Chapter 2

Nomenclature of Organic Compounds

Alkanes
Hydrocarbons are only C and H atoms.

1.Saturated hydrocarbons (Aliphatic)

 Only single bonds with general formula CnH2n+2.

 Aliphatic – “Fat” like.

 can be Straight-chain and branched-chain alkanes

 Can be acyclic (no rings) or cyclic (cycloalkanes).

2. Unsaturated hydrocarbons
Carbon-carbon double bond or triple bonds

The general formula for C=C double bonds is CnH2n.

1
 for triple bonds the general formula is CnH2n-2.
To mention some alkanes

2
Alkanes

3
 Isomerism
 Alkanes may have different isomers
Compounds that have the same molecular formula but different structure are
called constitutional isomers
 Isomers: substances having the same elementary composition and molecular
weight but differing in structure.

Consider C4H10

These structures are constitutional isomers

4
 Isomerism
 Consider C5H12

 These structures are constitutional isomers

5
 Isomerism
 Consider C6H14

 These structures are constitutional isomers 6

 Nomenclature of Alkyl Substituents
 Names and Formulas of Alkyl Groups:

Formula Name Formula Name

CH3- methyl CH3CH2CH2CH2- butyl

CH3CH2- ethyl (CH3)2CHCH2- isobutyl

CH3CH2CH2- propyl CH3CH2CH(CH3)- sec-butyl

(CH3)2CH- isopropyl (CH3)3C- tert-butyl

7
Nonsystematic names; Common names

8
9
 Primary (1o) carbon – a carbon that is bonded to
only one other carbon.
 Secondary (2o) carbon– a carbon that is bonded
to two other carbons.
 Tertiary (3o) carbon– a carbon that is bonded to
three other carbons.

10
Nonsystematic names; Common names

11
Names of Some Alkyl Groups

12
13
 IUPAC Nomenclature of Alkanes
1. Determine the number of carbons in the longest continuous carbon
chain as the parent hydrocarbon.
2. In numbering, the substituent gets the lowest possible number.
• A number and a word are separated by a hyphen
3. Substituent are listed in alphabetical order.
• Numbers are separated by a comma.
• When the same alkyl group branch chain occurs more than
once, indicate this repetition by a prefix (di, tri, tetra, etc.).
• di, tri, tetra, sec, and so on are ignored in alphabetizing.
• iso and cyclo are not ignored in alphabetizing.
4. When both directions lead to the same lowest number for one of
the substituents, the direction that gives the lowest possible
number to one of the remaining substituents is chosen.
14
 Examples
CH3 CH3
7 6 5 3 1
CH3 CH CH2 CH CH CH CH3
4 2
CH3 CH3

2,3,4,6-tetramethylheptane

1 2 3 4
CH3 CH CH CH3 5 4 3 2 1
CH3 CH2 CH2 CH CH3 paren

CH3 CH3 CH3

alkyl group
2,3-dimethylbutane
2-methylpentane

CH3
4 3 2 1 Note: Number the chain so that the
CH3 CH2 C CH3
substituents get the lowest possible
CH3 numbers.
2,2-dimethylbutane 15
 2 1
CH2 CH3 Be careful to choose the parent
chain.
CH3 CH CH2 CH2 CH3
3 4 5 6

3-methylhexane
CH2 CH3
8 7 6 5 4 3 2 1
CH3 CH2 CH2 CH2 C CH CH CH3
CH3 Cl CH3

3-chloro-4-ethyl-2,4-dimethyloctane

Note: Substituents are listed in alphabetical order.

16
 Draw the Compounds
 3-ethylpentane
1 2 3 4 5
CH3 CH2 CH CH2 CH3
CH2 CH3

 2,2,4-trimethylpentane
CH3
1 2 3 4 5
CH3 C CH2 CH2 CH3
CH3 CH3

17
18
19
 IUPAC Nomenclature of Cycloalkanes

1. In the case of a cycloalkane with an attached alkyl

substituent, the ring is the parent hydrocarbon.

2. There is no need to number the position of a single

substituent on a ring.

3. If the ring has two different substituents, they are

cited in alphabetical order and the number 1
position is given to the substituent cited first.

20
 Cycloalkanes
CH2 CH2
=
H2C CH2
H2C CH CH2CH2CH2CH2CH2CH3
Cyclopropane CH2
1-Cyclobutylhexane
CH2
H2C CH2
(CH2)5CH3
or
H2C CH2 =
CH Hexylcyclobutane
CH3 CH3

Methylcyclohexane

CH2 CH2 6
H2C CH CH3 5
1

H2C CH =
4
CH2 CH3 2
3
1-Ethyl-2-methylcyclohexane
21
 IUPAC Nomenclature of Alkyl Halides
 Common name: alkyl group + halogen (fluoride, chloride, bromide, iodide)
 IUPAC name: substituted alkanes, with the substituent prefix for the
halogens end with “O” (fluoro, chloro, bromo, iodo)

22
23
 Classification of Alkyl Halides, Alcohols, and Amines

 The number of alkyl groups attached to the carbon

to which the halogen is bonded determines whether
an alkyl halide is primary, secondary, or tertiary.

24
 The number of alkyl groups attached to the carbon
to which the OH group is attached determines
whether an alcohol is primary, secondary, or tertiary.

25
 The number of alkyl groups attached to the nitrogen
determines whether an amine is primary, secondary, or
tertiary.

26
27
 Conformations of Cyclohexane
• “Chair” conformation

H H
H
H
H H Equatorial
H H hydrogens
H
H
H H 28
 Conformations of Cyclohexane
• “Chair” conformation

H H
H
H
H H Axial
H H hydrogens
H
H
H H 29
30
 Alkenes and alkynes

Hydrocarbons that contain a carbon–carbon double bond are called alkenes.

Alkenes play many important roles in biology. For example
 Ethene is a plant hormone, a compound that controls the plant’s growth
and other changes in its tissues but affects seed germination, flower
maturation, and fruit ripening.
 pheromones: are alkenes released by insects to communicate each other.
Some phermones are used as sex attractants others are used as alarms.
 The general molecular formula for an alkene is also CnH2n
The IUPAC name of an alkene is obtained by replacing the ―ane ending of the
corresponding alkane with ―ene.

31
 IUPAC naming steps of alkenes

1. The longest continuous chain is numbered in the direction of

lowest possible number to the carbon carbon double bond.

2. The name of a substituent is cited before the name of the longest

continuous chain containing the double bond.

3. substituents are cited in alphabetical order

32
4. If the same number for the alkene functional group suffix is
obtained in both directions, the correct name is the name that
contains the lowest substituent number

5. In cyclic alkenes, the double bond is between carbons 1 and 2.

33
 Assignment

Give the IUPAC name for the following compounds

34
 Alkynes are hydrocarbons that contain a carbon–carbon triple bond.
The general formula is CnH2n-2
systematic name of an alkyne is obtained by replacing the ―ane
ending of the alkane name with ―yne.

Assignment :
Give the systematic name for each of the following compounds:

35
 Alcohols
Alcohols :are compounds that contain OH functional group
they are classified as 1o, 2o and 3o.
The systematic name is obtained by replacing the ―e at the end of the
alkane with the suffix ―ol.
for example ethane by ethanol
The IUPAC rules
1.The parent chain should contain the hydroxy functional l group
2.The parent hydrocarbon is numbered in the direction that gives the
hydroxy suffix the lowest possible number.

36
3. If there is a functional group suffix and a substituent, the functional
group suffix gets the lowest possible number.

37
 Ethers

Ethers are compounds in which an oxygen is bonded to two alkyl

substituents. If the alkyl substituents are identical, the ether is a
symmetrical ether. If the substituents are different, the ether is an
unsymmetrical ether.

The common name of an ether consists of the names of the two alkyl
substituents (in alphabetical order)

38
The IUPAC system names an ether as an alkane with an RO substituent.

The RO substituents are named by replacing the ―yl ending in the name
of the alkyl substituent with ―oxy.
For example

39
 Carbonyl Compounds

 The carbonyl group, a carbon double bonded to oxygen, is probably the most
important functional group found in organic compounds.
 Compounds containing carbonyl groups, called carbonyl compounds.
 The acyl group is replaced by the nucleophile as a result called class I

All these are class I

carbonyl cpds which
are derivatives of
carboxylic acids.

40
Class II carbonyl compounds are those in which the acyl group is
attached to a group that cannot be readily replaced by another group.
Aldehydes and ketones belong to this class.

41
Nomenclature of Carboxylic Acids

a carboxylic acid is named by replacing the terminal ―”e” of the

alkane name with ―”oic acid’’.
For example, the one-carbon alkane is methane, so the one-carbon
carboxylic acid is methanoic acid

42
Caron 6 or fewer carboxylic acids named by their common names.
E.g. formic acid (from ants, bees) formica in Latin ant
Acetic acid (vinegar), acetum in Latin vinegar.
Propionic acid from Greek words pro (the first) and pion (―fat).
Butyric acid rancid butter; butyrum in Latin butter
Caproic acid goat’s milk, Caper is the Latin word for ―goat.
In systematic nomenclature, The carbonyl carbon of a carboxylic
acid is always the C-1 carbon.

43
 Acyl halides

1. Acyl halides are compounds that have a halogen atom in place of

the OH group of a carboxylic acid.
2. Acyl halides are named by using the acid name and replacing “ic
acid” with ―”yl chloride” or “yl” bromide”)

44
 Acid Anhydrides
Loss of water from two molecules of a carboxylic acid results in an
acid anhydride. Anhydride means without water.

The anhydride can be symmetrical or mixed based on the two

carboxylic acids forming it.

45
 Esters

• an ester has an OR′ group in place of the OH group of an acid.

• In naming an ester, the name of the group (R′) attached to the
carboxyl oxygen is stated first, followed by the name of the acid, with
―ic acid replaced by ―ate.

Examples

46
 Amides

 An amide has an NH2, NHR, or NR2 group in place of the OH

group of a carboxylic acid.
 named by using the acid name, replacing ―oic acid or ―ic acid
with ―amide.

47
If a substituent is bonded to the nitrogen, the name of the substituent
is stated first alphabetically.

48
 O
Aldehydes
R H

 The name of an aldehyde is obtained by replacing the terminal

―”e” from the name of the parent hydrocarbon with ―”al”.
E.g. a one-carbon aldehyde is methanal; a two-carbon is ethanal.
 The carbonyl carbon is always C1.

49
If the aldehyde group is attached to a ring, the aldehyde is named by
adding “carbaldehyde” to the name of the cyclic compound

50
 O
Ketones
R R
A ketone is named by removing the “e” from the parent alkane and
adding “one”.

The chain is numbered in the direction that gives the carbonyl

carbon the smaller number.

In cyclic ketones, the carbonyl carbon is C1.

51
Summary of Functional Group Nomenclature and priority

52
53
54