CAPE Chemistry – UNIT 2 – Chemical Principles and Applications II

Module 1 – The Chemistry of Carbon Compounds. Lecture Notes 1

Structure and Formula

The Carbon Atom

Organic Chemistry is the Chemistry of Carbon compounds. Carbon compounds are far more numerous than
those of any other elements because carbon atoms are able to bond together to form a wide range of rings and
chains (up to 5000 in length), that is it has the ability to catenate. Catentation is the tendency of identical
atoms to form covalent bonds with each other and hence form chains.

The Chemistry of the Carbon Atom

The carbon atom has four (4) valence electrons and can form four covalent bonds with other atoms. Hence the
carbon atom is said to be tetravalent or exhibits tetravalency. In order for carbon to form four bonds, there
must be four unpaired electrons. Consider the electrons-in-boxes configuration of the carbon atom.

In order to there to be four unpaired electrons in the carbon atom, hybridization must occur. Hybridization is
the mixing/overlapping of atomic orbitals to form new orbitals of identical energy. Developed by Linus
Pauling, the concept of hybrid orbitals was a theory created to explain the structures of molecules in space.
The theory consists of combining atomic orbitals (ex: s,p,d,f) into new hybrid orbitals (ex: sp, sp2, sp3).The
following are the shapes of the hybridized orbitals.

Figure 1: sp3 hybridized orbitals

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 Figure 2: sp2 hybridized orbitals

Figure 3: sp hybridized orbitals

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Determine the hybridization on the carbon with the asterisk in the following organic compounds.

1. 2.

3. 4.

5. 6.

Kinetic and Molecular Stability

Another reason why carbon forms so many compounds is that its compounds are kinetically very stable. The
activation energy required to break a carbon-carbon single bond is high. Once the activation energy is
overcome at high temperatures, carbon compounds combusts readily in the presence of air. These reactions
are highly exothermic because carbon compounds are thermodynamically unstable. It is this combination of
high activation energy and exothermic combustion that makes organic compounds very useful as fuels.

Factors affecting the physical and chemical properties of organic compounds

The physical and chemical properties of organic compounds, depends on two (2) factors:

1. The number and arrangement of carbon atoms in the molecule.

A number of important physical properties are determined by the number of carbon atoms in the
molecule. The greater the number of carbon atoms, the larger the Van der Waal’s forces and the higher
the melting points, boiling points and viscosity. In many cases, all the carbon atoms are arranged in a
straight chain. Such compounds are referred to as aliphatic carbon compounds. Often, however, there
are shorter chains of carbon atoms branching off a longer chain. These are known as branched
molecules. Carbon atoms can also be arranged to form rings. These are known as aromatic carbon
compounds or cyclic molecules. The most common number of carbon atoms in a ring is 6.

2. The functional groups in the molecule.

Functional groups are specific atoms or groups of atoms other than carbon and hydrogen, attached to
a main chain that gives rise to a particular chemical property in the compound. Carbon-carbon double
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 bonds are also functional groups. Organic molecules are classified according to the dominant
functional groups on the molecule.

Table 1: Showing the Homologous series and their functional groups

General Formula Functional Group Prefix/Suffix Example

Homologous
Series
CnH2n+1COOH -carboxylic acid Ethanoic acid
Carboxylic acid
-oic acid

CnH2n+1COOCxH2x+1 -oate Methyl

Ester
ethanoate

CnH2n+1COCl -oyl chloride Ethanoyl

Acyl/acid
chloride
chloride

CnH2n+1N(CxH2x+1)2 -amide Ethanamide

Amide
-carboxamide

CnH2n+1CN
Nitrile -nitrile Ethanonitrile

-cyano
CnH2n+1CHO
Aldehyde -al Ethanal

-carbaldehyde
CnH2n+1COCxH2x+1
Ketone -one Propan-2-one

CnH2n+1OH
Alcohol -ol Ethanol

CnH2n+1NH2
Amine -amine Ethanamine

Amino-

CnH2n
Alkene -ene Ethene

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 CnH2n-2
Alkyne -yne Ethyne

CnH2n+2 -
Alkane -ane Ethane
CnH2n+1OCxH2x+1
Ether -ane Methoxy
methane
Alkoxy-
CnH2n+1X
Alkyl halide/ Halo- Bromomethane
Halogenoalkane Where X= F, Cl, Br -ane
or I
CnH2n+1NO2
Nitro Nitro- Nitromethane

-ane

Note:
 R- Represents an alkyl group, that is, a carbon chain.
 A homologous series is a family or group of compounds with similar chemical properties and
differ from each other by the addition of –CH2 groups. Compounds of the same homologous series
have similar chemical properties because they have similar bonding. They also have the same
general formula and exhibits similar trends in physical properties.

Representing Organic Compounds

1. Empirical Formula – The simplest whole number ratio of the atoms of the elements in a compound.
2. Molecular Formula – the actual number of each element in the compound. It is a multiple of the
empirical formula.
3. Structural Formula – Shows the actual arrangement of each atom in the molecule of a compound.
There are two forms of structural formula
- Displayed Structural Formula – all bonds are clearly shown.

- Condensed Structural Formula – bonds not shown.

4. Stereo-chemical Formula – represents the bond angles of each atom present in a molecule and
attempts to represent the shape of that molecule.

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Empirical and Molecular Formula from Experimental Data

Question 1: Calculate the empirical formula of a compound of carbon, hydrogen and iodine that contains
8.45% carbon, 2.11% hydrogen and 89.44% iodine by mass. [RAM: C=12, H=1, I=127]

Question 2: Propene contains carbon and hydrogen only. When 25cm3 of propane reacts with exactly 125 cm3
oxygen, 75 cm3 of CO2 is formed. Deduce the molecular formula of propane and write a balanced
chemical equation for the reaction.

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Question 3: A 1.50g sample of hydrocarbon, undergoes complete combustion to produce 4.4g of CO2 and
2.70g of H2O. What is the empirical formula of this compound?

Practice Questions:
1. 6g of a hydrocarbon contains 4.8g of carbon and 1.2g of hydrogen. The relative molecular mass of the
hydrocarbon is 30. Determine the empirical and molecular formula of this hydrocarbon.
2. Aniline, a starting material for urethane plastic foams consists of C, H and N. Combustion of such
compounds yields CO2, H2O and N2 as products. If the combustion of 9.71g of aniline yields 6.63g
H2O and 1.46g N2, what is its empirical formula? The molar mass of aniline is 93g/mol. What is its
molecular formula?
3. The percentage composition of acetic acid is found to be 39.9% C, 6.7% H, and 53.4% O. Determine
the empirical formula of acetic acid. The molar mass was determined by experiment to be 60.0 g/mol.
What is the molecular formula?
4. Adipic acid is used in the commercial manufacture of Nylon. The composition of the acid is 49.3% C,
6.9% H, and 43.8% O by mass. The molecular weight is 146. What is the molecular formula for Adipic
Acid?
5. Caffeine, a stimulant found in coffee, tea, and chocolate, contains 49.48% carbon, 5.15% hydrogen,
28.87% nitrogen, and 16.49% oxygen by mass and has a molar mass of 194.2 g/mol. Determine the
molecular formula of caffeine.
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 6. Give the molecular formula of the compounds illustrated below.

7. Many homes in rural America are heated by propane gas, a compound that contains only carbon and
hydrogen. Complete combustion of a sample of propane produced 2.641 g of carbon dioxide and 1.442
g of water as the only products. Find the empirical formula of propane.
8. Cumene is a compound containing only carbon and hydrogen that is used in the production of acetone
and phenol in the chemical industry. Combustion of 47.6 mg cumene produces some CO2 and 42.8 mg
water. The molar mass of cumene is between 115 and 125 g/mol. Determine the empirical and
molecular formulas.
9. A compound contains only C, H, and N. Combustion of 35.0 mg of the compound produces 33.5 mg
CO2 and 41.1 mg H2O. What is the empirical formula of the compound?
10. A compound contains only carbon, hydrogen, and oxygen. Combustion of 10.68 mg of the compound
yields 16.01 mg CO2 and 4.37 mg H2O. The molar mass of the compound is 176.1 g/mol. What are
the empirical and molecular formulas of the compound?

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