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ORGANIC CHEMISTRY
8.1 Introduction
the organic compounds are devided into several groups known as homologues series
the homologous series is a series of organic compounds that have similar structural features but differ
from adjacent member by a (-CH2) group
each member of a homologous series has the same chemical properties and can be represented by a
general formula
Homologous Series
General Formula
Example
Functional Group
Alkanes
CnH2n+2
n = 1, 2, 3,.
CH4, n = 1
C C
Alkenes
CnH2n
n = 2, 3, 4,.
C2H4, n = 2
C C
Alkynes
CnH2n-2
n = 2, 3, 4,
C2H2, n = 2
C C
Alcohol
CnH2n+1OH
n = 1, 2, 3,.
CH3OH, n = 1
C OH
Carboxylic acid
CnH2n+1COOH
n = 1, 2, 3,
CH3COOH, n = 1
C COOH
Aldehyde
RCHO
R = alkyl group
CH3CHO, n = 2
Ketone
RCOR
R = alkyl group
CH3COCH3, n = 3
Primary amines
RNH2
R = alkyl group
CH3NH2
R C H
8.2 Hydrocarbons
O
R C R
H
R N
H
CHM167/chapter8/HaslizaYusof
8.3 Alkanes
also called saturated hydrocarbons because they are saturated with hydrogen
the alkanes are named from the Greek numbers according to the number of carbon atom present
the suffix ane is added to the end of each name to indicate that the molecule identified is an alkane
8.3.1 Nomenclature
in this system, the longest continuous chain of carbon atoms called the parent chain- determines the
base name of the compound
the prefixes for the base names depends on the number of carbon atoms in the parent chain
methyl
C2H5
CH2CH3 or
ethyl
fluoro
Cl
chloro
Br
bromo
iodo
CHM167/chapter8/HaslizaYusof
STEP 2
STEP 3
Example:
CH3
CH3
STEP 1
Write the alkane name of the longest continuous chain of carbon atoms. In this
alkane, the longest chain has five carbon atoms, which is pentane
CH3
CH3
STEP 2
CH
pentane
Number the carbon atoms starting from the end nearest a substituent
CH3
CH3
STEP 3
pentane
Give the location and name of each substituent as a prefix to the alkane name.
Place a hyphen between the number and the substituent name
CH3
CH3
1
CH
2
2-methylpentane
3 chloro 2 methylpentane
Use a prefix (di - , tri - , tetra -) to indicate a group that appears more than once. Use commas to separate
two or more numbers
CH3 CH3
CH3
1
2,3 dimethylpentane
When there are two or more substituents, the parent chain is numbered in the direction that gives the
lowest set of numbers
Br
CH3
5
CH3
CH CH2 C CH3
4
Br
CHM167/chapter8/HaslizaYusof
STEP 2
STEP 3
Example:
Write the condensed structural formula for 2,3 dimethylbutane
STEP 1
Draw the main (parent) chain of carbon atoms. For butane, we draw a chain of
four carbon atoms and number it
C C C C
1
STEP 2
Number the chain and place the substituents on the carbons indicated by the
numbers. The first part of the name indicates two methyl groups (CH3-),
one on carbon 2 and one on carbon 3
CH3
C C C C
1
CH3
STEP 3
Add the correct number of hydrogen atoms to give four bonds to each carbon
atom
CH3
CH3 CH CH CH3
1
CH3
2,3 - dimethylbutane
CHM167/chapter8/HaslizaYusof
Exercise
1. Give the IUPAC name for each of the following
a) b)
F
CH3
CH3 C CH3
CH3
c)
d)
CH3 Cl
CH3
CH2
CH CH CH3
Br
CH3
CH2
e) CH3(CH2)5CH3
2. Draw a condensed structural formula for each of the following alkanes
a) 2 methylbutane
b) 3,3 dichloropentane
c) 2,3,5 trimethylhexane
d) 3 iodopentane
e) 2-methylpropane
f) 2-bromo-2,3-dichloropentane
Cl
CH CH2 CH CH3
CHM167/chapter8/HaslizaYusof
8.3.3 Isomers
the structural formulae of methane, ethane & propane can be written only in one way
the hydrocarbon with molecular formula C4H10 has two isomers: butane & 2-methylpropena
H H H H
H C C C C H
CH3
H H H H
CH3 CH CH3
Butane
b)
2 methylpropane
8.3.4 Reactions
Reagent
Bromine, Br2
Effect on alkanes
No effect in the dark. Bromine slowly decolourised in
sunlight. Halogenation reaction
H H
H C C H
Br2
H H
Chlorine, Cl2
uv
light
H Br
H C C H
HBr
HCl
H H
Cl2
uv
light
H Cl
H C C
H H
CHM167/chapter8/HaslizaYusof
8.3.5 Cycloalkanes
Molecular formula has two less H atoms than straight chain, CnH2n
H H
C
H C C H
H
H
cyclopropane
H H
H H
H
C
H C
C H
H
H C C H
H C C H
H H
cyclobutane
H C
C H
C
H
H
H H
cyclohexane
8.4 Alkenes
the suffix ene is added to the end of each name to indicate that the molecule identified is an alkene
CHM167/chapter8/HaslizaYusof
8.4.1 Nomenclature
STEP 3
Example:
CH3
CH3 CH CH CH CH3
STEP 1
Name the longest carbon chain that contains the double bond. There are five
carbon atoms in the longest chain. Replacing the corresponding alkane
ending with ene gives pentene
CH3
pentene
CH3 CH CH CH CH3
STEP 2
Number the longest chain from the end nearest the double bond. The number of
the first carbon in the double bond is used to give the location of the double
bond
CH3
CH3
5
STEP 3
2 pentene
CH CH CH CH3
4
Give the location and name of each substituent (alphabetical order) as a prefix to
the alkene name. The methyl group is located on carbon 4
CH3
CH3
5
CH CH CH CH3
4
4 methyl 2 pentene
Exercise
Give the IUPAC name for each of the following
1.
CH3
CH3
C CH2
2.
CH3
CH3
C C CH3
CH3
CHM167/chapter8/HaslizaYusof
8.4.2 Isomers
b) trans 2- butane
2. 2,3-dichloro-2-butene
a) cis-2,3-dichloro-2-butene
b) trans-2,3-dichloro-2-butene
8.4.3 Reactions
1. halogenation
a) Br2
H H
+
Br2
H C C H
Br Br
1,2 - dibromoethane
Ethene
2. hydrogenation
H H
H C C H
H H
+
H2
H C C H
H H
8.4.4
1. Bromine in CCl4
2. KMnO4 in acid
8.5 Alkyl Halide
H H
H H H H
H C C H
H C C H
H C C C C H
H Cl
H F9
Br H H H
CHM167/chapter8/HaslizaYusof
8.6 Alcohol
H C OH
R C OH
R C OH
primary alcohol, 1
secondary alcohol, 2
tertiary alcohol, 3o
8.6.1 Nomenclature
CH3
Example:
CH3
C CH2 OH
H
STEP 1
Name the longest carbon chain containing the OH group. Replace the e in the
alkane name with ol
CH3
CH3
C CH2 OH
propanol
STEP 2
Number the longest chain starting at the end closest to the OH group
CH3
CH3
3
STEP 3
C CH2 OH
1 - propanol
C CH2 OH
2 methyl 1- propanol
CH3
CH3
CH CH CH3
OH
8.6.2 Reactions
1. Oxidation
H
H C H
H
+
O2
2. Reduction
O
H C H
H C OH
H
+
H2
H C OH
10
H
CHM167/chapter8/HaslizaYusof
3. Halogenation
CH3
CH CH3
OH
2 - propanol
HI
CH3
H2O
I
2 - iodopropane
Hydrogen
iodide
8.7 Aldehyde
CH CH3
general formula: R C H
8.7.1 Nomenclature
STEP 1
Name the longest carbon chain containing the carbonyl group by replacing the e in
the alkane name with al.
No number is needed for the aldehyde group because it always appears at the end
of the chain
STEP 2
Name and number any substituents on the carbon chain by counting the carbonyl
carbon as carbon 1
CH3
CH3 O
CH3
3
CH3
CH C H
2
2 methylpropanal
8.7.2 Reactions
1. Oxidation
H
H C OH
O2
H C H
2. Reduction
O
H C H
H
+
H2
H C OH
H
11
CH CH2 CH2 C H
4
CHM167/chapter8/HaslizaYusof
8.8 Ketone
general formula:
O
R C R
8.8.1 Nomenclature
STEP 1
Name the longest carbon chain containing the carbonyl group by replacing the e in
the alkane with one
STEP 2
Number the parent chain starting from the end, nearest the carbonyl group. Place
the number of the carbonyl carbon in front of the ketone name (propanone and
butanone do not require numbers)
STEP 3
O
CH3
C CH3
CH3
CH3
CH2 C CH3
butanone
propanone
CH2
CH3
1
3 - methylbutanone
CH C CH2 CH3
2
1. Oxidation
OH
O
+
2 bromo 3 - pentanone
8.8.2 Reaction
CH3 CH CH3
Br O
C CH CH3
2
3 - pentanone
O CH3
CH3
C CH2 CH3
O2
CH3
12
C CH3
CHM167/chapter8/HaslizaYusof
general formula:
C OH
O
R C OH
8.9.1 Nomenclature
STEP 1
Name the longest carbon chain containing the carboxyl group and replace the e
of the alkane name by oic acid
STEP 2
Number the carbon chain beginning with the carboxyl carbon as carbon 1
STEP 3
CH3 O
H C OH
CH3
Methanoic acid
8.9.2
CH C OH
2 methylpropanoic acid
Reaction
1. Oxidation
H
CH3 C OH
O
+
O2
CH3
13
C OH
CHM167/chapter8/HaslizaYusof
TUTORIAL 8
1. Draw the structural formula for each of the following organic compounds
a)
b)
c)
d)
e)
f)
g)
h)
i)
j)
k)
2-methylpropane
2-bromo-2,3-dichloropentane
3-methyl-2-hexene
cis-2-butene
2,2,3-trimethylpentane
1-bromo-1-chlorobutane
2-methyl-2-butene
propanal
2,4-heptadiene
2-propanol
2-methyl-2-butanol
2. Draw and name all alkane isomer of the compound with molecular formula of C 5H12
3. Name of the following compound
a) CH3(CH2)5CH3
b) CH3CH(OH)CH2CH3
c) CH3CH2CH2CHO
4. Write the structures of the cis and trans isomers for the 2 butene.
5. Give one test to confirm the presence of the C=C bond in hydrogen.
6. Draw structures containing four carbon atoms for each of the following classes of compound:
a)
b)
c)
d)
e)
Alkane
Alkyl halide
Alcohol
Alkene
Carboxylic acid
7. Write the condensed structures and the IUPAC names for all five possible alcohols with general
formula C5H12O.
8. Identify the functional group of each of the following compounds
a)
CH3CH2COCH2CH2CH3
b)
CH3CH2CH2CHO
c)
CH3CH2COOH
d)
CH3CH2CH CH2
e) CH3CH2CH2OH
14
CHM167/chapter8/HaslizaYusof
f) CH3CH2CH3
9. Predict the product of each of the following reactions
a)
b)
c)
d)
e)
15