Mulungushi University

- Pursuing the frontiers of

knowledge

Organic Chemistry
Francis Kayamba

School Of Science, Engineering

and Technology

1
 Outline
• Elemental composition and
• Classification of organic compounds
 Hydrocarbons are the simplest
organic compounds
• Contain only C and H
• Simplest is CH4 (natural gas)
• Intermediate C8H18 (petroleum)
• Synthetic polymers contain thousands of
atoms
Classifying Organic Compounds
Organic
OrganicCompounds
Compounds

Hydrocarbons
Hydrocarbons Functionalized
Functionalized
Hydrocarbons
Hydrocarbons

Alkanes
Alkanes Alkenes
Alkenes Alkynes
Alkynes
CCnHH2n+2 CCnHH2n CCnHH2n−2. .
n 2n+2 n 2n n 2n−2
 Hydrocarbons
Hydrocarbons

Aliphatic
Aliphatic Aromatic
Aromatic
 Hydrocarbons
Hydrocarbons

Aliphatic
Aliphatic Aromatic
Aromatic

Alkanes
Alkanes Alkenes Alkynes
Alkenes Alkynes
 Hydrocarbons
Hydrocarbons

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

Alkanes H C C H
Alkanes

H H
 Hydrocarbons
Hydrocarbons

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

C C
Alkenes
Alkenes
H H
 Hydrocarbons
Hydrocarbons

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

Alkynes
Alkynes

HC CH
 Hydrocarbons
Hydrocarbons

The most common

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

H H

H H

H
 Representing molecules
• Molecular formula
 Shows atoms in the molecule
• Structural formula
 Expanded (Lewis)
 Shows how the atoms are all connected

 Condensed and
 Skeletal structural formula
 Simplified representation of connections
 Alkanes
• All bonds are single
• Saturated
• No new bonds can be added
• General formula CnH2n+2
 Alkanes
• The simplest homologous series is the alkanes.
Their names all end in –ane.
• Alkanes progressively differ by - CH2 - units.
Such a series of compounds is said to be
homologous.
A Homologous Series is a group of organic
chemical compounds, usually listed in order of
increasing size,
that have a similar structure (and hence also
similar properties) and whose structures differ only
by the number of CH2 units in the main carbon
chain.
Homologous Series of alkanes
Name of Series General chemical formula*

Alkanes CnH2n+2
Alkenes CnH2n
Alkynes CnH2n-2
1-bromoalkanes CnH2n+1Br
(e.g. of Haloalkanes)
1-alcohols CnH2n+1OH
(e.g. of Alcohols) = CnH2n+2O
Aldehydes CnH2nO
Carboxylic Acids CnH2nO2
Acid Chlorides CnH2n-1OCl
Amines CnH2n+1NH2
= CnH2n+3N
Amides CnH2n-1ONH2
= CnH2n+1ON
Nitriles CnH2n-3N
 Alkanes
• Lower alkanes with one to four carbons (C1 – C2) are
generally gases while alkanes containing five to ten
carbons (C5 – C10) are liquids
• Alkanes can also exist as cyclic hydrocarbons called
cycloalkanes. Cycloalkanes have a general formula
Cn – C2n the smallest one being cyclopropane for
which n=3.
 Alkanes
The alkanes have many uses:
•methane – (natural gas) cooking, heating
•propane – used in gas cylinders for BBQ
etc
•octane – used in petrol for cars
 Alkanes
Lewis structure
 Hydrocarbon Presentations
• Consider Hexane, Molecular Formulae C6H14

Realize that all the drawings

represent the exact same
molecule.....Hexane.
Condensed and skeletal
structures are just shorthand
versions of Lewis structures
 Hydrocarbon Presentations

• Cyclopentane , Molecular Formulae C5H10

Remember that with skeletal structures, hydrogens’ are

omitted for clarity. Thus, you need to sure you can
identify these situations to understand the bonding of
each carbon in a given molecule
Summary of Types
 Example
• Write the molecular formula and structural
formulae (Expanded- Lewis, condensed and
skeletal) for:
a) 2-Methylpropane
b) Butane
 Nomenclature
Nomenclature

Common
Commonnames
names IUPAC
IUPAC
(trivial)
(trivial) Systematic
Systematic
Non
Non- -systematic
systematic
 Nomenclature
Nomenclature

A nomenclature system
useful for naming simple
Common organic molecules. It often
Commonnames
names
Non-
fails for more complex
Non-systematic
systematic
molecules in which case
systematic or (better yet)
IUPAC nomenclature is
preferable.
 Nomenclature
Nomenclature

This is a systematic
method of naming
organic chemical
compounds as IUPAC
IUPAC
recommended by the
Systematic
Systematic
International Union of
Pure and Applied
Chemistry (IUPAC).
 NOMENCLATURE
1. Common system
a. Works best for low molecular weight hydrocarbons
b. Steps to give a hydrocarbon a common name:
1. Count the total number of carbon atoms in the
molecule.
2. Use the Latin root from the following slide that
corresponds to the number of carbon atoms followed
by the suffix “ane”.
3. Unbranched hydrocarbons use the prefix normal, or
n-,
4. Branched hydrocarbons use specific prefixes, as
shown on a subsequent slide
 NOMENCLATURE
Common system Examples

1. Give a name for the following compound

H H H
H C C C H
H H H

Step #1, count the number of carbons and write down the memorized Latin name
for that number (next slide)
Step #2, since this structure fits the alkane general formula, use the “ane” suffix

propane Alkane suffix

Three carbon Latin root

 Examples
Latin Latin
Hydrocarbon Hydrocarbon H H H H
H
Roots Roots H C C
H H H H
C C

Number of Latin Number of Latin n-butane

Carbons Root Carbons Root H H
C H
1 meth 12 dodec H H
2 eth 13 tridec H C C C H
3 prop 14 tetradec H H H
4 but 15 pentadec isobutane
5 pent 16 hexadec
6 hex 17 heptadec
7 hept 18 octadec
8 oct 19 nonadec
9 non 20 eicos
10 dec 21 unicos
11 undec 22 doicos
Nonsystematic names; Common names
Nonsystematic names; Common names
2. Systematic System of Nomenclature
(IUPAC)
• International Union of Pure and Applied Chemistry
(IUPAC) has established the system
• We will refer to names derived from this system as
systematic nomenclature or IUPAC nomenclature
(shown in blue)
• Additional names such as isopentane and neopentane
are common names (shown in red)
• A compound may have more than one name BUT a
name must specify only one compound
Alkanes - (IUPAC) Nomenclature

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.
Alkanes - Nomenclature

Parent – Longest straight carbon chain

Alkanes - Nomenclature

Suffix – Our first functional group is alkane, so the suffix is –ane

For later functional groups we will drop the –ane root suffix for others
Alkane chain # Carbons Name
CH4 1 methane
CH3CH3 2 ethane
CH3CH2CH3 3 propane
CH3CH2CH2CH3 4 butane
CH3CH2CH2CH2CH3 5 pentane
CH3CH2CH2CH2CH2CH3 6 hexane
CH3CH2CH2CH2CH2CH2CH3 7 heptane
CH3CH2CH2CH2CH2CH2CH2CH3 8 octane
CH3CH2CH2CH2CH2CH2CH2CH2CH3 9 nonane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 10 decane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 11 undecane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 12 dodecane
Alkanes - Nomenclature

Prefix – Our substituents will be branches in the alkane structure

A branch is another alkane minus one hydrogen – an alkyl group
Example – if CH3- is a branch on a longer chain:

CH3- is CH4 minus 1 hydrogen

Since it is a side chain it will replace the –ane suffix with –yl

CH3- is a methyl group

We can also abbreviate this group as Me-

Alkanes - Nomenclature
Prefixes -
Alkyl group Structure IUPAC name Abbreviation

CH3- CH3- methyl Me-

CH3CH2- ethyl Et-

CH3CH2CH2- n-propyl n-Pr

CH3CHCH3 isopropyl or i-propyl i-Pr

CH3CH2CH2CH2- n-butyl n-Bu

CH3CH2CHCH3 sec-butyl s-Bu

(CH3)2CHCH2- isobutyl or i-butyl i-Bu

(CH3)3C- tert-butyl or t-butyl t-Bu

C6H5- phenyl Ph

• Typically any unspecified alkyl group is represented as R-

 IUPAC Rules for Naming Hydrocarbons
1. Choose the correct ending - suffix: -ane, -ene, or -yne
2. Determine the longest carbon chain. Where a double or triple
bond is present, choose the longest chain that includes this bond.
If there is a cyclic structure present, the longest chain starts and
stops within the cyclic structure.
3. Assign numbers to each C of the parent chain. For alkenes and
alkynes the first carbon of the multiple bond should have the
smallest number. For alkanes the first branch (or first point of
difference) should have the lowest #. Carbons in a multiple bond
must be numbered consecutively.
4. Attach a prefix that corresponds to the number of carbons in the
parent chain. Add cyclo- to the prefix if it is a cyclic structure.
 IUPAC Rules for Naming Hydrocarbons
5. Determine the correct name for each branch
(“alkyl” groups include methyl, ethyl, propyl, etc.)
6. Attach the name of the branches alphabetically,
along with their carbon position, to the front of the
parent chain name. Separate numbers from
letters with hyphens (e.g. 4-ethyl-2-methyldecane)
7. When two or more branches are identical, use
prefixes (di-, tri-, etc.) (e.g. 2,4-dimethylhexane).
Numbers are separated with commas. Prefixes
are ignored when determining alphabetical order.
(e.g. 2,3,5-trimethyl-4-propylheptane)
8. When identical groups are on the same carbon,
repeat the number of this carbon in the name.
(e.g. 2,2-dimethylhexane)
 Naming Side Chains
Example: use the IUPAC rules to name the
following structure
CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 1: choose the correct ending

ene
 Naming Side Chains

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 2: determine the longest carbon chain

ene
 Naming Side Chains

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 3: Assign numbers to each carbon

ene
 Naming Side Chains

CH2 CH2 CH3

1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3

Rule 3: Assign numbers to each carbon

ene
 Naming Side Chains

CH2 CH2 CH3

1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3

Rule 4: attach prefix (according to # of Cs)

1-hexene
ene
 Naming Side Chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 5: Determine name for side chains
1-hexene
 Naming Side Chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 6: attach name of branches alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
 Naming Side Chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 7,8: group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
 Naming Side Chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 7,8: group similar branches
2-ethyl-4,4-dimethyl-1-hexene
CH3 CH CH2 CH3 CH3
propene CH3 CH CH C CH3

CH3 CH CH CH3
2,4-dimethyl-2-pentene
2-butene

CH C CH2 CH3
1-butyne
 CH3 CH3

CH2 CH C CH2 CH3 CH3 C CH CH2

CH3 CH2 CH3

a) 3,3-dimethyl-1-pentene b) same

CH 3 CH 3

CH 3 C C CH CH CH 2

CH 2 CH 3
c) 5-ethyl-4-methyl-2-heptyne For more lessons, visit
www.chalkbored.com
Alkanes - Nomenclature
1. Choose the correct endng, the suffix. - ane

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.
 Examples

5 4 3 2 1
CH3 CH2 CH2 CH CH3 parent alkane

CH3
alkyl group

2-methylpentane
 Examples

1 2 3 4
CH3 CH CH CH3
CH3 CH3
2,3-dimethylbutane

CH3
4 3 2 1
CH3 CH2 C CH3
CH3
2,2-dimethylbutane
 Examples

CH3 CH3
7 6 5 3 1
CH3 CH CH2 CH CH CH CH3
4 2
CH3 CH3

2,3,4,6-tetramethylheptane

Note: Number the chain so that the substituents get the lowest
possible numbers.
 Examples

2 1
CH2 CH3

CH3 CH CH2 CH2 CH3

3 4 5 6

3-methylhexane

Caution: Be careful to choose the longest chain as the parent alkane.

 Examples

CH2 CH3
8 7 6 5 4 3 2 1
CH3 CH2 CH2 CH2 C CH CH CH3
CH3 Cl CH3

3-chloro-4-ethyl-2,4-dimethyloctane

Note: Substituents are listed in alphabetical order.

 Draw the Compounds
• 3-ethylpentane
1 2 3 4 5
CH3 CH2 CH CH2 CH3
CH2 CH3

• 2,2,4-trimethylpentane
CH3
1 2 3 4 5
CH3 C CH2 CH2 CH3
CH3 CH3
 CH3
CH CH2 CH2 CH3
CH3 CH2 CH CH2
CH3
Name the structures below
Name

H3C CH2 H3C CH2 CH2 CH3

CH CH3 CH CH CH2 CH3
H2C CH2
H3C CH
CH3
CH3

CH3 CH3 CH3

CH3 CH2 CH CH CH CH2 CH CH3
CH2 CH3
 Draw the Draw the structures
structures below thebelow
structures below

3-ethyl-2-methylpentane

3-ethyl-1,5,5-trimethylcyclohexene
 Line Structures
A quicker way to write structures'
CH3 CH3
H3C CH CH CH2 CH2 CH CH3 (Condensed Structure)
CH2CH3
ethyl methyl

(A line structure of the above

condensed structure)

methyl
 Nomenclature of Cycloalkanes
 Cycloalkanes generally are shown as skeletal
structures

© Prentice Hall 2001 Chapter 2 67

 Nomenclature of Cycloalkanes
1. Ring is the parent hydrocarbon unless the
alkyl substituent has more carbons; in that
case the substituent becomes the parent
hydrocarbon
If only one substituent, no need to give it a
number

© Prentice Hall 2001 Chapter 2 68

 Nomenclature of Cycloalkanes
2. If the ring has 2 substituents, list in
alphabetical order and give number 1 to
first named group

© Prentice Hall 2001 Chapter 2 69

 Nomenclature of Cycloalkanes
3. If there is more than one substituent, list in
alphabetical order; one substituent is given
the position number 1; number either
clockwise or counterclockwise - lowest
numbers

© Prentice Hall 2001 Chapter 2 70

 HOW TO Name a Cycloalkane Using the IUPAC System

Cycloalkanes are named by using similar rules, but the prefix ‘cyclo-’
immediately precedes the name of the parent.

Step [1] Find the parent cycloalkane.

71
 Numbering Substituents in Cycloalkanes
Step [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.

72
Naming Cycloalkane Substituents Alphabetically

With two different substituents, number the ring to assign the lower
number to the substituents alphabetically.

73
 Naming Alkanes versus Cycloalkanes
• 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.
• If there are more carbons in the chain, the compound is named as an
alkane.

Figure 4.2

74
 Examples of Naming Cycloalkanes

Figure 4.3

75
Alkenes - Nomenclature

• Compounds with two double bonds are named as dienes by

changing the “-ane” ending of the parent alkane to the suffix “-
adiene”.
• Compounds with three double bonds are named as trienes, and
so forth.
• In naming cycloalkenes, the double bond is located between C1
and C2, and the “1” is usually omitted in the name.
• The ring is numbered clockwise or counterclockwise to give the
first substituent the lower number.

76
Alkynes - Nomenclature

• Alkynes are named in the same general way that alkenes are
named.

• In the IUPAC system, change the –ane ending of the parent

alkane name to the suffix –yne.

• Choose the longest continuous chain that contains both atoms

of the triple bond and number the chain to give the triple bond
the lower number.

77
Alkynes - Nomenclature

• Compounds with two triple bonds are named as diynes, those

with three are named as triynes and so forth.
• Compounds with both a double and triple bond are named as
enynes.
• The chain is numbered to give the first site of unsaturation
(either C=C or CC) the lower number.

78
Other Functional Groups - Nomenclature
The IUPAC rules for all other functional groups will differ only by the
following:
1.Suffix will change to reflect functional group
2.Some functional groups have priority over others

For now: Alcohol > Alkyne > Alkene > alkane=alkyl halide
3.The longest chain must contain the suffix functional group – even if not
the longest chain overall
4.Numbering gives this functional group the lowest number – even if there
are other groups that would be lower
5.If an alkene has stereochemistry, it must be specified in the prefix
Alkyl Halides - Nomenclature