl group.
• Nitriles: Contain the cyano group.
 Functional Groups
• Organic compounds with similar
structures are grouped into classes.

• The members of each class of compounds

contain a characteristic atom or group of
atoms called a functional group.
 Functional Groups
• Functional group - collection of
atoms at a site that have a
characteristic behavior in all
molecules where it occurs

• The group reacts in a typical way,

generally independent of the rest
of the molecule

• For example, the double bonds in

simple and complex alkenes react
with bromine in the same way
Functional Groups with Multiple Carbon–
Carbon Bonds
• Alkenes have a C-C
double bond
• Alkynes have a C-C
triple bond
• Arenes have special
bonds that are
represented as
alternating single and
double C-C bonds in a
six-membered ring
Functional Groups with Carbon Singly Bonded
to an Electronegative Atom
Groups with a Carbon–Oxygen Double Bond
(Carbonyl Groups)
 Summary of Important
Families of Organic Compounds
 Summary of Important
Families of Organic Compounds
 Functional Groups

For example, ethanol (i.e. the alcohol functional group) and

dimethyl ether (i.e. the ether functional group) have the
same molecular formula but the boiling point (b.p.) of
ethanol is 78 C while the b.p. of dimethyl ether is -23 C
because of the structural differences between the molecules.
Survey of Functional Groups
Survey of Functional Groups
Survey of Functional Groups
Survey of Functional Groups
Survey of Functional Groups
Survey of Functional Groups
What combination of functional groups is present
in the following molecules?

morphine norethrindrone,
used in oral contraceptives
Hydrocarbons
 Hydrocarbons

• Hydrocarbons are compounds that are

composed entirely of carbon and
hydrogen atoms bonded to each other
by covalent bonds.
• Fossil fuels – natural gas, petroleum,
and coal – are the principal sources of
hydrocarbons.
 Hydrocarbons

• Hydrocarbons are classified into

two major categories, aliphatic and
aromatic.
– aliphatic (do not contain benzene ring)
• alkanes, alkenes, alkynes, cycloalkanes

– aromatic (contain a benzene ring)

 Hydrocarbons

Figure 19.4 Classes of Hydrocarbons

 Saturated
Hydrocarbons:
Alkanes
 Alkanes
• Compounds with C-C single bonds and C-H bonds
only (no functional groups)
• Connecting carbons can lead to large or small
molecules

60
 Alkanes

• Also known as paraffins or saturated hydrocarbons

• Straight- or branched-chain hydrocarbons with only
single covalent bonds between the carbon atoms.

CH3C
straight-carbon chain

CH3CH2CH2CH2CH3
(CH3)
straight-carbon chain
branched chain of carbon atom
 Homologous Series
• When each member of a series differs from
the next member by a CH2 group, the series
is called a homologous series.
• The members of a homologous series are
similar in structure, but have a regular
difference in formula.
 CnH2n + 2

general formula for open-chain

alkanes
Carbon Bonding
in Alkanes
 Carbon Bonding in Alkanes
Alkanes contain saturated carbon atoms that have four sigma
bonds
Sigma bonds are linear bonds formed by a pair of electrons in
overlapping atomic orbitals.
Carbon has the ability to form two, three, or four sigma bonds
because of its ability to hybridize its valence shell electron
orbitals ( i.e the s and the 2p orbitals) as shown in Figure 19.6.
 Sigma () Bond
• A C-C and C-H single bond result from the
overlap of sp3 orbitals.
• This type of bond is called a sigma ()
bond.
• A sigma bond exists if the electron cloud
formed by the pair of bonding electrons lies
on a straight line drawn between the nuclei
of the bonded atoms.
 Carbon Bonding in Alkanes

Figure 19.6 Schematic hybridization of 2s22px12pz0

orbitals of carbon to form four sp3 electron orbitals.
 Carbon Bonding in Alkanes

Figure 19.7 The tetrahedral nature of sp3 orbitals:

(a) a single sp3-hybridized orbital;
(b) four sp3-hybridized orbitals in a tetrahedral arrangement;
(c) sp3 and s orbitals overlapping to form C-H bonds in
methane.
Isomerism
 Isomerism
• The phenomenon of two or more compounds
having the same molecular formula but different
structural arrangements of their atoms is called
isomerism.
• The various individual compounds are called
isomers.
– e.g. There are two isomers of C4H10.
Figure 19.7 Ball-and-stick models illustrating the structural formulas of
several alkanes.
 Constitutional Isomers
• Isomers that differ in how their atoms are arranged in chains
are called constitutional isomers.
• Compounds other than alkanes can be constitutional
isomers of one another
• They must have the same molecular formula to be isomers
Nomenclature of Unbranched Alkanes
 Alkyl Groups
• Alkyl groups have the general formula CnH2n+1 (one
less hydrogen than the corresponding alkane).
• The name of the group is formed from the name of the
corresponding alkane by simply dropping –ane and
substituting a –yl ending.
CH4 = methane -CH3 = methyl
• The letter R is often used in formulas to mean any of
the many possible alkyl groups.

75
Table 19.3 Table 19.3
Names and
Formulas of
Selected
Alkyl Groups
Primary (1°), Secondary (2°), and Tertiary (3°)
Carbon Atoms

primary

CH3
primary
primary H2
CH C
H3C C CH3
tertiary H2
secondary
Example for Drawing
Isomers
 There are three isomers of pentane, C4H12. Write
structural formulas and condensed structural formulas
for these isomers.
1. Write the carbon skeleton of the compound containing the
longest continuous carbon chain.
C-C-C-C-C
2. Complete the structure by attaching hydrogen atoms
around each carbon.
H H H H H

H C C C C C H CH3CH2CH2CH2CH3

H H H H H
 Isomers of Pentane, C5H12 (continued)
For the next isomer, start by writing a four-carbon chain and
attach the fifth carbon atom to either of the middle carbon
atoms – do not use the end ones. Add 12 hydrogens to
complete the structure.
H
H H
H H C H
CH3

H C C C C H CH3CH2CHCH3 CH3CH2CH(CH3)2

H H H H

•This is the only four-chain compound that can be

written.
 Isomers of Pentane, C5H12 (continued)

For the third isomer, start with a three-carbon chain, attach

the other carbon atoms to the central carbon atom, and
complete the structure by adding 12 hydrogen atoms:
H
H H
H C H CH3 No more isomers of
C5H12 can be written.
H C C C H CH3CCH3
H C H
CH3
H H
H
Alkane molecules are non-polar.

– Carbon-carbon bonds are non-polar,

since they are between like atoms.
– Carbon-hydrogen bonds are only
slightly polar.
– The bonds in an alkane are symmetrically
directed toward the corners of a
tetrahedron.
By virtue of their low polarity, alkane
molecules have relatively low boiling
points compared with other organic
compounds of similar molar mass.
Many organic compounds are derivatives of alkanes. Many of these
compounds have one or more of the following elements in them.

C N O H Cl

S F Br

I
The dashed lines indicate the valence bonds or points of attachment each
element can form. For example nitrogen can form three bonds while
oxygen can only form two bonds.
Naming Organic Compounds
 IUPAC System for
Naming Organic Compounds
• The method recommended by the
International Union of Pure and
Applied Chemistry is systematic,
generally unambiguous, and
internationally accepted.
• Some trivial or common names are still
used.
 Naming Organic Compounds
The name of every organic molecule has 3 parts:
1. The parent name indicates the number of carbons in
the longest continuous chain.
2. The suffix indicates what functional group is present.
3. The prefix tells us the identity, location, and number
of substituents attached to the carbon chain.
 Naming Organic Compounds
• Compounds are given systematic names by a process that
uses

• Follows specific rules

– Find parent hydrocarbon chain
– Carbons in that main chain are numbered in sequence
– Substituents are identified and numbered
– Compound name is written as a single word
– Name a complex substituents as though it were a
compound itself
 IUPAC Rules for Naming Alkanes
1. Select the longest continuous chain of carbon
atoms as the parent compound, and consider all
alkyl groups attached to it as branch chains that
have replaced hydrogen atoms of the parent
hydrocarbon. The name of the alkane consists of
the name of the parent compound prefixed by the
names of the branch-chain alkyl groups attached
to it. CH3
H2
CH C CH3
H3C C C
H2 H2
The longest continuous chain is 6 carbons; the
parent hydrocarbon is hexane.
 IUPAC Rules for Naming Alkanes
2. Number the carbon atoms in the parent carbon
chain from one end to the other, starting at the end
closest to the first carbon atom that has a branch
chain.
3. Name each branch-chain alkyl group and
designate its position on the parent carbon by a
number. 2-methyl

CH3
H2
1 CH 3 C 5 CH3
H3C 2 C 4 C 6
H2 H2

2-methylhexane
 IUPAC Rules for Naming Alkanes
4. When the same alkyl-group branch chain occurs
more than once, indicate this by a prefix (di-, tri-,
tetra-, etc.) written in front of the alkyl group name
(e.g. dimethyl indicates two methyl groups).
The numbers indicating the positions of these alkyl
groups are separated by a comma, followed by a
hyphen, and placed in front of the name.
CH3
H2
1 C 3 C 5 CH3
H3C 2 CH 4 C 6
H2
CH3
CH3

2,2,3-trimethylhexane
 IUPAC Rules for Naming Alkanes
5. When several different alkyl groups are attached to the
parent compound, list them in alphabetical order (e.g.
ethyl before methyl as in 3-ethyl-4-methyloctane).
CH3
H2 H2
1 C 3 CH 5 C 7 CH2
H3C 2 CH 4 C 6 C 8
H2 H2

CH2
H3C
 Alkanes - Nomenclature

1. Find the parent carbon chain and add the suffix.

Note that it does not matter if the chain is straight or it bends.

 Alkanes - Nomenclature
Also note that if there are two chains of equal length, pick the chain
with more substituents.
In the following example, two different chains in the same alkane
have seven C atoms.
We circle the longest continuous chain as shown in the diagram on the
left, since this results in the greater number of substituents.
 Alkanes - Nomenclature

2. Number the atoms in the carbon chain to give the first substituent
the lowest number.
 Alkanes - Nomenclature

If the first substituent is the same distance from both ends, number
the chain to give the second substituent the lower number.
 Alkanes - Nomenclature

When numbering a carbon chain results in the same numbers from

either end of the chain, assign the lower number alphabetically to the
first substituent.
 Alkanes - Nomenclature
3. Name and number the substituents.
• Name the substituents as alkyl groups.
• Every carbon belongs to either the longest chain or a substituent,
NOT both.
• Each substituent needs its own number
• If two or more identical substituents are bonded to the longest chain,
use prefixes to indicate how many: di- for two groups, tri- for three
groups, tetra- for four groups, and so forth.
 Alkanes - Nomenclature
4. Combine substituent names and numbers + parent and suffix.
• Precede the name of the parent by the names of the substituents.
• Alphabetize the names of the substituents, ignoring all prefixes except iso,
as in isopropyl and isobutyl.
• Precede the name of each substituent by the number that indicates its
location.
• Separate numbers by commas and separate numbers from letters by
hyphens. The name of an alkane is a single word, with no spaces after
hyphens and commas.
 Name the following alkane:

CH3
H2 H2 H2
C CH C C
H3C CH CH C CH3
H2

CH2 CH3
H2C

CH3
 5-methyl

4-ethyl
CH3
H2 H2 H2
C CH 6 C 8 C 10
4 5 7 9
H3C CH CH C CH3
H2
3 CH2 CH3
H2C 2

13
CH 6-methyl

4-ethyl-5,6-dimethyldecane
Write the formula for 3-ethylpentane

H2 H2
1 C 3 C 5
H3C 2 CH 4 CH3

CH2
H3C
Write the formula for 2,2,4-trimethylpentane

CH3 CH3

1 C CH 5
2 3 4
H3C C CH3
H2
CH3
Name the following molecules.
Cycloalkanes
We have discussed open-chained compounds up to this
point

Most organic compounds contain rings of carbon atoms

- Prostaglandins

- Steroids
Cyclic molecules are commonly
encountered in all classes of
biomolecules:
- Proteins
- Lipids
- Carbohydrates
- Nucleic acids
 Cycloalkanes
• Saturated cyclic hydrocarbons
• Have the formula CnH2n
• Their names are formed by adding
the prefix cyclo- to the name of the
alkane with the same number of
carbon atoms.
Cycloalkanes
Figure 19.11 Ball-and-stick models
illustrating cyclopropane, hexane, and
cyclohexane. In cyclopropane, all the
carbon atoms are in one plane (bond angles
= 60°). The cyclohexane molecule is
puckered (as shown in the chair
conformation) with bond angles at 109.5°.
 Naming Cycloalkanes

• Substituted cycloalkanes are named by

identifying and numbering the location of the
substituent(s) on the carbon ring, followed by
the name of the parent alkane.

CH3

methylcyclohexane
 Naming Cycloalkanes

• When a cycloalkane has two or more

substituted groups, the ring is
numbered (clockwise or
counterclockwise) to give the location
of the substituted groups the smallest
numbers.
 Naming Cycloalkanes
CH3
CH3 H3C CH3

1,1-dimethylcyclohexane 1,3-dimethylcyclohexane
CH3 CH3

CH3 H3C
1,2-dimethylcyclohexane 1,4-dimethylcyclohexane
 Naming Cycloalkanes
Cycloalkanes are named by using similar rules, but the prefix
cyclo- immediately precedes the name of the parent.

1. Find the parent cycloalkane.

 Naming Cycloalkanes
2. Name and number the substituents. No number is needed to
indicate the location of a single substituent.

For rings with more than one substituent, begin numbering at one
substituent and proceed around the ring to give the second
substituent the lowest number.
 Naming Cycloalkanes
With two different substituents, number the ring to assign the lower
number to the substituents alphabetically.

Note the special case of an alkane composed of both a ring and a long
chain. If the number of carbons in the ring is greater than or equal to
the number of carbons in the longest chain, the compound is named
as a cycloalkane.
Naming Cycloalkanes
Naming Cycloalkanes
Naming Cycloalkanes
Name the following molecules.
122