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the organic compounds are divided 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
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
RCOR
R = alkyl group
CH3COCH3, n = 3
RNH2
R = alkyl group
CH3NH2
Ketone
Amines
O
R C H
8.2 Hydrocarbons
Functional Group
O
R C R
H
R N
H
CHM 138
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
n
1
2
3
4
5
6
CnH2n+2
CH4
C2H6
C3H8
C4H10
C5H12
C6H14
Parent name
Methane
Ethane
Propane
Butane
Pentane
Hexane
CHM 138
7
8
9
10
C7H16
C8H18
C9H20
C10H22
Heptane
Octane
Nonane
Decane
methyl
C2H5
CH2CH3 or
ethyl
CH3CH2CH2-
propyl
fluoro
Cl
chloro
Br
bromo
iodo
Example:
CH3
CH3
CHM 138
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
STEP 2
STEP 3
Example:
CHM 138
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
Exercise
1. Give the IUPAC name for each of the following
a)
F
b)
CH3
CH3 C CH3
CH3
c)
d)
CH3 Cl
CH3
CH2
Br
CH CH CH3
CH3
CH2
e) CH3(CH2)5CH3
Cl
CH CH2 CH CH3
CHM 138
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-methylpropene
H H H H
H C C C C H
CH3
H H H H
Butane
CH3 CH CH3
2 methylpropane
8.3.4 Cycloalkanes
Molecular formula has two less H atoms than straight chain, CnH2n
H H
C
H C C H
H
H
H H
H C C H
H C C H
H H
cyclopropane
H H
H
C
H C
C H
H
cyclobutane
H C
C H
C
H
H
H H
cyclohexane
CHM 138
8.4 Alkenes
the suffix ene is added to the end of each name to indicate that the molecule identified is an alkene
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
CH CH CH CH3
4
2 pentene
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
CHM 138
Exercise
Give the IUPAC name for each of the following
1.
2.
CH3
CH3
C CH2
CH3
CH3
C C CH3
CH3
8.4.2 Isomers
b) trans 2- butene
2. 2,3-dichloro-2-butene
a) cis-2,3-dichloro-2-butene
b) trans-2,3-dichloro-2-butene
8.5 Alkynes
the suffix yne is added to the end of each name to indicate that the molecule identified is an alkyne
8.5.1 Nomenclature
STEP 3
Example
CHCCH2CH3
1-butyne
CHCCH(Br)CH2CH3
3-bromo-2-pentyne
CHM 138
H H
H H H H
H C C H
H C C H
H C C C C H
H Cl
H F
Br H H H
Aromatic Compounds: Benzene, C6H6, and other unsaturated compounds that resemble it in chemical
behavior.
The aromatic properties of benzene are those that distinguish it from aliphatic hydrocarbons.
8.7.1
Nomenclature
Some common names have been used to frequently that they have been accepted as IUPAC names.
Names of environmentally relevant compounds include the following:
CH3
OH
Benzene
Toluene
Phenol
There are a few methods of naming aromatic compounds.
The ring can be classified as a substituent structure, like a side chain, or as the base structure.
If the ring is named as the side chain it is known as a phenyl group.
If the ring is named as the base structure, it is named as benzene.
Cl
CH3
CH3CHCH2CH2CHCH3
2-methyl-5-phenyl-hexane
as a side chain
chlorobenzene
as the base structure
CHM 138
As the base structure, the location of the substitutions on the benzene ring must be identified.
Instead of numbering the carbons in the benzene ring we label the substitutions as ortho (1,2), meta
(1,3) or para (1,4) to one another.
Cl
1
Cl
Cl
2
Cl
2
3
Cl
ortho-dichlorobenzene
1,2 dichlorobenzene
o-dichlorobenzene
Cl
meta-dichlorobenzene
1,3 dichlorobenzene
m-dichlorobenzene
para-dichlorobenzene
1,4 dichlorobenzene
p-dichlorobenzene
Exercise :
Write the molecular formula and draw the structural formula for each of the following
1. methylbenzene
3. o-dibromobenzene
2. m- dibromobenzene
4. p-dibromobenzene
8.8 Alcohol
H C OH
R C OH
R C OH
primary alcohol, 1o
secondary alcohol, 2o
tertiary alcohol, 3o
8.8.1 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
10
CHM 138
Number the longest chain starting at the end closest to the OH group
STEP 2
CH3
CH3
C CH2 OH
1 - propanol
Name and number other substituents relative to the OH group
STEP 3
CH3
CH3
3
C CH2 OH
2 methyl 1- propanol
CH3
CH3
CH CH CH3
OH
8.9 Aldehyde
general formula: R C H
8.9.1 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
11
CH CH2 CH2 C H
4
CHM 138
8.10 Ketone
general formula:
O
R C R
8.10.1 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
propanone
CH2
CH3
C CH3
CH2
butanone
Br O
CH3
C CH CH3
2
3 - pentanone
O CH3
CH3
C CH2 CH3
CH C CH2 CH3
2
2 bromo 3 - pentanone
3 - methylbutanone
12
CHM 138
general formula:
C OH
O
R C OH
8.11.1 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
Methanoic acid
CH3 O
CH3
CH C OH
2 methylpropanoic acid
13
CHM 138
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
d)
CH3CH2CH CH2
a) CH3CH2CHO
c) CH2CH2CH3
d) CH3CH2CH2COOH
14
CHM 138
e) CH3CH2CH2OCH3
f) CH3(CH2)2CH3
g) CH3CH2CH2CH2OH
9.
17. Classify each of the following alcohols as primary, secondary or tertiary. Give reasons for your
answer.
18. What is the meaning of the term tertiary (3) when it is used to classify alcohols? Draw a structural
formula for the tertiary (3) alcohol of molecular formula C 4H10O?
15