Lecture notes SL

By dott. Anoosha Qaisar

 Table of contents

1. Types of formulas
2. Functional groups
3. homologous series
4. Nomenclature of organic compounds
5. structural isomerism
6. Classification of Functional groups
STRUCTURE 3. CLASSIFICATION OF MATTER

STRUCTURE 3.2—FUNCTIONAL GROUPS: CLASSIFICATION OF

ORGANIC COMPOUNDS

Guiding question: How does the classification of organic molecules help us to

predict their properties?
S 3.2.1 FORMULAS OF ORGANIC COMPOUNDS
Learning outcomes
After studying this topic you should be able to:
Understand: Apply knowledge to:

● Organic compounds can be ● Identify different formulas and

represented by different types of interconvert molecular, skeletal
formulas. These include and structural formulas.
empirical, molecular, structural Construct 3D models (real or
(full and condensed), virtual) of organic molecules
stereochemical and skeletal.
Clarification Note: Stereochemical formulas are not expected to be
drawn, except where specifically indicated
TYPES OF CHEMICAL FORMULAS
● Empirical Formula: a represents the simplest ratio of atoms present in a
molecule.
● Molecular Formula: describes the actual number of atoms present in the
molecule.
Example
Glucose
● Empirical Formula CH2O Molecular Formula C6H12O6

Both these types of formula offer you little or no information about the
possible structures of larger, more complex molecules.
STRUCTURE FORMULA:
Describe the structure of a compound.
There are three types of structural formula:

● Full structural formulas are two-dimensional representations showing all the

atoms and bonds, and their positions relative to one another in a compound.

● In a condensed structural formula, all the atoms and their relative positions are
shown, but some or all the bonds are omitted.

● A skeletal formula is the most basic representation of the structural formula,

where the carbon and hydrogen atoms are not shown but the end of each line and
each vertex represents a carbon atom.
TYPES OF CHEMICAL FORMULAS
PRACTICE
 STEREOCHEMICAL FORMULA
● Attempts to show the positions of atoms in three dimensions.
○ A bond sticking out of the front of the page is represented by a solid
triangular wedge.
○ A bond sticking out of the back of the page is dotted line.
○ Four bonds are tetrahedral with bond angles of 109.5°.
○ Three bonds are trigonal planar with 120°.
HTTPS://MOLVIEW.ORG/
S 3.2.2 FUNCTIONAL GROUPS
Learning outcomes
After studying this topic you should be able to:
Understand: Apply knowledge to:
Functional groups give characteristic Identify the following functional
physical and chemical properties to a groups by name and structure:
compound. Organic compounds are halogeno, hydroxyl, carbonyl,
divided into classes according to the carboxyl, alkoxy, amino, amido,
functional groups present in their
ester, phenyl.
molecules

Clarification Note: The terms “saturated” and “unsaturated”

should be included.
 FUNCTIONAL GROUP
● A functional group is an atom, or a group of atoms, that gives organic
compounds their physical and chemical characteristics.
● Functional groups give characteristic physical and chemical properties to
a compound.
● Organic Compound = Alkyl group + Functional group
● Example
Alcohol = Alkyl group + Hydroxyl Group
● Ethanol = Ethyl + Hydroxyl group
C2H5OH = C2H5 + OH
 Saturated And Unsaturated Hydrocarbons
● In a saturated compound, all the carbon-carbon bonds are single. The
simplest example of a saturated hydrocarbon is methane, CH4, a member
of the alkane family.
Ethane- another example of saturated hydrocarbon

● The primary carbon chain in an unsaturated hydrocarbon must contain

one or more double or triple carbon-carbon bonds. Hydrocarbons with
carbon -carbon double bonds are called alkenes.
Ethene- an example of unsaturated hydrocrabons
S 3.2.3/4 HOMOLOGOUS SERIES
Learning outcomes
After studying this topic you should be able to:
Understand: Apply knowledge to:

● A homologous series is a family of ● Identify the following homologous

series: alkanes, alkenes, alkynes,
compounds in which successive halogenoalkanes, alcohols, aldehydes,
members differ by a common ketones, carboxylic acids, ethers,
structural unit, typically CH2. Each amines, amides and esters.
homologous series can be described ● Describe and explain the trend in
by a general formula melting and boiling points of members
of a homologous series.
● Successive members of a
homologous series show a trend in
physical properties
 HOMOLOGOUS SERIES

●Definition – family of organic compounds which possesses

certain common features.
○Successive members differ by a –CH2 group.
○Members of a series can be represented by the same general
formula.
○Members show a gradation in physical properties.
○Members have similar chemical properties.
MEMBERS DIFFER BY –CH2
●In a homologous series, as you change from one
member to the next, the molecular mass increases by
a fixed amount.
●This fixed amount is due to the addition of successive
–CH2 groups.
●When you go from propane to butane, what changed?
○ You added one carbon to the series along with two
hydrogen atoms.
●This is typical of each homologous series.
 MEMBERS REPRESENTED BY SAME
GENERAL FORMULA
●Alkanes and alkenes are represented by the formulas CnH2n+2 and
CnH2n respectively.

●A functional group is a small group of atoms attached to a carbon

atom giving the compound characteristic properties.

●Functional groups are shown in the general formulas.

○ Alcohols are represented by CnH2n+1OH or ROH where “R” is the parent hydrocarbon
abbreviation.
 Members Show A Gradation Of Physical
Properties
●As successive members of a series differ by a –CH2
group, they have successively longer chains.
●There is a gradual trend in the change of physical
properties due to this change in molar mass.
●Boiling point, density and viscosity are physical
properties with predictable trends in homologous series.
Members Show Similar Chemical Properties.

●Since members of a series have the same functional group,

their members show similar chemical reactivity.

●If we know the characteristic reactions of a functional group,

we can predict the properties of all members of a series.
EXAMPLES OF HOMOLOGOUS SERIES
Alcohol
Alkene CH3OH Methanol
C2H4 Ethene C2H5OH Ethanol
C3H6 Propene C3H7OH Propanol

C4H8 Butene C4H9OH Butanol

C5H10 Pentene C5H11OH Pentanol

C6H12 Hexene C6H13OH Hexanol

BOILING POINT TRENDS

●The boiling point is affected by the length of the carbon

chain.

●Boiling point increases with increasing carbon number.

●This is caused by the increased number of temporary
dipoles causing stronger van der Waal’s forces between
molecules as their size increases.
● The first four alkanes are gases at room temperature
followed by the next four alkanes existing as liquids at
room temp.

● Methane has a boiling pt of -164°C and octane 125°C.

● The increase is not linear, but steeper near the
beginning because the smaller molecules are more
affected by the addition of a –CH2.
Number of
carbon
atoms and
boiling
points
S 3.2.5 NOMENCLATURE
Learning outcomes
After studying this topic you should be able to:
Understand: Apply knowledge to:
“IUPAC nomenclature” refers to a Apply IUPAC nomenclature to
saturated or mono-unsaturated
set of rules used by the
compounds that have up to six
International Union of Pure and carbon atoms in the parent chain
Applied Chemistry to apply and contain one type of the
systematic names to organic and following functional groups:
inorganic compounds. halogeno, hydroxyl, carbonyl,
carboxyl
Clarification Note: Include straight-chain and branched-chain
isomers.
NOMENCLATURE
SYSTEM OF NAMING
 Naming Organic
Compounds
● Originally compounds were named based on their source
or use
● Many organic compounds were given common names
which are still in use
● However many ambiguities resulted
● With the large number of organic compounds, a method
for systematically naming them is very important
 IUPAC Names

● The International Union of Pure and Applied Chemists

(IUPAC) developed a system for naming organic compounds.

● This system eliminated many of the ambiguities that plagued

earlier naming systems

● Common names for many substances are still widely used

Naming Hydrocarbons using the
IUPAC System
A series of prefixes are used to designate the
number of carbon atoms in a carbon chain

meth 1C hex 6C
eth 2C hept 7C
prop 3C oct 8C
but 4C non 9C
pent 5C dec 10 C
 Naming Alkanes
● For straight chain hydrocarbons. The prefix indicates
the number of carbon atoms.

● The suffix ane is added to designate that the

compound is an alkane

47
 Naming Alkanes with
●
branched chains
For branched chain hydrocarbons, identify the longest
consecutive (straight) chain first. Then name the side
chains or branches.

● The name of the branches end in “yl” and go before the

name of the straight chain

-methylpropane dimethyl propane

methyl butane

https://youtu.be/Hur2jQ-rahk?si=tY
qtlSo-NKKVLYto
 H
2-methyl
H C H

H H H H H
H C
H
C C
H
C
H
C
H
C
H
H
Hexane
H C H
H
2-methyl
2-methyl, 2-methyl hexane
Sounds redundant
2,2 dimethyl hexane
PRACTICE

2-methyl hexane

2,3-Dimethyl hexane
IS YOUR ARM SORE YET?

●Are you sick to death of

writing all those carbons?

●Even worse, are you sick of

writing all those Hydrogens?

●How about this…

SHORTHAND NOTATION

Keep in mind that we have been ignoring the

hydrogens for a long time.

Our names have been based entirely on the

positioning of the carbons.

So lets now ignore the hydrogens

completely!
IS IT THAT EASY?
 Alkenes
● Alkenes have one (or more) carbon to carbon
double bonds
● When there are 4 or more carbon atoms in a chain,
the location of the double bond is indicated by a
number.
● Numbering the location of the double bond(s) takes
precedence over the location of side chains

but-1-ene but-2-ene 2-methylpropene

 H
H H H H H
H C
H
C C C
H
C C
H
H hex-2-ene
H

H H H H
H C
H
C C C H
but-1-ene
H

H C H

H H H H
H C C C C C H 3 methyl pent-1-ene
H H H
HOW ABOUT IN SHORTHAND?

3-methylpent-1-ene,

Notice the two lines

pent-2-ene
means the double bond
is there!

2,3-dimethylbut-2-ene,
PRACTICE!

Methyl propene

2,4-dimethylpent-2-ene

3-ethyl-2,4,4-trimethylpent-1-ene
GEOMETRIC ISOMERS IN
ALKENES
● A cis isomer is one in which the substituents are
on the same side of the C=C

cis-but-2-ene

A trans isomer is one in which the substituents are on

the opposite sides of the C=C

trans-but-2-ene

58
CIS ISOMERS HAVE HIGHER BOILING
POINT THAN TRANS.
 trans pent-2-ene

2,3-dimethylbut-2-ene

does not have geometrical isomers because there

are two identical groups attached to the same
carbon of the double bond.
 Alkynes

● Alkynes have one (or more) carbon to carbon triple bonds

● Since there are fewer hydrogen atoms in alkynes as a result of the

triple bond, alkynes like alkenes are referred to as unsaturated.

61
 Alkyne Structures
● Like alkanes and alkenes, alkynes can have branched
or consecutive chains. In the larger alkenes there are
also multiple locations for the C=C. Multiple structural
isomers are possible. The branch cannot originate on
one of the carbons making up the triple bond

Straight chain. The Straight chain. The Branched chain. The triple bond
triple bond is between triple bond is between can occur in one of the branches
the first and second the second and third but branches cannot be attached
carbon carbon to any carbon in the triple bond
 PRACTICE
● Draw the structure of the followings
3-Methylpent-1-yne 4,4-Dimethylhex-2-yne
PRACTICE
THIS ONE

● Pentyne
HEAD-TO-HEAD NAMING
Draw a hydrocarbon molecule on a sheet.
Have a friend draw a hydrocarbon
molecule on their sheet. Exchange papers
and see who can correctly name the other
persons hydrocarbon first. As always, no
wagering please.

For more lessons, visit

www.chalkbored.com
HALOGENOALKANE

●Fluorides, Chlorides,
Bromides, and Iodides
attached to Alkyl group

●Simply name the molecule as

normal but add the prefix
Fluoro, Chloro, Bromo, or
Iodo as necessary
HALOGENOALKANE
1-bromopropane prefixes = “fluoro,
chloro, bromo,
iodo”
2 chlorobutane

1,2 diiodoethane

cis 1,2difluroethene

Trans 1,2 difluoroethene

1,1,2 trifluorothene
68
TOK CONNECTION
Functional Groups
● Halogenoalkanes ● R-F, R-Cl, R-Br, R-I
● Alcohols ● R-OH
● Ethers ● R-O-R
● Aldehydes ● R-COH
● Ketones ● R-CO-R
● Carboxylic Acids ● R-COOH
● Esters ● R-COO-R
● Amines ● R-NH2
NAMING COMPOUNDS WITH
FUNCTIONAL GROUPS
Various functional groups have unique suffixes that designate the
functional group.
The functional group takes precedence in numbering the carbon
chain.
Branches to the carbon chain are named in the usual manner.
ALCOHOLS

●R-OH
●Name like normal except add
an –ol suffix
ALCOHOLS

Propan-1-ol
Suffix = “ol”

Propan-2-ol

2-methylpropan-2-ol

75
ALCOHOLS
ETHERS

●R-O-R
●Name two “R” groups with –yl
endings

●End name in ether

ETHERS
Suffix = “oxy”on first branch

Ethoxyethane
(diethyl ether)

Ethoxybutane
(ethyl butyl
ether)

78
ETHERS
ALDEHYDE

●R-CHO
●This is a carbon to oxygen
double bond with a hydrogen
at the end.

●Name as normal except use

a “-al” suffix
ALDEHYDES AND ALKANALS

Suffix = “al”
Propanal
Note that the aldeyhde
group is always on an
end carbon or carbon
1

81
 H H H O

H C C C C H butanal
H H H

H H Cl H O

H C C C C C H 3,3 dichloropentanal
H H Cl H
KETONES OR ALKANONES
Suffix = “one”

Propanone
(also known as acetone)

Butanone
(also known as ethyl methyl ketone)

Pentan-2-one
(note the number is necessary
Because the C=O could be on carbon
2 or carbon 3)

83
 H O H H H

H C C C C C H pentan-2-one
H H H H

H H H H O H

H C C C C C C H hexan-2-one
H H H H H
CARBOXYLIC ACIDS

●R-COOH or R-CO2H
●This is a carbon to oxygen
double bond with the same
carbon single-bonded to an
OH group.
●Name as normal except give
it the suffix “-anoic acid”.
CARBOXYLIC ACIDS

Suffix = “oic”

Butanoic acid

Note that the acid group

(called a “carboxyl”) is
always on an end carbon
or carbon 1

86
 H H H O

H C C C C OH Butanoic acid
H H H

O H H

HO C C C F 3-Fluoropropanoic acid
H H
ESTERS

● R-COO-R
● This is a carbon to oxygen double
bond with a carbon to oxygen
single bonded to another single
bonded carbon

● Name by given secondary branch

“-yl” suffix and main branch
“-anoate” suffix.
 Esters
Suffix = “oate”

Ethyl butanoate

Butyl ethanoate
There are two branches. The
branch with the carbonyl gets the
suffix

89
Main Branch Secondary
Branch
H H H H O H

H C C C C C O C H

H H H H H

pentanoate methyl

Methyl Pentanoate
 H H O H H H H

H C C C O C C C C H Butyl propanoate
H H H H H H

H O H H H H H

H C O C C C C C C H Methyl hexanoate
H H H H H H
AMINES

●R-NH2
●Name the “R” group or
groups with “-yl” endings

●Add the word “amine”

AMINES Not directly
included in syllabus
Suffix = “amine”
Or prefix = “amino”

Propylamine or 1-aminopropane

2-propylamine or 2-aminopropane

2-methyl-2-propylamine or

2-methyl -2- aminopropane

93
 H H

H C N Methyl amine
H H

H H

H C N

H C H Dimethyl amine
H H
AMIDES Not directly
included in syllabus
Suffix = “amide”

butanamide

Note that the amide group is

always on an end carbon or
carbon 1
 R Cl R OH R O R
Halide Alcohol Ether

O O O

R C H R C R R C OH
Aldehyde Ketone Carboxylic Acid

R C O R R NH2
Ester Amine
SUMMARY
S 3.2.6 ISOMERS
Learning outcomes
After studying this topic you should be able to:
Understand: Apply knowledge to:

● Structural isomers are molecules ● Recognize isomers, including

that have the same molecular branched, straight-chain,
formula but different position and functional group
connectivities. isomers

Clarification Note: Primary, secondary and tertiary alcohols,

halogenoalkanes and amines should be included.
STRUCTURAL ISOMERS

● Structural isomers are different compounds with the same molecular

formula but different arrangements of atoms
Butane C4H10
 STRUCTURAL ISOMERS- TYPES
Chain isomers Positional isomers Functional group isomers are
are structural are structural isomers structural isomers with the
isomers with where the position of atoms arranged differently
different lengths the functional group such that they have different
of carbon chains. changes functional groups.
CHAIN ISOMERS

● Chain isomers are structural isomers with different lengths of carbon

chains. For example, butane and methylpropane both have the
molecular formula C4H10. Butane is a straight-chain molecule because
it has no substituents on the carbon chain
TRY STRUCTURAL FORMULA FOR

● C5H12

● C5H10 ( hint one double)

POSITION ISOMERS
● Positional isomers are structural isomers where the position of the
functional group changes. Example C3H7OH, has two isomers
propan-1-ol and propan-2-ol
TRY STRUCTURAL FORMULA SHOWING
POSITION ISOMER IN THE FOLLOWING
● C4H7Cl

● C5H9NH2
FUNCTIONAL GROUP ISOMERS
● Functional group isomers are structural isomers with the atoms
arranged differently such that they have different functional groups.
For example, consider the molecular formula C2H6O.
TRY STRUCTURAL FORMULA SHOWING
FUNCTIONAL GROUP ISOMERISM IN THE
FOLLOWING
● C 3H 6O

● C 2H 4O 2
CLASSIFICATIONS
PRIMARY SECONDARY AND
TERTIARY
HALOGENOALKANES , ALCOHOLS AND AMINES
LEARNING OBJECTIVES

● Distinguish between primary secondary and tertiary Alcohols.

● Distinguish between primary secondary and tertiary halogenoalkanes.
● Distinguish between primary secondary and tertiary Amines.
CLASSIFICATIONS OF ALCOHOL

LEARNING OBJECTIVES
DISTINGUISH BETWEEN PRIMARY SECONDARY AND TERTIARY
ALCOHOLS
PRIMARY, SECONDARY AND TERTIARY
CARBON
● Primary = a carbon attached to only ONE other carbon
● Secondary = a carbon attached to only TWO other carbons
● Tertiary = a carbon attached to THREE other carbons
S3.2.6—Structural isomers are molecules that have the same molecular formula but different connectivities.
Recognize isomers, including branched, straight-chain, position and functional group isomers.

Primary, Secondary and Tertiary Compounds

Stability of benzene ring is due to delocalized electrons
PRIMARY ALCOHOLS
A primary alcohol has only one carbon atom attached
SECONDARY ALCOHOLS
A secondary alcohol has 2 carbon chains attached to the group on which
the –OH resides
TERTIARY ALCOHOLS
● Is cholesterol a primary, secondary or tertiary
alcohol?

● Secondary
CLASSIFICATION OF
HALOGENOALKANES

LEARNING OBJECTIVES

DISTINGUISH BETWEEN PRIMARY SECONDARY AND TERTIARY HALOGENOALKANES

PRIMARY HALOGENOALKANE

● In a primary (1°) halogenoalkane, the carbon which carries the

halogen atom is only attached to one other alkyl group.

● Some examples of primary halogenoalkanes include:

 SECONDARY HALOGENOALKANES

● In a secondary (2°) halogenoalkane, the carbon with the halogen

attached is joined directly to two other alkyl groups, which may be the
same or different.

● Examples:
 TERTIARY HALOGENOALKANES

● In a tertiary (3°) halogenoalkane, the carbon atom holding the halogen

is attached directly to three alkyl groups, which may be any
combination of same or different.

● Examples:
PRACTICE

●
 CLASSIFICATION OF AMINES

LEARNING OBJECTIVES
DISTINGUISH BETWEEN PRIMARY SECONDARY AND TERTIARY AMINES
PRIMARY AMINES
● In primary amines, only one of the hydrogen atoms in the ammonia molecule has
been replaced. That means that the formula of the primary amine will be RNH2
where "R" is an alkyl group.

● Examples include:
SECONDARY AMINES
● In a secondary amine, two of the hydrogens in an ammonia molecule have been
replaced by hydrocarbon groups. At this level, you are only likely to come across
simple ones where both of the hydrocarbon groups are alkyl groups and both are the
same.

● For example:
 TERTIARY AMINES
● In a tertiary amine, all of the hydrogens in an ammonia molecule have been
replaced by hydrocarbon groups. Again, you are only likely to come across simple
ones where all three of the hydrocarbon groups are alkyl groups and all three are
the same.

● The naming is similar to secondary amines. For example:

PRACTICE
Syllabus Guidance:

• The distinction between class names and functional group names needs to be made.
Eg for OH,hydroxyl is the functional group whereas alcohol is the class name.

• The following nomenclature should be covered:

– non-cyclic alkanes and halogenoalkanes up to halohexanes.
– alkenes up to hexene and alkynes up to hexyne.
– compounds up to six carbon atoms (in the basic chain for nomenclature purposes)
containing only one functional group: such as hydroxyl, carbonyl, carboxyl, alkenyl etc.