TUTORIAL 1 (INTRODUCTION TO ORGANIC CHEMISTRY)

1.0 Introduction to organic chemistry

a) Give the definition of organic compound.

Compounds which contain carbon atom.

b) Differentiate between organic and inorganic compound.

Property Organic compound Inorganic

compound
Bonding with Usually covalent Often ionic
molecule
Forces between Generally weak Quite strong
molecules (Intermolecular force) (Electrostatic force)
Normal physical Gases, liquids or low- Usually high-
state melting-point solids. melting-point solids.

Flammability Often flammable Usually

nonflammable
Solubility in water Insoluble Soluble
Conductivity Nonconductor Conductor
Rate of chemical Slow and complex Fast and simple
reaction

c) Give the definition of ‘catenation’.

The ability of the elements to form a stable covalent bond between atoms of the
same element, particularly carbon.

1.1 Brief Chemistry of Carbon

Complete the following structure of organic compound by filling hydrogen to the carbon
atoms.

H H H H
a) H C C C C H

H H H H H
b)
H C C C C C H
H H H H
H H
H C C C H
H H H
 H H H
c) H C C C C C H
H H H

H
H C H
H H
d) H C C C C C H
H H
H C H
H

H H H H H
H C C C C C H
e)
H H H
H C H
H

1.2 Classifying of organic compound

Identify the functional groups present in the following compound (make a circle).

a) (alkoxy) b) (carbonyl)

c) (carboxyl) e)

(Carboxylalkonxy)

d) (hydroxyl)
f) (halogen)
1.3 Type of organic compound

Classify each of the following compounds into (aliphatic, alicyclic or aromatic) and
(saturated or unsaturated).

H
H H
a) Aromatic / unsaturated
H H
H

b) Aliphatic / unsaturated

CH2CH3
c) Alicyclic / saturated

d) CH3CH2CH3 Aliphatic / saturated

e) CH2=CHCH3 Aliphatic / unsaturated

Br CH3
 f) Alicyclic / saturated

1.4 Formula of organic compound

Write the structural formulas, condensed formulas, empirical formulas and bond line
formulas (if have) for the following molecules.

a) Butane, C4H10
H H H H CH3CH2CH2CH3
H C C C C H @ C 2H 5
H H H H CH3(CH2)2CH3 E.F B.L.F
S.F C.F
b) Ethanol, C2H6O
H H
H C C OH CH3CH2OH C 2H 6O OH
H H C.F E.F B.L.F
S.F
c) Propene, C3H6
H H H
H C C C H CH3CH CH2 CH2
H C.F E.F B.L.F
S.F

d) 2-pentyne, C5H8
H H H
H C C C C C H CH3CH2C CCH3 C 5H 8
H H H C.F E.F B.L.F
S.F
e) Hexane, C6H14
H H H H H H CH3CH2CH2CH2CH2CH3
H C C C C C C H @ C 3H 7
H H H H H H CH3(CH2)4CH3
E.F B.L.F
S.F C.F

1.5 Isomers

a) State 2 types of isomers and define each type.

i. Structural isomer
 Compound with the same number of atoms and bonds (molecular
formula) but with different arrangement.

ii. Stereoisomer
Compound with the same molecular formula and structural formula but
with different arrangement of their bond in space.

b) Draw the structural formulas for all the structural isomers of the following
compound and give their respective IUPAC name.

i. C4H10 (hint : has 2 isomers)

H2 H
CH3 C C CH3 CH3 C CH3
H2
CH3
butane 2-methylpropane
ii. C5H12 (hint : has 3 isomers)
CH3 CH3
H2 H2 CH3 C CH3
CH3 C C C CH3 CH3 C H
C CH3
H2 2
CH3
pentane 2-methylbutane 2,2-dimethylpropane
iii. C6H14 (hint : has 5 isomers)
CH3
H2 H2 H2 H2 CH3 H H
2 2 H 2 H2
CH3 C C C C CH3 CH3 C C C CH3 CH3 C C C CH3

hexane 2-methylpentane 3-methylpentane

CH3
H2 H H
CH3 C C CH3 CH3 C C CH3
CH3 CH3 CH3
2,2-dimethylbutane 2,3-dimethylbutane

c) From the following pairs of molecules, identify which are cis and trans isomers.

CH3 H CH3 CH3

i. C C C C
H CH3 H H
Trans cis

CH3 I CH3 H
ii. C C C C
Br H Br I
Cis trans

1.6 Naming of Organic Compounds According to IUPAC System

Identify the longest carbon chain for the following organic compounds and give their
respective IUPAC name.
 6
CH3 CH3
H2
a) H 2C
5 4 3
C C CH3 CH3
1 2 3 4
2
CH2 d) CH3 C CH2 CH3
H
1
CH3 Four (2-methylbutane)
Six (3,3-dimethylhexane)
CH3
H H H
1 2 3 4 5 2 6 2 7 2 8
1 2 3 4 5
e) CH3 C CH CH C C C CH3
b) CH3─CH2─CH2─CH2─CH3 H2
Five (pentane) H2C CH3
Eight (4-ethyl-3-methyloctane)
H 3C CH3
H H2
1 2 3 2 4
CH3 C C CH C CH3 f) 1CH 2
C
3
CH3
c) H 3
5
H 2C
CH3
6
CH2 Three (2,2-dimethylpropane)
7
CH3
Seven (4-ethyl-2-methylheptane)