IB Chemistry on Homologous series, Functional gp and nomenclature

1. http://lawrencekok.blogspot.com
Prepared by
Lawrence Kok
Tutorial on Homologous Series , Functional Groups and Nomenclature

2. Class Functional group/name Suffix Examples Formula
alkane C - C ane ethane CnH2n+2
alkene C = C Alkenyl ene ethene CnH2n
alkyne C ≡ C Alkynyl yne ethyne CnH2n-2
alcohol O-H Hydroxyl ol ethanol CnH2n+1OH
ether C – O - C Ether oxyalkane methoxymethane R –O -R
ketone O
‖
C – C - C
Carbonyl one propanone CnH2nO
or
R-CO-R
aldehyde C = O
‫׀‬
H
Aldehyde anal ethanal CnH2nO
or
R -CHO
Carboxylic
acid
O
‖
C – O H
Carboxyl oic acid ethanoic acid CnH2n+1COOH
ester O
‖
C – O –C
Ester oate ethyl ethanoate R – COO-R
amide CONH2 Amide anamide propanamide
amine NH2 Amine amine ethanamine
nitrile C ≡ N Nitrile nitrile propanenitrile
halogenoalkane F, Br, CI, I Halogeno chloroethane R - CI
Functional group
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – O-H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Hydrocarbon skeleton Functional gp
IUPAC nomenclature
Systematic naming organic molecules
H CI O
‫׀‬ ‫׀‬ ‖
H - C – C – C - OH
‫׀‬ ‫׀‬
H H C1 – functional gp
C2 – substituent gp - CI
2 – chloropropanoic acid
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
Organic software for 3D model Click here resources Rasmol
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3 2 1

3. H CH3 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – O-H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Hydrocarbon skeleton Functional gp
Hydrocarbon
Aliphatic Aromatic
Saturated Unsaturated
benzene alkylbenzene
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
Alkane Cycloalkane
Compound Ethane Ethanoic acid
Empirical formula CH3 CH2O
Molecular formula C2H6 C2H4O2
Full SF
Condensed SF CH3CH3 CH3COOH
Stereochemical
formula
(3D)
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H H
H O
‫׀‬ ‖
H - C - C - OH
‫׀‬
H
Organic Chemistry
Cycloalkene Alkene
IUPAC nomenclature
Ring form
Functional group
Structural formula
2 – chloropropanoic acid
no aromatic ring
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
H CI O
‫׀‬ ‫׀‬ ‖
H - C – C – C - OH
‫׀‬ ‫׀‬
H H C1 – functional gp
C2 – substituent gp - CI
CH3(CH2)3CH3
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
Use of parenthesis
Repeat CH2 x 3
CH3CH(CH3)(CH2)2CH3
Repeat CH2 x 2CH3 branch
H CH3 H CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
CH3CH(CH3)CH2CH(CH3)CH3
CH3 branch
3 2 1
benzene ring
inside

4. H CH3 H CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H CH3 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
CI Br H
H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
IUPAC nomenclature
2 – chloropropanoic acid
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
H CI O
‫׀‬ ‫׀‬ ‖
H - C – C – C - OH
‫׀‬ ‫׀‬
H H C1 – functional gp
C2 – substituent gp - CI
CH3(CH2)3CH3
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
Use of parenthesis
Repeat CH2 x 3
CH3CH(CH3)(CH2)2CH3
Repeat CH2 x 2CH3 branch
CH3CH(CH3)CH2CH(CH3)CH3
CH3 branch
Number
carbon
Alkyl
gp
Structure formula
1 Methyl CH3 -
2 Ethyl CH3CH2 -
3 Propyl CH3CH2CH2 -
4 Butyl CH3(CH2)2CH2 -
5 Pentyl CH3(CH2)3CH2 -
6 Hexyl CH3(CH2)4CH2 -
7 Heptyl CH3(CH2)5CH2 -
8 Octyl CH3(CH2)6CH2 -
R Alkyl R -
Substituents - Gp attach to main carbon chain
R - Alkyl gp (carbon branches)
H C2H5 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
2 -methylbutane
2 - ethylpentane
2, 3- dimethylbutane
1 2
2 3 4 51
1 2 3 4
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
CI CI H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
CI CH3 H
1
1
2
2 3
1 2 3
1 - chloro-2-bromopropane
1, 2 - dichloropropane
1-chloro-2-methylpropane
C2H5
‫׀‬
C2H5 - C – H
‫׀‬
C2H5
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H OH H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C = C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
4 3 2 1
but – 1- ene
butan – 2- ol
1 2 3 4
3 - ethylpentane
3
Start with smallest number
Start with smallest number
Number from end of chain giving substituent lowest possible number
3 2 1
substituents – attached to main carbon chain

5. C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3 CH3
‫׀‬
CH3
Nomenclature for Organic Molecules
Name the parent (longest unbranched carbon chain)
Choose chain which has more alkyl groups attached
1
C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3 CH3
‫׀‬
CH3
7 carbon - heptane
C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3 CH3
‫׀‬
CH3
7 carbon - heptane
2
C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3 CH3
‫׀‬
CH3
4 alkyl gps
Number from end giving substituent lowest possible number3
C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3 CH3
‫׀‬
CH3
1 2 3 4 5 6 7
2 or more identical substituent present
2 - di , 3- tri , 4 - tetra .
2, 4, 5 trimethyl
3 - ethyl
4
Use comma, to separate numbers
Use hyphen – to separate number and word
Write prefix and parent as one word
Arrange substituents according alphabetical order
C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3 CH3
‫׀‬
CH3
1 2 3 4 5 6 7
3 -ethyl-2, 4, 5-trimethylheptane
Choose chain which has more alkyl groups attached
3 alkyl gps
C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3 CH3
‫׀‬
CH3
7 6 5 4 3 2 1
3, 4, 6 trimethyl
5 - ethyl
2, 4, 5 -trimethyl-3-ethylheptane
Name the parent (longest unbranched carbon chain)
wrong
wrong
wrong
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6. • member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n+2
• end with ane
Class Functional gp Suffix Example Formula
Alkane C - C - ane ethane CnH2n+2
Homologous Series
Class Functional Suffix Example Formula
Alkene Alkenyl - ene ethene CnH2n
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H H
• member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n
• end with ene
H
‫׀‬
H - C – H
‫׀‬
H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Number
carbon
Word IUPAC
name
Structure formula Molecular
formula
1 Meth Methane CH4 CH4
2 Eth Ethane CH3CH3 C2H6
3 Prop Propane CH3CH2CH3 C3H8
4 But Butane CH3(CH2)2CH3 C4H10
5 Pent Pentane CH3(CH2)3CH3 C5H12
6 Hex Hexane CH3(CH2)4CH3 C6H14
7 Hept Heptane CH3(CH2)5CH3 C7H16
8 Oct Octane CH3(CH2)6CH3 C8H18
9 Non Nonane CH3(CH2)7CH3 C9H20
10 Dec Decane CH3(CH2)8CH3 C10H22
methane ethane propane butane
Saturated hydrocarbon (C – C single bond)
Number
carbon
IUPAC
name
Structure formula Molecular
formula
2 Ethene CH2CH2 C2H4
3 Propene CH2=CHCH3 C3H6
4 Butene CH2=CHCH2CH3 C4H8
5 Pentene CH2=CH(CH2)2CH3 C5H10
6 Hexene CH2=CH(CH2)3CH3 C6H12
7 Heptene CH2=CH(CH2)4CH3 C7H14
8 Octene CH2=CH(CH2)5CH3 C8H16
9 Nonene CH2=CH(CH2)6CH3 C9H18
10 Decene CH2=CH(CH2)7CH3 C10H20
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
C = C – C - H
‫׀‬ ‫׀‬
H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
C = C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
Unsaturated hydrocarbon (C = C double bond)
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
C = C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
ethene propene butene pentene

7. Class Functional group/name Examples
alkene C = C Alkenyl ethene
alkyne C ≡ C Alkynyl ethyne
alcohol OH Hydroxyl ethanol
ether C – O - C Ether methoxymethane
ketone O
‖
C – C - C
Carbonyl propanone
aldehyde CHO Aldehyde ethanal
Carboxylic
acid
COOH Carboxyl ethanoic acid
ester O
‖
C – O -R
Ester ethyl ethanoate
amide O
‖
C – NH2
Amide propanamide
amine NH2 Amine ethanamine
nitrile C ≡ N Nitrile propanenitrile
Class Functional gp Suffix Example Formula
Alkane C - C - ane ethane CnH2n+2
Homologous Series
carbon IUPAC
name
Structure formula Molecular
formula
Boiling
point
1 Methane CH4 CH4 Gas
2 Ethane CH3CH3 C2H6 Gas
3 Propane CH3CH2CH3 C3H8 Gas
4 Butane CH3(CH2)2CH3 C4H10 Gas
5 Pentane CH3(CH2)3CH3 C5H12 Liquid
6 Hexane CH3(CH2)4CH3 C6H14 Liquid
Physical properties
• Increase RMM / molecular size
•RMM increase ↑ - Van Der Waals forces stronger ↑
↓
Melting /boiling point increases ↑
(Increasing polarisability ↑)
London dispersion forces/temporary dipole ↑
1 2 3 4 5 6 7 8 9 10
number carbons – RMM ↑
150
100
50
0
-50
-100
-150
-200
m/p+ b/p
increase ↑
boiling point
room temp
gas
liquid
Homologous Series
number
Carbons / RMM ↑1 2 3 4 5 6 7 8 9 10
boiling point
boiling point increase with increase carbon atoms
alcohol
alkane
alkene
alkyne
London dispersion force
(temporary dipole)
H2 bonding
carboxylic acid > alkane/alkene/alkyne
alcohol
carboxylic acid

8. • member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n+2
• end with ane
Class Functional gp Suffix Example Formula
Alkane C - C - ane ethane CnH2n+2
Homologous Series
Class Functional Suffix Example Formula
Alkene C = C - ene ethene CnH2n
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H H
• member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n
• end with ene
H
‫׀‬
H - C – H
‫׀‬
H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Number
carbon
Word IUPAC name Structure formula Molecular
formula
1 Meth Methane CH4 CH4
2 Eth Ethane CH3CH3 C2H6
3 Prop Propane CH3CH2CH3 C3H8
4 But Butane CH3(CH2)2CH3 C4H10
5 Pent Pentane CH3(CH2)3CH3 C5H12
methane ethane propane butane
Saturated hydrocarbon
Number
carbon
IUPAC name Structure formula Molecular
formula
2 Ethene CH2=CH2 C2H4
3 Propene CH2=CHCH3 C3H6
4 Butene CH2=CHCH2CH3 C4H8
5 Pentene CH2=CH(CH2)2CH3 C5H10
6 Hexene CH2=CH(CH2)3CH3 C6H12
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
C = C – C - H
‫׀‬ ‫׀‬
H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
C = C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
Unsaturated hydrocarbon
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
C = C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
ethene propene butene pentene
Structural formula – arrangement atoms in molecule (2/3D) Structural formula – arrangement atoms in molecule (2/3D)
Display full SF Condensed SF Ball /stick model Spacefilling
ethane
CH3CH3
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H H
propene
Display full SF Condensed SF Ball /stick model Spacefilling
H H H
‫׀‬ ‫׀‬ ‫׀‬
C = C – C - H
‫׀‬ ‫׀‬
H H
CH2=CHCH3

9. • member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n-2
• end with yne
Class Functional gp Suffix Example Formula
Alkyne C ≡ C - yne ethyne CnH2n-2
Homologous Series
Class Functional Suffix Example Formula
Alcohol Hydroxyl - ol methanol CnH2n+1OH
H - C ≡ C – H
• member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n+1OH
• end with ol
H
‫׀‬
H - C ≡ C – C – H
‫׀‬
H
Number
carbon
IUPAC name Structure formula Molecular
formula
2 Ethyne CH≡CH C2H2
3 Propyne H-C≡C-CH3 C3H4
4 Butyne H-C≡C-CH2CH3 C4H6
5 Pentyne H-C≡C-(CH2)2CH3 C5H8
6 Hexyne H-C≡C-(CH2)3CH3 C6H10
ethyne propyne butyne
Number
carbon
IUPAC
name
Structure formula Molecular
formula
1 Methanol CH3OH CH3OH
2 Ethanol CH3CH2OH C2H5OH
3 Propanol CH3CH2CH2OH C3H7OH
4 Butanol CH3(CH2)2CH2OH C4H9OH
5 Pentanol CH3(CH2)3CH2OH C5H11OH
methanol ethanol propanol butanol
H H
‫׀‬ ‫׀‬
H - C ≡ C – C – C- H
‫׀‬ ‫׀‬
H H
H
‫׀‬
H - C – OH
‫׀‬
H
H H
‫׀‬ ‫׀‬
H - C – C – OH
‫׀‬ ‫׀‬
H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬
H H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Functional gp Hydrocarbon skeleton Hydrocarbon skeleton Functional gp
Structural formula – arrangement atoms in molecule (2D)
Ball /stick model SpacefillingCondensed SFDisplay full SF
H
‫׀‬
H - C ≡ C – C – H
‫׀‬
H
CH≡C-CH3
propyne
Structural formula – arrangement atoms in molecule (2D)
Display full SF Condensed SF Ball /stick model Spacefilling
H H
‫׀‬ ‫׀‬
H - C – C – OH
‫׀‬ ‫׀‬
H H
CH3CH2OH
ethanol

10. • member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2nO
• end with one
Class Functional gp Suffix Example Formula
Ketone Carbonyl (C=O) - one propanone CnH2nO
Homologous Series
Class Fumctional Suffix Example Formula
Aldeyde Aldeyde - al methanal CnH2nO
• member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2nO
• end with al
Number
carbon
IUPAC name Structure formula Molecular
formula
3 Propanone CH3COCH3 C3H6O
4 Butanone CH3COCH2CH3 C4H8O
5 Pentanone CH3CH2COCH2CH3 C5H10O
6 Hexanone CH3CH2COCH2CH2CH3 C6H12O
7 Heptanone CH3CH2COCH2CH2CH2CH3 C7H14O
propanone butanone pentanone
Number
carbon
IUPAC
name
Structure formula Molecular
formula
1 Methanal HCHO CH2O
2 Ethanal CH3CHO C2H4O
3 Propanal CH3CH2CHO C3H6O
4 Butanal CH3(CH2)2CHO C4H8O
5 Pentanal CH3(CH2)3CHO C5H10O
methanal ethanal propanal butanal
H - C = O
‫׀‬
H
H
‫׀‬
H - C – C = O
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – C = O
‫׀‬ ‫׀‬ ‫׀‬
H H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C = O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H O H
‫׀‬ ‖ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬
H H
H O H H
‫׀‬ ‖ ‫׀‬ ‫׀‬
H - C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
H O H H H
‫׀‬ ‖ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Functional gp Hydrocarbon skeleton Hydrocarbon skeleton Functional gp
Structural formula – arrangement atoms in molecule (2D) Structural formula – arrangement atoms in molecule (2D)
Display full SF Condensed SF Ball /stick model Spacefilling Display full SF Condensed SF Ball /stick model Spacefilling
H O H
‫׀‬ ‖ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬
H H
CH3COCH3
propanone ethanal
H
‫׀‬
H - C – C = O
‫׀‬ ‫׀‬
H H
CH3CHO

11. • member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n+1COOH
• end with oic acid
Class Functional Suffix Example Formula
Carboxylic acid Carboxyl - oic acid ethanoic acid CnH2n+1COOH
Homologous Series
Class Functional Suffix Formula
Ester Ester - oate R –COO-R
• member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2nO2
• end with oate
methanoic acid ethanoic acid propanoic acid
Number
carbon
IUPAC name Structure formula Molecular
formula
1 Methyl methanoate HCOOCH3 R–COO-R
2 Methyl ethanoate CH3COOCH3 R–COO-R
3 Methyl propanoate CH3CH2COOCH3 R–COO-R
4 Methyl butanoate CH3CH2CH2COOCH3 R–COO-R
methyl methanoate methyl ethanoate methyl propanoate
Number
carbon
IUPAC name Structure formula Molecular
formula
1 Methanoic acid HCOOH HCOOH
2 Ethanoic acid CH3COOH CH3COOH
3 Propanoic acid CH3CH2COOH C2H5COOH
4 Butanoic acid CH3(CH2)2COOH C3H7COOH
5 Pentanoic acid CH3(CH2)3COOH C4H9COOH
O
‖
H - C - O H
H O
‫׀‬ ‖
H - C - C - OH
‫׀‬
H
H H O
‫׀‬ ‫׀‬ ‖
H - C – C – C - OH
‫׀‬ ‫׀‬
H H
O H
‖ ‫׀‬
H - C – O – C - H
‫׀‬
H
H O H
‫׀‬ ‖ ‫׀‬
H - C - C – O - C - H
‫׀‬ ‫׀‬
H H
H H O H
‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C – C – C – O - C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
Structural formula – arrangement atoms in molecule (2D)
Hydrocarbon skeleton Functional gp
Display full SF Condensed SF Ball /stick model Spacefilling
O
‖
H - C - O H
methanoic acid
HCOOH
Hydrocarbon skeleton Functional gp
Structural formula – arrangement atoms in molecule (2D)
Display full SF Condensed SF Ball /stick model Spacefilling
O H
‖ ‫׀‬
H - C – O – C - H
‫׀‬
H
HCOOCH3
Methyl methanoate

12. • member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n+1NH2
• end with amine
Class Functional Suffix Example Formula
Amine NH2 - amine ethanamine CnH2n+1NH2
Homologous Series
Class Functional Suffix Example Formula
Amide Amide - amide ethanamide CnH2n+1CONH2
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – N - H
‫׀‬ ‫׀‬
H H
• member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n+1CONH2
• end with amide
H H
‫׀‬ ‫׀‬
H - C – N - H
‫׀‬
H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – N - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
Number
carbon
IUPAC name Structure formula Molecular
formula
1 Methanamine CH3NH2 CH3NH2
2 Ethanamine CH3CH2NH2 C2H5NH2
3 Propanamine CH3CH2CH2NH2 C3H7NH2
4 Butanamine CH3(CH2)2CH2NH2 C4H9NH2
5 Pentanamine CH3(CH2)3CH3NH2 C5H11NH2
methanamine ethanamine propanamine
Number
carbon
IUPAC name Structure formula Molecular formula
1 Methanamide HCONH2 HCONH2
2 Ethanamide CH3CONH2 CH3CONH2
3 Propanamide CH3CH2CONH2 C3H7CONH2
4 Butanamide CH3(CH2)2CONH2 C4H9CONH2
5 Pentanamide CH3(CH2)3CONH2 C5H11CONH2
O H
‖ ‫׀‬
H - C – N - H
H O H
‫׀‬ ‖ ‫׀‬
H - C – C – N - H
‫׀‬
H
H H O H
‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C – C – C – N - H
‫׀‬ ‫׀‬
H H
methanamide ethanamide propanamide
Structural formula – arrangement atoms in molecule (2D)
Hydrocarbon skeleton Functional gp
Display full SF Condensed SF Ball /stick model Spacefilling
methanamine
H H
‫׀‬ ‫׀‬
H - C – N - H
‫׀‬
H
CH3NH2
Hydrocarbon skeleton Functional gp
Structural formula – arrangement atoms in molecule (2D)
Display full SF Condensed SF Ball /stick model Spacefilling
methanamide
O H
‖ ‫׀‬
H - C – N - H HCONH2

13. • member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n+1CN
• end with nitrile
Class Functional Suffix Example Formula
Nitrile C ≡ N - nitrile ethanenitrile CnH2n+1CN
Homologous Series
Class Functional Suffix Example
Ether Ether -oxyalkane methoxymethane
H
‫׀‬
H - C – C ≡ N
‫׀‬
H
• member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula R – O - R
• end with oxyalkane
H - C ≡ N
H H
‫׀‬ ‫׀‬
H - C – C – C ≡ N
‫׀‬ ‫׀‬
H H
Number
carbon
IUPAC name Structure formula Molecular
formula
1 Methanenitrile HCN HCN
2 Ethanenitrile CH3CN CH3CN
3 Propanenitrile CH3CH2CN C2H5CN
4 Butanenitrile CH3(CH2)2CN C3H7CN
5 Pentanenitrile CH3(CH2)3CN C4H9CN
methanenitrile ethanenitrile propanenitrile butanenitrile
Number
carbon
IUPAC name Structure formula Molecular
formula
1 Methoxymethane CH3 - O – CH3 R –O -R
2 Methoxyethane CH3CH2 - O – CH3 R –O -R
3 Methoxypropane CH3CH2CH2 - O –CH3 R –O -R
4 Methoxybutane CH3(CH2 )3 - O –CH3 R –O -R
5 Methoxypentane CH3(CH2 )4 - O –CH3 R –O -R
methoxymethane methoxyethane methoxypropane
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C ≡ N
‫׀‬ ‫׀‬ ‫׀‬
H H H
H H
‫׀‬ ‫׀‬
H - C – O – C - H
‫׀‬ ‫׀‬
H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C - C – O - C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – O - C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
Structural formula – arrangement atoms in molecule (2D)
Hydrocarbon skeleton Functional gp
Display full SF Condensed SF Ball /stick model Spacefilling
ethanenitrile
H
‫׀‬
H - C – C ≡ N
‫׀‬
H
CH3CN
Structural formula – arrangement atoms in molecule (2D)
Display full SF Condensed SF Ball /stick model Spacefilling
methoxymethane
H H
‫׀‬ ‫׀‬
H - C – O – C - H
‫׀‬ ‫׀‬
H H
CH3–O– CH3
Hydrocarbon skeleton Functional gp

14. H H
‫׀‬ ‫׀‬
H - C – C – CI
‫׀‬ ‫׀‬
H H
Class Functional Prefix Example
Halogenoalkane F, CI, Br, I - chloro chloroethane
• member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n-1 X
Homologous Series
Class Functional Suffix Example Formula
Alcohol Hydroxyl - ol methanol CnH2n+1OH
• member differ by CH2 gp
• same functional group
• similar chemical properties
• chemical formula CnH2n+1OH
• end with ol
chloromethane chloroethane chloropropane
Number
carbon
IUPAC
name
Structure formula Molecular
formula
1 Methanol CH3OH CH3OH
2 Ethanol CH3CH2OH C2H5OH
3 Propanol CH3CH2CH2OH C3H7OH
4 Butanol CH3(CH2)2CH2OH C4H9OH
5 Pentanol CH3(CH2)3CH2OH C5H11OH
methanol ethanol propanol butanol
H
‫׀‬
H - C – OH
‫׀‬
H
H H
‫׀‬ ‫׀‬
H - C – C – OH
‫׀‬ ‫׀‬
H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬
H H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Hydrocarbon skeleton Functional gp
Structural formula – arrangement atoms in molecule (2D)
Ball /stick model SpacefillingCondensed SFDisplay full SF
CH3CI
chloromethane
Structural formula – arrangement atoms in molecule (2D)
Display full SF Condensed SF Ball /stick model Spacefilling
H H
‫׀‬ ‫׀‬
H - C – C – OH
‫׀‬ ‫׀‬
H H
CH3CH2OH
ethanol
H
‫׀‬
H - C – CI
‫׀‬
H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – CI
‫׀‬ ‫׀‬ ‫׀‬
H H H
Hydrocarbon skeleton Functional gp
Number
carbon
IUPAC name Structure formula Molecular
formula
1 chloromethane CH3CI CH3CI
2 chloroethane CH3CH2CI C2H5CI
3 chloropropane CH3CH2CH2CI C3H7CI
4 chlorobutane CH3(CH2)2CH2CI C4H9CI
5 chloropentane CH3(CH2)3CH2CI C5H11CI
H
‫׀‬
H - C – CI
‫׀‬
H

15. H CH3 CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C = C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C = C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
C – C – C – C – C = C
‫׀‬ ‫׀‬
CH3 CH3
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C = C - H
‫׀‬ ‫׀‬
H Br
H H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C = C – C – C - CI
‫׀‬ ‫׀‬ ‫׀‬
H H H
1 2 3 4 5
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CI - C – C = C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
C2H5
‫׀‬
CI – C = C – C – C – C
‫׀‬
C
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C = C – H
‫׀‬
CI
C2H5 H H
‫׀‬ ‫׀‬ ‫׀‬
C2H5 - C – C = C – H
‫׀‬
C2H5
H C2H5 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C = C – C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C = C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
IUPAC nomenclature
1 – chloropent-2-ene
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CI - C – C = C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
CH3(CH2)2CHCH2
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C = C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
Repeat CH2 x 2
CH3CH(CH3)CH2CHCH2
CH3 branch
CH3CH(CH3)CH=C(CH3)CH3
CH3 branch
3 -methylbut-1-ene
4 – methylhex-2-ene
2-chloro- 4-ethylhex-2-ene
3 2 1
4 3 2 1
3 - chloropropene
5-chloro-3-methylpent-2-ene 3 –bromobut-1-ene
4 3 2 1
3, 3-diethylpent-1-ene
Number from end of chain giving substituent lowest possible number
Alkene and Nomenclature
CI - substituent
6 5 4 3 2 12 3 4 5 6
1
Double bond
Alkene start from 2 carbon - ethene
1 2 3 4 5
1 2 3 4 5
1 – chloropent-2-ene
5 – chloropent- 4 -ene
Ethene/propene – no numbering needed
3, 5 – dimethylhex-1-ene
carbon IUPAC
name
Structure formula Molecular
formula
2 Ethene CH2=CH2 C2H4
3 Propene CH2=CHCH3 C3H6
4 Butene CH2=CHCH2CH3 C4H8
5 Pentene CH2=CH(CH2)2CH3 C5H10
4 3 2 1 3 2 1
CH3CH(CH3)CHC(CH3)CH3

16. H CH3 CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C = C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C = C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
C – C – C – C – C = C
‫׀‬ ‫׀‬
CH3 CH3
H CH3 CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C = C - H
‫׀‬ ‫׀‬
H CH3
H H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C = C – C – C - F
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
1 2 3 4 5
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CI - C – C = C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
C2H5
‫׀‬
Br – C - C – C – C – C
‖
C
CH3 H H
‫׀‬ ‫׀‬ ‫׀‬
CH3 - C – C = C – H
‫׀‬
H
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C = C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
IUPAC nomenclature
1 – chloropent-2-ene
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CI - C – C = C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
CH3(CH2)2CHCH2
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C = C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
Repeat CH2 x 2
CH3CH(CH3)CH2CHCH2
CH3 branch
CH3CH(CH3)CHC(CH3)CH3
CH3 branch
2- methylbut-2-ene
3-methylpent-1-ene
2-bromo- 3-ethylhex-1-ene
4 3 2 1
3 2 1
2, 3 –dimethylbut-2-ene
5-fluoro-3,4-dimethylpent-2-ene 2, 3, 3 trimethylbut-1-ene
4 3 2 1
3-methylbut-1-ene
Number from end of chain giving substituent lowest possible number
Alkene and Nomenclature
CI - substituent
6 5 4 3 2 12 3 4 5 6
1
Double bond
Alkene start from 2 carbon - ethene
1 2 3 4 5
1 2 3 4 5
1 – chloropent-2-ene
5 – chloropent- 4 -ene
Ethene/propene – no numbering needed
3, 5 – dimethylhex-1-ene
carbon IUPAC
name
Structure formula Molecular
formula
2 Ethene CH2CH2 C2H4
3 Propene CH2=CHCH3 C3H6
4 Butene CH2=CHCH2CH3 C4H8
5 Pentene CH2=CH(CH2)2CH3 C5H10
1 2 3 4
CH3 H
‫׀‬ ‫׀‬
CH3 - C = C - C – H
‫׀‬ ‫׀‬
H CH3
1 2 3 4
C – C
‫׀‬
CH3 – C – C = C
4 5
CH3CH(CH3)CH=C(CH3)CH3

17. H CH3 H CH3 O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H H O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
C
‫׀‬
C – C – C – C – C – C
‫׀‬
H- C=O
H H O
‫׀‬ ‫׀‬ ‖
H - C – C – C – H
‫׀‬ ‫׀‬
CI CI
H H O
‫׀‬ ‫׀‬ ‖
H - C – C – C – H
‫׀‬ ‫׀‬
CI Br
C2H5 O
‫׀‬ ‖
C2H5 - C – C – H
‫׀‬
C2H5
O C2H5 H H H
‖ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H O
‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
IUPAC nomenclature
2 – chloropropanal
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
H CI O
‫׀‬ ‫׀‬ ‖
H - C – C – C - O
‫׀‬ ‫׀‬
H H C1 – functional gp
(numbering start here)
C2 – substituent gp - CI
CH3(CH2)3CHO
H H H H O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Repeat CH2 x 3
CH3CH(CH3)(CH2)2CHO
Repeat CH2 x 2CH3 branch
CH3CH(CH3)CH2CH(CH3)CHO
CH3 branch
3 - methylbutanal
2 - ethylpentanal
2-ethyl- 4-methylpentanal
12
2 3 4 51
1
1
2
3 2
3 - chloro- 2- bromopropanal
2, 3 - dichloropropanal
O H H H
‖ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬
OH H H
O H H H
‖ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C = C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
But – 3 –en-1-al
2 -hydroxybutanal
1 2 3 4
2, 2 - diethylbutanal
3
Number from end of chain giving substituent lowest possible number
Aldehyde and Nomenclature
carbon IUPAC
name
Structure formula Molecular
formula
1 Methanal HCHO CH2O
2 Ethanal CH3CHO C2H4O
3 Propanal CH3CH2CHO C3H6O
4 Butanal CH3(CH2)2CHO C4H8O
5 Pentanal CH3(CH2)3CHO C5H10O
4 3 2 1
3 2 1
3 -hydroxypropanal
functional gp aldehyde – at the end
OH - substituent
3 -aldehydepropanol
1 2 3 4
2 3 4 5
1
Double bond
(3 – butenal)
CHO – functional gp, not OH
3 2 1
H H O
‫׀‬ ‫׀‬ ‖
HO - C – C – C – H
‫׀‬ ‫׀‬
H H

18. H CH3 CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‖ ‫׀‬ ‫׀‬
H H O H H
H CH3 H O H
‫׀‬ ‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H O H H H
‫׀‬ ‖ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C – C – C = C - H
‫׀‬ ‫׀‬
H H
H H O H
‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬
H OH H
H O H H H
‫׀‬ ‖ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
1 2 3 4 5
H O H H H
‫׀‬ ‖ ‫׀‬ ‫׀‬ ‫׀‬
CI - C – C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
O C2H5
‖ ‫׀‬
CI – C – C – C – C – C
‫׀‬
C
H O H
‫׀‬ ‖ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬
CI H
C2H5 O H
‫׀‬ ‖ ‫׀‬
C2H5 - C – C – C – H
‫׀‬ ‫׀‬
C2H5 H
H C2H5 O H H
‫׀‬ ‫׀‬ ‖ ‫׀‬ ‫׀‬
H - C – C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 O H
‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C – C – C – C – H
‫׀‬ ‫׀‬
H H
IUPAC nomenclature
1 – chloropentan- 2-one
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
H O H H H
‫׀‬ ‖ ‫׀‬ ‫׀‬ ‫׀‬
CI - C – C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
CH3(CH2)2COCH3
H H H O H
‫׀‬ ‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Repeat CH2 x 2
CH3CH(CH3)CH2COCH3
CH3 branch
CH3CH(CH3)COCH(CH3)CH3
CH3 branch
3 - methylbutanone
4 – methylhexan–3-one
2-chloro- 4-ethylhexan-3-one
3 2 1
4 3 2 1
1 - chloropropanone
pentan-2-one
3 -hydroxybutanone
4 3 2 1
3, 3 – diethylpentan-2-one
Number from end of chain giving substituent lowest possible number
Ketone and Nomenclature
functional gp ketone – inside carbon chain
CI - substituent
1 2 3 4 5
2 3 4 5 6
1
Double bond
Ketone start from 3 carbon - propanone
carbon IUPAC name Structure formula Molecular
formula
3 Propanone CH3COCH3 C3H6O
4 Butanone CH3COCH2CH3 C4H8O
5 Pentanone CH3CH2COCH2CH3 C5H10O
6 Hexanone CH3CH2COCH2CH2CH3 C6H12O
1 2 3 4 5
1 2 3 4 5
1 – chloropentan- 2 -one
5 – chloropentan- 4 -one
Propanone/Butanone – no numbering needed
Pent-4-en-2-one
CO – functional gp, not OH
4 3 2 1 1 2 3

19. H OH H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H CH3 H CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C - C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H OH H H
H CH3 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C - C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CI - C – C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
C – C – C – C = C
‫׀‬
OH
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
OH H OH
H H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C - C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H OH CH3 H H
1 2 3 4 5
CH3
‫׀‬
HO– C – C – C
‫׀‬
C
H H OH
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – C - OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H CH3 H H H
H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
OH H H H
IUPAC nomenclature
5–chloropent-4-ene-1-ol
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CI - C = C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬
H H H
CH3(CH2)2CH(OH)CH3
H H H OH H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
Repeat CH2 x 2
CH3CH(CH3)(CH2)2CH2OH
CH3 branch
CH3CH(CH3)CH(OH)CH(CH3)CH3
CH3 branch
2- methylbutan-1-ol
4 – methylpentan-1-ol
2- methylbutan--2-ol
3 2 1
5 4 3 2 1
2- methylpropan-1-ol
3,3 -dimethylpentan-2-ol propane-1,2-diol
1 2 3
Number from end of chain giving substituent lowest possible number
Alcohol and Nomenclature
CI - substituent
1 2 3 4 52 3 4
1 Double bond
5 4 3 2 1
5– chloropentan-1-ol
1– chloropentan-5-ol
Methanol/Ethanol – no numbering needed
pen-4-ene-2-ol
1 2 3 4 3 2 1
5 4 3 2 1
Repeat CH2 x 2
carbon IUPAC
name
Structure formula Molecular
formula
1 Methanol CH3OH CH3OH
2 Ethanol CH3CH2OH C2H5OH
3 Propanol CH3CH2CH2OH C3H7OH
4 Butanol CH3(CH2)2CH2OH C4H9OH
5 Pentanol CH3(CH2)3CH2OH C5H11OH
OH – functional gp, not alkene
2- methylpropan-2-ol
OH – functional gp, not alkene

20. H CH3 H CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C - C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H OH H H
H CH3 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C - C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CI - C – C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
OH
‫׀‬
C – C – C – C – C = C
‫׀‬ ‫׀‬
CH3 CH3
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C = C - H
‫׀‬ ‫׀‬
H OH
H H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C - C – C – C - CI
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H OH H H H
1 2 3 4 5
OH C2H5
‫׀‬ ‫׀‬
CI – C - C – C – C – C
‫׀‬
C
H H OH
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
CI H H
C2H5 H H
‫׀‬ ‫׀‬ ‫׀‬
C2H5 - C – C - C – OH
‫׀‬
C2H5
H C2H5 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H OH H H
H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬ l
H H OH H
IUPAC nomenclature
5–chloropent-4-ene-1-ol
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CI - C = C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬
H H H
CH3(CH2)2CH(OH)CH3
H H H OH H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
Repeat CH2 x 2
CH3CH(CH3)(CH2)2CH2OH
CH3 branch
CH3CH(CH3)CH(OH)CH(CH3)CH3
CH3 branch
3 – methylbutan-2-ol
4 – methylhexan-3-ol
2-chloro-4-ethylhexan-2-ol
3 2 1
4 3 2 1
3 – chloropropan-1-ol
5-chloro-3-methylpentan-2-ol But-3-ene-2-ol
1 2 3 4
3, 3 – diethylpentan-1-ol
Number from end of chain giving substituent lowest possible number
Alcohol and Nomenclature
CI - substituent
6 5 4 3 2 12 3 4 5 6
1
Double bond
5 4 3 2 1
5– chloropentan-1-ol
1– chloropentan-5-ol
Methanol/Ethanol – no numbering needed
3, 5 – dimethylhex-1-ene-3-ol
4 3 2 1 3 2 1
5 4 3 2 1
Repeat CH2 x 2
carbon IUPAC
name
Structure formula Molecular
formula
1 Methanol CH3OH CH3OH
2 Ethanol CH3CH2OH C2H5OH
3 Propanol CH3CH2CH2OH C3H7OH
4 Butanol CH3(CH2)2CH2OH C4H9OH
5 Pentanol CH3(CH2)3CH2OH C5H11OH
OH – functional gp, not alkene

21. H CH3 H CH3 O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H H O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
C
‫׀‬
C – C – C – C – C – C
‫׀‬
COOH
H H O
‫׀‬ ‫׀‬ ‖
H - C – C – C – OH
‫׀‬ ‫׀‬
CI CI
H H O
‫׀‬ ‫׀‬ ‖
H - C – C – C – OH
‫׀‬ ‫׀‬
CI Br
C2H5 O
‫׀‬ ‖
C2H5 - C – C – OH
‫׀‬
C2H5
O C2H5 H H H
‖ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
HO- C – C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H O
‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬
H H H
IUPAC nomenclature
2 – chloropropanoic acid
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
C1 – functional gp
(numbering start here)
C2 – substituent gp - CI
CH3(CH2)3COOH
H H H H O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Repeat CH2 x 3
CH3CH(CH3)(CH2)2COOH
Repeat CH2 x 2CH3 branch
CH3CH(CH3)CH2CH(CH3)COOH
CH3 branch
3-methylbutanoic acid
2 -ethylpentanoic acid
2-ethyl-4-methylpentanoic acid
12
2 3 4 51
1
1
2
3 2
3 - chloro- 2- bromopropanoic acid
2, 3 – dichloropropanoic acid
O H H H
‖ ‫׀‬ ‫׀‬ ‫׀‬
HO- C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬
OH H H
O H H H
‖ ‫׀‬ ‫׀‬ ‫׀‬
HO- C – C – C = C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
But -3 –enoic acid
2 –hydroxybutanoic acid
1 2 3 4
2, 2 – diethylbutanoic acid
3
Number from end of chain giving substituent lowest possible number
Carboxylic acid and Nomenclature
4 3 2 1
3 2 1
3 –hydroxypropanoic acid
functional gp acid – at the end
OH - substituent
1 2 3 4
2 3 4 5
1
Double bond
(3 – butenoic acid)
COOH – functional gp, not OH
carbon IUPAC name Structure formula Molecular
formula
1 Methanoic acid HCOOH HCOOH
2 Ethanoic acid CH3COOH CH3COOH
3 Propanoic acid CH3CH2COOH C2H5COOH
4 Butanoic acid CH3(CH2)2COOH C3H7COOH
5 Pentanoic acid CH3(CH2)3COOH C4H9COOH
3 2 1
H H O
‫׀‬ ‫׀‬ ‖
HO - C – C – C – OH
‫׀‬ ‫׀‬
H H
H CI O
‫׀‬ ‫׀‬ ‖
H - C – C – C - OH
‫׀‬ ‫׀‬
H H

22. H CH3 H CH3 O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H H O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
C
‫׀‬
C – C – C – C – C – C
‫׀‬
COOH
H H O
‫׀‬ ‫׀‬ ‖
H - C – C – C – OH
‫׀‬ ‫׀‬
Br H
H H O
‫׀‬ ‫׀‬ ‖
H - C – C – C – OH
‫׀‬ ‫׀‬
H CH3
CH3 O
‫׀‬ ‖
CH3 - C – C – C – OH
‫׀‬
CH3
O H H H OH
‖ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
HO- C – C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H O
‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬
H H CH3
IUPAC nomenclature
2 – chloropropanoic acid
Systematic naming organic molecules
Prefix Stem Suffix
Position and
substituent
Longest carbon
chain
Functional
gp
H CI O
‫׀‬ ‫׀‬ ‖
H - C – C – C - OH
‫׀‬ ‫׀‬
H H C1 – functional gp
(numbering start here)
C2 – substituent gp - CI
CH3(CH2)3COOH
H H H H O
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‖
H - C - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Repeat CH2 x 3
CH3CH(CH3)(CH2)2COOH
Repeat CH2 x 2CH3 branch
CH3CH(CH3)CH2CH(CH3)COOH
CH3 branch
2, 3 -dimethylbutanoic acid
5 – hydroxypentanoic acid
2-ethyl- 4-methylpentanoic acid
12
2 3 4 51
1
1
2
3 2
2- methylpropanoic acid
3- bromopropanoic acid
O H H O
‖ ‫׀‬ ‫׀‬ ‖
HO- C – C – C – C -OH
‫׀‬ ‫׀‬
H H
O H H H
‖ ‫׀‬ ‫׀‬ ‫׀‬
HO- C – C – C = C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
But – 3 –enoic acid
Butanedioic acid
1 2 3 4
3, 3 -dimethylbutanoic acid
3
Number from end of chain giving substituent lowest possible number
Carboxylic acid and Nomenclature
4 3 4 3 2 1
3 2 1
3 –hydroxypropanoic acid
functional gp acid – at the end
OH - substituent
1 2 3 4
2 3 4 5
1
Double bond
(3 – butenoic acid)
carbon IUPAC name Structure formula Molecular
formula
1 Methanoic acid HCOOH HCOOH
2 Ethanoic acid CH3COOH CH3COOH
3 Propanoic acid CH3CH2COOH C2H5COOH
4 Butanoic acid CH3(CH2)2COOH C3H7COOH
5 Pentanoic acid CH3(CH2)3COOH C4H9COOH
H H O
‫׀‬ ‫׀‬ ‖
HO - C – C – C – OH
‫׀‬ ‫׀‬
H H
(1, 4 butanedioic acid)
3 2 1

23. H O H H H
‫׀‬ ‖ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C –O – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H O H H H
‫׀‬ ‖ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – O – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – O – C – H
‫׀‬ ‫׀‬ ‖ ‫׀‬
H H O H
H CH3 H O H
‫׀‬ ‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C - C – C – C – O – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H O
‫׀‬ ‖
H – C – C – O – C – C - C – C
‫׀‬ ‫׀‬
H C
H H O H
‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C – C – C – O – C- H
‫׀‬ ‫׀‬ ‫׀‬
H H H
H O H H
‫׀‬ ‖ ‫׀‬ ‫׀‬
H – C- O – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
O
‖
C – C – C – O – C – C – C
‫׀‬
C
H O H
‫׀‬ ‖ ‫׀‬
H - C – C – O - C – H
‫׀‬ ‫׀‬
H H
CH3 O H
‫׀‬ ‖ ‫׀‬
C2H5 - C – C – O - C – H
‫׀‬ ‫׀‬
CH3 H
H C2H5 O H H
‫׀‬ ‫׀‬ ‖ ‫׀‬ ‫׀‬
H - C – C – C– O - C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 O H
‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C – C – C – O - C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
IUPAC nomenclature
Propyl ethanoate
Systematic naming organic molecules
Ethanoate Propyl
(Ethanoic acid) (Propanol)
CH3(CH2)2COOCH3
H H H O H
‫׀‬ ‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C - C – C – C – O– C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Repeat CH2 x 2
CH3CH(CH3)CH2COOCH3
CH3 branch
CH3CH(CH3)COOCH3
CH3 branch
Methyl 2-methylpropanoate
Ethyl 2-methylbutanoate
Propyl 2-methylpropanoate
Methyl ethanoate
Methyl propanoate (same structure)
Methyl 2,2 dimethylbutanoate
Ester and Nomenclature
Ethyl propanoate
2-methylbutyl ethanoate
IUPAC name Structure formula Molecular
formula
Methyl methanoate HCOOCH3 R–COO-R
Methyl ethanoate CH3COOCH3 R–COO-R
Methyl propanoate CH3CH2COOCH3 R–COO-R
Methyl butanoate CH3CH2CH2COOCH3 R–COO-R
Propyl ethanoate
Ethanoate = Acetate
Propyl acetate

24. H H H H H
‫׀‬ l ‫׀‬ ‫׀‬ ‫׀‬
H - C – C –O – C – C – C – H
‫׀‬ l ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H H H H H
‫׀‬ l ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – O – C – C – C – H
‫׀‬ l ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – O – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H CH3 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C – O – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H
‫׀‬
H – C – C – O – C – C - C – C – C
‫׀‬ ‫׀‬
H C
H H H H
‫׀‬ ‫׀‬‫׀‬‫׀‬
H - C – C – C – O – C- H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H – C- O – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
C – C – C – C – O – C – C
‫׀‬
C
H H H
‫׀‬‫׀‬‫׀‬
H - C – C – O - C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
CH3 H H
‫׀‬‫׀‬‫׀‬
C2H5 - C – C – O - C – H
‫׀‬ ‫׀‬ ‫׀‬
CH3 H H
H C2H5 H H H
‫׀‬ ‫׀‬‫׀‬‫׀‬ ‫׀‬
H - C – C – C– O - C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H CH3 H H
‫׀‬ ‫׀‬‫׀‬‫׀‬
H - C – C – C – O - C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
IUPAC nomenclature
Ethoxy propane
Systematic naming organic molecules
Ethoxy Propane
(Ethane)
CH3(CH2)2CH2OCH3
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C –O – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
Repeat CH2 x 2
CH3CH(CH3)CH2CH2OCH3
CH3 branch
CH3CH(CH3)CH2OCH3
CH3 branch
Methoxy 2-methylpropane
Ethoxy 2-methylbutane
Ethoxy 2-methylbutane
Methoxy ethane
Methoxy propane (same structure)
Methoxy 2,2-dimethylbutane
Ether and Nomenclature
Propoxy ethane
Ethoxy 2-methylpentane
Ethyl Propyl ether
IUPAC name Structure formula Molecular
formula
Methoxymethane CH3 - O – CH3 R –O -R
Methoxyethane CH3CH2 - O – CH3 R –O -R
Methoxypropane CH3CH2CH2 - O –CH3 R –O -R
Methoxybutane CH3(CH2 )3 - O –CH3 R –O -R
Click here, diff naming system ether
Ethoxy propane
Shorter carbon 1st
Longer carbon 2nd

25. H H H CI H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C – C – H
l l ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H Br H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H CH3 H CH3 H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C - C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H CI H H
H CH3 H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C - C – CI
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
CI - C – C – C – C = C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
C – C – C – C = C
‫׀‬
CI
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
CI H CI
H H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C - C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H CI CH3 H H
1 2 3 4 5
CH3
‫׀‬
CI – C – C – C
‫׀‬
C
H H CI
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – C - F
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H CH3 H H H
H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
I H H H
IUPAC nomenclature
2–chloropentane
Systematic naming organic molecules
Prefix Stem
Position and
functional gp
Longest carbon
chain
CH3(CH2)2CH(CI)CH3
H H H CI H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C - C – C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H H
Repeat CH2 x 2
CH3CH(CH3)(CH2)2CH2CI
CH3 branch
CH3CH(CH3)CH(CI)CH(CH3)CH3
CH3 branch
1-iodo-2-methylbutane
1-fluoro-4–methylpentane
2-chloro-2-methylbutane
3 2 1
5 4 3 2 1
1-chloro-2-methylpropane
2-chloro-3,3-dimethylpentane 1,3-dichloropropane
1 2 3
Number from end of chain giving substituent lowest possible number
Halogenoalkane and Nomenclature
CI - halogen
5 4 3 2 12 3 4
1 Double bond
5 4 3 2 1
5– chloropent- 1-ene
1– chloropent-4-ene
4-chloropen-1-ene
1 2 3 4 3 2 1
5 4 3 2 1
Repeat CH2 x 2
2-bromo-2-methylpropane
C=C – functional gp, not halogen
carbon IUPAC name Structure formula Molecular
formula
1 chloromethane CH3CI CH3CI
2 chloroethane CH3CH2CI C2H5CI
3 chloropropane CH3CH2CH2CI C3H7CI
4 chlorobutane CH3(CH2)2CH2CI C4H9CI
5 chloropentane CH3(CH2)3CH2CI C5H11CI

26. Nomenclature for Organic Molecule (Alkane)
C – C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH2 CH3
4- ethyl-2-methylhexane
1 2 3 4 5 6
3- ethyl- 5-methylhexane
wrong
C – C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH2 CH3
6 5 4 3 2 1
Number from end giving substituent lowest possible number
2, 3 -dimethylpentane
C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH3
1 2 3 4 5
4-ethyl- 2, 3, 6 -trimethyloctane
CH2CH3
‫׀‬
C – C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3
1 2 3 4 5 6 7 8
1 2
2, 2, 4-trimethylpentane
CH3
‫׀‬
C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH3
5 4 3 2 1
C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3
‫׀‬
CH3
3 -ethyl-2, 5-dimethylheptane
1 2 3 4 5 6 7
3 4
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H- C-H H
‫׀‬
H
H H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H-C – C – C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H- C-H H H
‫׀‬
H- C- H
‫׀‬
H- C- H
‫׀‬
H
2-methylpropane 4 -ethylheptane
1 2 3
1 2 3 4
C
‫׀‬
C – C – C – C – C – C
‫׀‬ ‫׀‬
C C
‫׀‬
C
‫׀‬
C
4- ethyl -2, 2- dimethylheptane
C
‫׀‬
C C
‫׀‬ ‫׀‬
C – C – C – C – C – C – C
‫׀‬
C
‫׀‬
C
4-ethyl-3, 5- dimethyloctane
1 2 3 4
1
2
348 7 6 5
5
Give IUPAC names for alkanes
CH3CH2CH(CH3)2 (CH3)3 – C – C2H5
2 methylbutane
CH(C2H5)3 CH(C3H7)3
2,2 - dimethylbutane 3-ethylpentane 4-propylheptane
6
5
6
7
5
6
7

27. Nomenclature for Organic Molecule (Alkane)
C – C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH2 CH3
4- ethyl-2-methylhexane
1 2 3 4 5 6
3- ethyl- 5-methylhexane
wrong
C – C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH2 CH3
6 5 4 3 2 1
Number from end giving substituent lowest possible number
2, 3 - dimethylpentane
C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH3
1 2 3 4 5
4 -ethyl- 2, 3, 6 -trimethyloctane
CH2CH3
‫׀‬
C – C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3
1 2 3 4 5 6 7 8
1 2
2, 2, 4 - trimethylpentane
CH3
‫׀‬
C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH3
5 4 3 2 1
C – C – C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3
‫׀‬
CH3
3 -ethyl -2, 5- dimethylheptane
1 2 3 4 5 6 7
3 4
Give IUPAC names for following molecule
CH3CH2CH(CH3)2
2-methylbutane
(CH3)3CC2H5
2,2 - dimethylbutane
CH(C2H5)3
3-ethylpentane
CH(C3H7)3
4-propylheptane
(CH3 )3C-Br
2-bromo-2-methylpropane
CH3CH=C(CH3)2
2-methylbut-2-ene
(CH3)3C-CH=CH2
3, 3-dimethylbut-1-ene
CH2=C(CH3)CH=CH2
2-methylbut-1,3-diene
CH2=CH-CH=CH2
but-1,3-diene
(CH3)2CH-CH=CH2
3-methylbut-1-ene
CH2 =C(CH3)2
2-methylpropene
CH3-CH(CH3)COCH2CH3
2 -methylpentan-3-one
CH3(CH2)2CH2NH2
butanamine
3
CH3(CH2)2COOCH2CH3
ethyl butanoate
CH3(CH2)2OCH3
methoxypropane

28. Nomenclature for Organic Molecules (Alkene)
C – C = C – C – C – C
‫׀‬ ‫׀‬
CH3 CH2 CH3
4- ethyl-2-methylhex-2-ene
1 2 3 4 5 6
3- ethyl- 5-methylhex-4-ene
wrong
C – C = C – C – C – C
‫׀‬ ‫׀‬
CH3 CH2 CH3
6 5 4 3 2 1
Number from end giving substituent lowest possible number
2, 3 -dimethylpent-2-ene
C – C = C – C – C
‫׀‬ ‫׀‬
CH3 CH3
1 2 3 4 5
4 -ethyl- 2, 3, 6 -trimethyloct-3-ene
CH2CH3
‫׀‬
C – C – C = C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3
1 2 3 4 5 6 7 8
1 2
2, 2, 4 -trimethylpent-1-ene
CH3
‫׀‬
C – C – C – C = C
‫׀‬ ‫׀‬
CH3 CH3
5 4 3 2 1
C – C – C = C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3
‫׀‬
CH3
3 -ethyl -2, 5- dimethylhept-3-ene
1 2 3 4 5 6 7
3 4
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C = C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H- C-H H
‫׀‬
H
H H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H-C – C – C = C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H- C-H H H
‫׀‬
H- C- H
‫׀‬
H- C- H
‫׀‬
H
2-methylpropene 4 – ethylhept-3-ene
1 2 3 4
C
‫׀‬
C = C – C – C – C – C
‫׀‬ ‫׀‬
C C
‫׀‬
C
‫׀‬
C
4- ethyl -2, 2- dimethylhept-1-ene
C
‫׀‬
C C
‫׀‬ ‫׀‬
C – C – C – C – C = C – C
‫׀‬
C
‫׀‬
C
4-ethyl-3, 5- dimethyloct-3-ene
1 2 3 4
1
2
348 7 6 5
5
Give IUPAC names for alkenes
CH3CH=C(CH3)2 (CH3)3C-CH=CH2
2 methylbut-2-ene
CH2=CH-CH=CH2
3, 3- dimethylbut-1-ene 2-methylbut-1,3-diene but-1,3-diene
6
No numbering needed
1 2 3 4
CH2=C(CH3)CH=CH2
5
6
7
5
6
7

29. Nomenclature for Organic Molecules (Alkene)
C – C = C – C – C – C
‫׀‬ ‫׀‬
CH3 CH2 CH3
4- ethyl- 2-methylhex-2-ene
1 2 3 4 5 6
3- ethyl- 5-methylhex-4-ene
wrong
C – C = C – C – C – C
‫׀‬ ‫׀‬
CH3 CH2 CH3
6 5 4 3 2 1
Number from end giving substituent lowest possible number
2, 3 -dimethylpent-2-ene
C – C = C – C – C
‫׀‬ ‫׀‬
CH3 CH3
1 2 3 4 5
4 -ethyl- 2, 3, 6 -trimethyloct-3-ene
CH2CH3
‫׀‬
C – C – C = C – C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3
1 2 3 4 5 6 7 8
1 2
2, 2, 4 -trimethylpent-1-ene
CH3
‫׀‬
C – C – C – C = C
‫׀‬ ‫׀‬
CH3 CH3
5 4 3 2 1
C – C – C = C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
CH3 CH2 CH3
‫׀‬
CH3
3 -ethyl -2, 5- dimethylhept-3-ene
1 2 3 4 5 6 7
3 4
5
Give IUPAC names for following molecule
CH3CHBrCH2CH2OH
3- bromobutan-1-ol
CH3-CH(OH)-CH3
propan-2–ol
CH3CH(OH)-CH2CH3
butan-2-ol
(CH3)2C(OH)CH2CH3
2-methylbutan-2-ol
(CH3)2CHCH2OH
2-methylpropan-1-ol
CH3CH2CH(CH3)OH
(CH3 )3C-OH
2-methylpropan-2-ol
CH3-CH2CH(CH3)CHO
2-methylbutanal
(CH3)2CHCH(CH3)CHO
2,3 -dimethylbutanal
CH3(CH2)2CH(CH3)COCH3
3-methylhexan-2-one
CH3CH2CH(CI)CH(CI)COOH
2, 3-dichloropentanoic acid
CH3(CH2)2COOH
butanoic acid
HO-C(CH3)2CH2CH2-COOH
4- hydroxy-4-methylpentanoic acid
CH3(CH2)2CH(CH3)CH(CH3)COOH
2, 3-dimethylhexanoic acid
CH3-C(CH3)2-CH2CHO
3, 3-dimethylbutanal

30. H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – C – F
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H CH3 H H H
H CH3
‫׀‬ ‫׀‬
CI – C – C – C
‫׀‬ ‫׀‬
H CH3
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – Br
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
I H H H
H C
‫׀‬ ‫׀‬
C – C – C – C - C
‫׀‬
CI
C CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
CI H H
CH3
‫׀‬
CI – C – C – C
‫׀‬
H
H H CI
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
Halogenoalkane and Nomenclature
H
‫׀‬
CH3 – C – CI
‫׀‬
H
Types of halogenoalkane
Primary 1 0
NO alkyl /1 alkyl/R gp bond to C attach to halogen
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – CI
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H
‫׀‬
H - C – CI
‫׀‬
H
Secondary 2 0
2 alkyl/R gp bond to C attach to halogen
H
‫׀‬
CH3 – C – CI
‫׀‬
CH3
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H CI H
H
‫׀‬
R – C – CI
‫׀‬
R
Tertiary 3 0
3 alkyl/R gp bond to C attach to halogen
CH3
‫׀‬
CH3 – C – CI
‫׀‬
CH3
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H CI H
R
‫׀‬
R – C – CI
‫׀‬
R
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H CI H
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
H CI H
CH3
‫׀‬
CH3 – C – CI
‫׀‬
CH3
C CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H Br H
CH3
‫׀‬
CI – C – C – C
‫׀‬
C – C
Br CH3
‫׀‬ ‫׀‬
C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH3
C CI C
‫׀‬ ‫׀‬ ‫׀‬
C – C – C – C – C
‫׀‬
C
Primary 1 o
Secondary 2 o
Tertiary 3 o
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H H F
H H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C - C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H CI CH3 H H
H
‫׀‬
CH3 – C – CI
‫׀‬
CH3

31. CH3
‫׀‬
HO – C – C – C
‫׀‬
C – C
H CH3
‫׀‬ ‫׀‬
HO – C – C – C
‫׀‬ ‫׀‬
H CH3
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H CH3 H H H
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
OH H H H
H C
‫׀‬ ‫׀‬
C – C – C – C - C
‫׀‬
OH
C CH3
‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
OH H H
CH3
‫׀‬
HO – C – C – C
‫׀‬
H
H H OH
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
Alcohol and Nomenclature
H
‫׀‬
CH3 – C – OH
‫׀‬
H
Types of alcohol
Primary 1 0
NO alkyl /1 alkyl/R gp bond to C attach to OH
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H
‫׀‬
H - C – OH
‫׀‬
H
Secondary 2 0
2 alkyl/R gp bond to C attach to OH
H
‫׀‬
CH3 – C – OH
‫׀‬
CH3
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H OH H
H
‫׀‬
R – C – OH
‫׀‬
R
Tertiary 3 0
3 alkyl/R gp bond to C attach to OH
CH3
‫׀‬
CH3 – C – OH
‫׀‬
CH3
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H OH H
R
‫׀‬
R – C – OH
‫׀‬
R
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H OH H
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
H OH H
CH3
‫׀‬
CH3 – C – OH
‫׀‬
CH3
C CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H OH H
OH CH3
‫׀‬ ‫׀‬
C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH3
C OH C
‫׀‬ ‫׀‬ ‫׀‬
C – C – C – C – C
‫׀‬
C
Primary 1 o
Secondary 2 o
Tertiary 3 o
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H H OH
H H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C - C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H OH CH3 H H
H
‫׀‬
CH3 – C – OH
‫׀‬
CH3

32. H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – C –NH2
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H CH3 H H H
H CH3
‫׀‬ ‫׀‬
NH2 – C – C – C
‫׀‬ ‫׀‬
H CH3
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – NH2
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
NH2 H H H
H C
‫׀‬ ‫׀‬
C – C – C – C - C
‫׀‬
NH2
C CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
NH2 H H
CH3
‫׀‬
NH2 – C – C – C
‫׀‬
H
H H NH2
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
Amines and Nomenclature
H
‫׀‬
CH3 – C – NH2
‫׀‬
H
Types of amines
Primary 1 0
NO alkyl /1 alkyl/R gp bond to C attach to nitrogen
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – NH2
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
H
‫׀‬
H - C – NH2
‫׀‬
H
Secondary 2 0
2 alkyl/R gp bond to C attach to nitrogen
H
‫׀‬
CH3 – C – NH2
‫׀‬
CH3
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H NH2 H
H
‫׀‬
R – C – NH2
‫׀‬
R
Tertiary 3 0
3 alkyl/R gp bond to C attach to nitrogen
CH3
‫׀‬
CH3 – C – NH2
‫׀‬
CH3
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H NH2 H
R
‫׀‬
R – C – NH2
‫׀‬
R
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H NH2 H
H CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬
H NH2 H
CH3
‫׀‬
CH3 – C – NH2
‫׀‬
CH3
C CH3 H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H NH2 H
CH3
‫׀‬
NH2 – C – C – C
‫׀‬
C – C
NH2 CH3
‫׀‬ ‫׀‬
C – C – C – C – C
‫׀‬ ‫׀‬
CH3 CH3
C NH2 C
‫׀‬ ‫׀‬ ‫׀‬
C – C – C – C – C
‫׀‬
C
Primary 1 o
Secondary 2 o
Tertiary 3 o
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C - C – H
‫׀‬ ‫׀‬ ‫׀‬
H H NH2
H H CH3 H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H – C – C - C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H NH2 CH3 H H
H
‫׀‬
CH3 – C – NH2
‫׀‬
CH3

33. Acknowledgements
Thanks to source of pictures and video used in this presentation
Thanks to Creative Commons for excellent contribution on licenses
http://creativecommons.org/licenses/
Prepared by Lawrence Kok
Check out more video tutorials from my site and hope you enjoy this tutorial
http://lawrencekok.blogspot.com