ORGANIC CHEMISTRY

10
 What is Organic Chemistry?

• This is the study of the compounds of carbon.

• Examples include carbohydrates, proteins, fuel,
alcohols, etc.
• Organic compounds are studied separately from the
compounds of other elements because organic
compounds are
– Important: food, medicine, fuel are all organic
– complex e.g. the DNA, Polymers
• Simple compounds of carbon like carbon dioxide,
sodium carbonate, etc are not regarded organic
compounds.
 HOMOLOGOUS SERIES
• Definition – family of organic compounds with the
same functional group that can be represented by
a general molecular formula. They share the
following properties:
– Successive members differ by a –CH2 group.
– Members show a gradation in physical properties due to
differences in sizes.
– Members have similar chemical properties as chemical
properties are determined by the functional group.
– Members of a series can be represented by the same
general molecular formula. E.g. CnH2n+2 (alkanes)
 Why different physical properties?
• Members show gradation in physical properties like
boiling point and melting point as size increases.
 Common homologous series

NAME GENERAL FORMULA FUNCTIONAL EXAMPLE

GROUP

Alkane C2H2n+2 -C- CH4, CH3CH3

Alkene CnH2n C=C CH2=CH2

Alkyne CnH2n-2 -C  C- HC  CH

Alkanol CnH2n+1OH -OH CH3CH2OH

Alkanoic acid CnH2n+1COOH -COOH CH3COOH

Alkanamide CnH2n+1CONH2 -CONH2 CH3CONH2

Alkyl CnH2n+1COOR -COOR CH3COOCH3


alkanoate
 Functional group
• This is an atom or small group of atoms on an organic
molecule that gives it characteristic properties.
– Alkane -C-
– Alkene -C=C-
– Alkyne -C C-
– Alcohol -OH
– Ether -O-
– Aldehyde -CHO
– Ketone -CO-
– Carboxylic acid -COOH
– Ester -COOR
– Halogenoalkane -C-X (X=halogen)
– Arene (Benzene)
– Amide -CONH2
– Amine -NH2
– Nitrile -C  N
Functional group
 Functional Group: C-C

• Alkanes are single bonded carbon chains.

• The suffix is –ane.
• Alkanes are saturated hydrocarbons.
• General formula: CnH2n+2
• Class – alkane
• Functional group – none
 Functional Group: C=C

• Alkenes have a double bonded carbon within the

chain. Unsaturated.
• The suffix is –ene.
• The molecule is named by using the smallest
numbered carbon that is part of the double bond.
but-1-ene
• General formula: CnH2n
• Class – alkene
• Functional group – alkenyl
• Alkynes have a triple bonded carbon within the
chain. Unsaturated.
• The suffix is –yne.
• The molecule is named by using the smallest
numbered carbon that is part of the double bond.
but-1-yne
• General formula: CnH2n-2
• Class – alkyne
• Functional group – alkynyl
 Functional Group: -OH

• Alcohols have the functional group –OH.

• The suffix is –anol.
– Examples are ethanol and propanol.
• The position of the functional group is
shown by a number between hyphens
inserted before the functional group ending.
– Propan-2-ol has the –OH group located on the
2nd carbon of the series.
• General formula: CnH2n+1OH
• Class – alcohol
• Functional group – hydroxyl
 Functional Group: R-O-R’
• Ethers have an oxygen in the chain between
two alkyl groups.
• The suffix is –oxyalkane.
– Examples are methoxyethane and ethoxypropane.
• General formula: R-O-R’
• Class – ether
• Functional group – ether
 Functional Group: -C=O
H
• Aldehydes have the above functional group with a
double bonded oxygen on the carbon along with a
hydrogen.
• The carbon with the double bonded oxygen is used in
the stem name.
• The suffix or ending is –anal.
– C2H5CHO is propanal. (Notice the C in the CHO is
part of the carbons counted in the stem.)
• General formula: R-CHO
• Class – aldehyde
• Functional group – aldehyde or carbonyl
 Functional Group: R-C=O
R’
• Ketones have a double bonded oxygen on an interior
carbon. The R and R’ represent the sides of the
carbon chain.
• The ending or suffix is –anone.
– CH3COCH3 is propanone.
• General formula: R-CO-R’
• Class – ketone
• Functional group – carbonyl
 Functional Group: -C=O
O-H
• Carboxylic Acids have a double bonded oxygen
and an –OH group attached to a carbon.
• The suffix is –anoic acid and the carbon attached
to the –OH and double bonded oxygen is counted
in the stem name.
• C2H5COOH is propanoic acid.
• CH2COOH is ethanoic acid. (We are used to seeing
HC2H3O2 as acetic acid, but it is the same as
ethanoic acid.)
• General formula: CnH2n+1COOH
• Class – carboxylic acid
• Functional group – carboxyl
 Functional Group: -C=O
O-R
• Esters are organic compounds where the
alkyl group of the alcohol has replaced the
hydrogen of the carboxylic acid.
• The suffix is –anoate.
• The name puts the alkyl group first followed
by the acid anion.
• E.g. C2H5COOCH3 is methyl propanoate.
• General formula: R-COO-R’
• Class – ester
• Functional group – ester
 Functional Group: -NH2
• Amines have the functional group –NH2.
• The suffix is –anamine.
– Propanamine and butanamine are examples.
– Propanamine can also be named
1-aminopropane
– This is because –NH2 is also substituent group
called amino-.
• Class – amine
• Functional group – amine
Primary, Secondary and Tertiary Amines

• Primary amines have one –NH2 group.

• The H’s can be substituted once or twice
with alkyl groups to form secondary or
tertiary amines.
• A secondary amine is C3H7NHCH3 which is
named N-methylpropanamine.
(The N is used in the name to signify that
methyl is attached to nitrogen.)
• C3H7N(CH3)2 N,N-dimethyl propanamine is a
tertiary amine.
 Functional Group: - C=O
H-N-H
• Amides are derivatives of carboxylic acids where the
–OH is replaced by –NH2.
• The suffix is –anamide and the carbon attached to
the group is part of the stem.
• C2H5CONH2 is propanamide.
• Class – amide
• Functional group – carboxyamide
Primary, Secondary and Tertiary amides

• Primary amides have an –NH2 group.

• Secondary amides have 1 alkyl group bonded to the
nitrogen.
– C2H5CONHCH3 is N-methylpropanamide.
(N-means the alkyl group is bonded to the
nitrogen.)
• Tertiary amides have 2 alkyl groups bonded to the
nitrogen.
– C2H5CON(CH3)2 is N,N-dimethyl propanamide.
• Nitriles have a carbon triple bonded to a nitrogen.
• The suffix is –anenitrile.
• An example C2H5CN is propanenitrile. (Notice the
carbon bonded to the nitrogen is included in the stem
name.)
• Class – nitrile
• Functional group – nitrile
 Functional Group:

• Arenes are known as aromatic compounds and

contain the benzene ring.
• The suffix is –benzene.
• An example would be methyl benzene.
• Class – arene
• Functional group – phenyl
 Benzene

• Benzene has 3 alternating double bonded carbons.

• It has a high degree of unsaturation.

• It has no isomers.
• It does not readily undergo addition reactions
expected of unsaturated compounds.
 Benzene

• The first model for benzene was suggested by

Kekule in 1865 which suggested the cyclic
arrangement of the carbons with alternating double
bonds.
• This model explained some of the known
properties of benzene such as no isomers but it did
not explain the low reactivity.
 Benzene

• Advances in technology provided data to develop

the current model of the benzene structure.

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 Benzene

• Each of the six carbon atoms is sp2 hybridized

forming 3 sigma bonds with angles of 120, making a
planar shape.

• This leaves one unhybridized p electron on each

carbon atom with its dumb-bell shape perpendicular
to the plane of the ring.
 Benzene

• The p orbitals effectively overlap in both

directions spreading themselves out evenly
to be shared by all 6 carbon atoms.
• This forms a delocalized pi electron cloud in
which electron density is concentrated in two
donut-shaped rings above and below the
plane of the ring.
• This very stable arrangement lowers the
internal energy of the molecule.
Benzene

www.en.wikipedia.org
 MORE ON BENZENE

• All carbon bonds are equal and intermediate in length

between single and double bonds.
• The delocalized structure is more stable than the
Kekule structure by about 152kJ/mol.
• Benzene more likely undergoes substitution reactions
rather than addition reactions.
Sample questions
Answers
 Formulae of organic compounds
• Empirical formula: shows the simplest whole
number ratios of different atoms in a compound.
• Molecular formula: shows the actual numbers of
different atoms in a molecule. E.g. C6H12O6
• Structural formula: shows how the atoms are
bonded to each other with the bonds showing
H

H C H

H
• The condensed structural formula shows the order
in which atoms are bonded but some bonds are not
shown. CH3CH2CH2CH2OH or CH3-CH2-CH2-CH2-OH
 Formulae continued
• Skeletal formula: this is a conventional way of
writing the formula of an organic compound in which
carbon and hydrogen atoms are not written. Corners
in the structure represent carbon atoms, and the
number of bonds to the carbon is used to determine
the number of hydrogens bonded to a carbon atom.
 Distinguish between empirical, molecular and
structural formulas

• Structural Butanoic Acid

• Molecular
• Empirical What is the Molecular and empirical
formula?

H H H O Condensed
structural formula

H C C C C OH
H H H CH3(CH2)2COOH
 TRY

• Use the information provided to determine the

empirical and molecular formulae of the compounds
with the following composition:
a). 41.39% carbon, 3.47% hydrogen, and 55.14%
oxygen; molar mass= 116.07g/mol]
b). 54.53% carbon, 9.15% hydrogen, and 36.32%
oxygen; molar mass =88g
c). 64.27% carbon, 7.19% hydrogen, and 28.54%
oxygen; molar mass 168.19g
d. A hydrocarbon containing 17.4% hydrogen by
mass, with a molar mass of 58.1g.
• Answers [1 a) CHO, C4H4O4, b) C2H4O, C4H8O2, c)
C3H4O, C9H12O3 ,d)C2H5, C4H10]
 Empirical formula from combustion
analysis
• This is a method is used the analysis of organic
compounds.
1. The compound is burnt in a stream of pure oxygen.
2. The water vapour produced is passed through a
pre-weighed tube containing anhydrous calcium
chloride which absorbs it.
3. The carbon dioxide left is then passed through a
pre-weighed tube containing potassium hydroxide
which absorbs it.
4. The gain in weights of these two tubes gives the
weights of water and carbon dioxide produced from
burning the organic compounds respectively.
 Combustion chamber

• Below is a typical set for the analysis

 Calculations

• The percentage of carbon and hydrogen are then calculated

from the weights.

12.01x wt CO 2 x100
% of carbon=
44x weight Organic sample

2.01x wt H 2Ox100
% of Hydrogen=
18x weight Organic sample

• The percent of oxygen if present is obtained by subtracting

the sum of the percentages of C and H from 100.
 Example 1
• When 0.232g of a hydrocarbon was burnt in excess oxygen,
0.730g CO2 and 0.298g of water were produced. Deduce the
empirical formula of the hydrocarbon.

12.01x 0.730gx100
% of carbon= = 85.82%
44g/molx 0232g

2.01x 0.298gx100
% of Hydrogen= = 14.28%
18g/molx 0.232g

• Total = 85.82+ 14.28 = 100%

• This means there is no oxygen in the organic compound.

Step 1: Divide the percentage of element by its atomic mass.

85.82 14.28
C= =7.14 H= =14.28
12.01 1

7.14 14.28
C= =1 H= =2
7.14 7.14

The ratio of C to H is 1: 2, given an empirical formula CH2.

 Example 2
• 1. If 1.20g of an organic compound upon combustion produced
1.76g CO2 and 0.76g of water. Calculate
• a) The percentage of each element in the compound.
• b) the empirical formula of the compound.
12.01x1.76gx100
% of carbon= =40.00%
44g/molx1.20g
2.01x 0.76gx100
% of Hydrogen= = 7.02%
18g/mol/molx1.20g

• Total = 40.00 + 7.03 = 47.07%

• This means there is oxygen in the organic compound.
• Percentage oxygen = 100 -47.03 = 52.97%
• You then use these values to deduce the empirical formula.
 Try
1. If. 2.20g of an organic compound of molecular mass
180g/mol upon combustion produced 3.23g CO2 and
1.32g of H2O.
a) Determine the empirical of the compound.
b) Determine the molecular formula.

• 2. A 0.974 grams of quinine (molar mass = 324 g/mol)

is combusted and found to produce 2.642g
CO2, 0.650g H2O and 0.0842 g nitrogen .
a) Determine the empirical of the compound.
b) Determine the molecular formula.
 Hydrocarbons
• Compounds containing only carbon and hydrogen
 Saturated and unsaturated compounds
• A hydrocarbon that contains only carbon-carbon
single bonds is said to be saturated.
• A hydrocarbon that contains one or more carbon-
carbon double bonds, triple bonds, or benzene rings,
is classified as an unsaturated hydrocarbon.
• Alkenes, alkynes, and compounds containing
benzene rings are unsaturated.
• Alkenes and alkynes are aliphatic unsaturated
compounds.
• Benzene and its derivatives are aromatic
unsaturated compounds.
 ALKANES
• Hydrocarbons with only single C-C bonds.
• General formula: CnH2n+2
• The carbons are surrounded by 4 atoms and have a
tetrahedral shape with bond angles of 109.5 degrees.
• The carbon atoms are sp3 hybridized.
• Normal alkanes are formed from strings of carbon
atoms attached to each other.
• Due to the tetrahedral bond angles, they are not
really straight chains, but zigzag shaped.
 BOILING POINT TRENDS

• The boiling point is affected by the length of the

carbon chain.
• Boiling point increases with increasing carbon
number. As the carbon chains get longer, molar
mass increases and melting and boiling points
increase.
• This is caused by the increased number of
temporary dipoles causing stronger van der Waal’s
forces between molecules as their size increases.
Graph showing gradation in B.pt
VOLATILITY IS CAUSED BY FACTORS
• 1. Influence of carbon chain
– The longer the straight chain, the higher the London
dispersion forces so the higher boiling point.
– Branched chain hydrocarbons cannot get in as
close to each other so the London dispersion forces
are not as strong.
– Basically, smaller chains have higher volatility
– branched chains of the same hydrocarbon have
higher volatility.
2. Influence of functional group
• The nature of the functional group may influence
the strength of the intermolecular forces.
• Polar groups have higher boiling points and
those that exhibit hydrogen bonding are higher
still.
• Comparisons are done with similar molar
masses, not similar numbers of carbon atoms.
• Compare ethanol, Mr = 46 and propane Mr = 44.
Ethanol has a boiling pt of 78°C and propane -
42°C. Clearly the hydrogen bonding in ethanol
affects the volatility.
 Trends

• 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.
 NOMENCLATURE

• IUPAC (International Union of Pure and Applied

Chemistry) is an international, non-governmental
organization known for its system of nomenclature
recognized world wide.
• IUPAC uses the size of the molecules and the
functional groups present to logically name
compounds.
 Identify longest chain as the parent

Number of Prefix Name Formula

Carbon
1 Meth- Methane CH4
2 Eth- Ethane C2H6
3 Prop- Propane C3H6
4 But- Butane C4H10
5 Pent- pentane C5H12
6 Hex- hexane C6H14
7 Hep- Heptane C7H16
8 Oct- Octane C8H18
9 Non- Nonane C9H20
10 Dec- Decane C10H22
 IDENTIFY THE SIDE CHAINS OR
SUBSTITUENT GROUPS
• Substituent groups are given as the first part of the
name or are the prefix of the name.
• Common substituents are: methyl-, ethyl-, propyl-,
flouro- (-F), chloro- (-Cl), bromo- (-Br), iodo- (-I), and
amino- (NH2).

• The position of the substituent group is given by a

number followed by a hyphen in front of its name
showing the carbon atom to which it is attached.
 Nomenclature (continued)
• The positions of the substituent groups are specified
by numbering the longest carbon chain of carbon
atoms sequentially starting at the end closest to the
branching.
I CH3
CH3 – CH2 – CH – CH2 – CH2 – CH3
There are 6 carbons in the longest chain so it will be
hexane. Number so that the methyl group attached to
the third carbon from left so the name is 3-
methylhexane.
• Substituents are listed in alphabetical order.
• The prefixes di-, tri-, etc are use to indicate multiple, identical
substituents.
• When 2 or more numbers are used, they are separated by a
comma.
 Example

• The following molecule has 8 carbons with a methyl

group at carbon 4
 Nomenclature

• If there are more than one substituent group of the

same kind, use the prefixes di-, tri-, tetra- before the
name.
• Number to give the carbon with the substituents the
smallest numbers.
• When 2 or more numbers are used, they are
separated by a comma.
 Nomenclature
• Substituents are listed in alphabetical order from the
end that gives the lower number to the substituent
encountered first.
• If there are different substituents in equivalent
positions on opposite ends of the parent chain, give
the substituent of lower alphabetical order the lower
number.

Try: Write the structure of 4-Ethyl-2,2-dimethylhexane

 Cycloalkanes

• Cyclic alkanes are named with the prefix cyclo. E.g.

Cyclohexane
 Try

• Name the following compounds

• a) b)

• c)
Sample questions
Answers
 ISOMERISM IN ALKANES

• Structural isomerism occurs when two molecules

have the same molecular formula but different
arrangements of the atoms.
• The alkanes with the molecular formulas CH4, C2H6,
and C3H8 do not exhibit structural isomerism
All alkanes starting with butane exhibit structural
isomerism.
• Structural isomers exhibit different properties.
 Identifying structural isomerism
• Consider the following molecules

• The molecules are both condensed structural

formulas and line-angle formulas. Each formula has
an unbranched chain of six carbons; the two are
identical and represent the same compound.
 Structural Isomerism

• Consider the following molecules

• Each formula has a chain of five carbons with two

methyl, -CH3, groups.
Although the branches are identical, they are at
different locations on the chains; these formulas
represent structural isomers.
 Naming other organic compounds
• Alkenes have the general formula CnH2n.
• Number to give the carbons with the double bond
the smallest possible numbers.
• Change the ending of the molecule to -ene
• Use the smaller number of the doubly bonded
carbons to indicate the position of the double bond.
The position of the double bond is inserted between
the parent chain and the end of the molecule. E.g.
but-1-ene.
• The position may also be placed at the front of the
molecule. E.g. 1-butene
 Examples
• ewf
 Alkynes

• These are unsaturated compounds with a triple bond

with general molecular formula CnH2n-2.
• Give the triple bond is priority in numbering such
that the carbon with the triple bond is given the
smallest number.
• The ending of the corresponding alkane is change to
–yne
• The position of the triple bond is indicated by the
smaller number of the triply bonded carbon atoms.
• The position of substituents are indicated by the
number of the carbon atoms to which they are
attached.
Examples of alkynes
 Alcohols

• General formula: CnH2n+1OH.

• Number to give carbon with -OH smallest number.
• Locate position of =OH with the number of the
carbon atom to which it is attached.
• Change the ending og the corresponding alkane to
ol.
• Locate other substituents and indicate their
positions by the numbers of the carbon atoms to
which they are attached.
• All other rules pertaining to alkanes apply.
 Examples

• CH3OH methanol
• CH3CH2OH ethanol
• CH3CH2CH2OH propan-1-ol
• CH3CH(OH)CH3 propan-2-ol
• CH3CH2CH2CH2OH butan-1-ol
• CH2ClCH2CH2OH 3-chloropropan-1-ol
 Naming esters
Name the alkyl group derived from the alcohol first
followed by the akanoate group from the acid
Examples
 Ethers

• Ethers contain two akyl groups bonded to an oxygen

atom: R-O-R’ where R and R’ may be the same or
different.

• Ethers do no have intermolecular hydrogen bonding

as the oxygen is not bonded directly to a hydrogen.
Hence ethers have very low melting points and
boiling points. However, they dissolve in water due
to hydrogen bonding between the water molecules
and the oxygen in the ether
 Nomenclature of ethers
• I.U.P.A.C
• Identify the longer chain as parent.
• The carbon bonded to the oxygen in each of the alkyl
groups are number carbon 1 if it is at the end.
• Name the shorter chain as an alkoxy group.
• CH3O- Methoxy
• CH3CH2O- ethoxy
• CH3CH2CH2O- propoxy
• C6H5O- Phenoxy
• Follow the name of alkoxy group with the name of
the longer changer as an alkane.
• Name substituents in alphabetical order of the first
letter in their names.
 Examples

• CH3OCH3 1-methoxymethane
• CH3CH2OCH3 1-methoxyethane
• CH3CH2OCH2CH2CH3
• CH3CHCH3CH2CH2OCH3

• When a double bond is present with the ether group

priority is given to the double bond
 Common names

• Name the two alkyl groups in alphabetical order

followed by ether.
• If the alkyl groups are identical use the prefix di- to
indicate this.
• CH3OCH3 dimethyl ether
• CH3CH2OCH3 ethylmethyl ether
• CH3CH2OCH2CH2CH3 ethyl propyl ether
• CH3CHCH3CH2CH2OCH3
 The carbonyl group
The carbonyl group (>C=O) is the functional
group found in compounds such as aldehydes,
ketones, and carboxylic acids.

⚫ In aldehydes the carbonyl group is at the end of the

carbon chain and so has at least one hydrogen
attached to it.

⚫ In ketones the carbonyl group is in the middle of a

carbon chain and so has two alkyl groups attached
to it.
 Representing aldehydes and
ketones
Aldehydes and ketones are therefore represented either using displayed or
structural formulae.

CH3CHO CH3CH2CH2CHO

CH3COCH2CH3 CH3CH2COCH2CH3
 Naming aldehydes
Aldehydes are named using the suffix –al, and follow the same conventions as for
naming alkanes.

ethanal propanal

2-methylbutanal
 Naming ketones
Ketones are named using the suffix –one.

propanone hexan-3-one

Like alkenes, ketones with four or more carbon atoms display positional
isomerism because the carbonyl group may appear between different carbon
atoms. In these cases, a number is used before the –one to indicate the first
carbon involved.
 Naming ketones
Ketones are named using the suffix –one.

propanone hexan-3-one

Like alkenes, ketones with four or more carbon atoms display positional
isomerism because the carbonyl group may appear between different carbon
atoms. In these cases, a number is used before the –one to indicate the first
carbon involved.
Sample questions
Answers
Benzene. C6H6
Benzene
Reactions of Alkanes, and alkenes
Reactions of Alkanes, and alkenes
Reactions of Alkanes, and alkenes
Reactions of Alkanes, and alkenes
Reactions of Alkanes, and alkenes
Answers
Reactions of Alkanes, and alkenes
Reactions of Alkanes, and alkenes
Reactions of Alkanes, and alkenes
Sample questions
Answers
Reactions of Halogenoalkanes and
Benzene
Oxidation of Alcohols
Oxidation of Alcohols
Oxidation of Alcohols
Esterification
Sample questions
Answers
Reactivity of Halogenoalkanes
Nucleophilic Substitution
Reactivity of benzene
Electrophilic substitution
Sample questions
Answers
Thank you