ib chemistry on organic nomenclature and functional groups

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

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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

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


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



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 2 CH3 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

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



Prefix Stem Suffix

Position and

substituent

Longest carbon

chain

Functional

gp

H CI O ‖ ׀ ׀

H - C – C – C - OH



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


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 5 1

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

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 number 3

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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• 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

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



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

• member differ by CH2 gp • same functional group • similar chemical properties • chemical formula CnH2n+2

• end with ane



Homologous Series


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




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 Structural formula – arrangement atoms in molecule

Display full SF Condensed SF Ball /stick model Spacefilling

ethane

CH3CH3

H H

׀ ׀

H - C – C – H

׀ ׀

H H

propene


H H H

׀ ׀ ׀

C = C – C - H

׀ ׀

H H

CH2=CHCH3

• member differ by CH2 gp • same functional group • similar chemical properties • chemical formula CnH2n-2

• end with yne


Alkyne C ≡ C - yne ethyne CnH2n-2

Homologous Series


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


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


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

Ball /stick model Spacefilling Condensed SF Display full SF

H

׀

H - C ≡ C – C – H

׀

H

CH≡C-CH3

propyne



H H

׀ ׀

H - C – C – OH

׀ ׀

H H

CH3CH2OH

ethanol

• member differ by CH2 gp • same functional group • similar chemical properties • chemical formula CnH2nO

• end with one


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


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


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 Structural formula – arrangement atoms in molecule

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

• member differ by CH2 gp • same functional group • similar chemical properties • chemical formula CnH2n+1COOH

• end with oic acid


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


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


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




O

‖

H - C - O H

methanoic acid

HCOOH




O H

׀ ‖

H - C – O – C - H

׀

H

HCOOCH3

Methyl methanoate

• member differ by CH2 gp • same functional group • similar chemical properties • chemical formula CnH2n+1NH2

• end with amine


Amine NH2 - amine ethanamine CnH2n+1NH2

Homologous Series


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


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


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




methanamine

H H

׀ ׀

H - C – N - H

׀

H

CH3NH2




methanamide

O H

׀ ‖

H - C – N - H

HCONH2

• member differ by CH2 gp • same functional group • similar chemical properties • chemical formula CnH2n+1CN

• end with nitrile


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


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


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




ethanenitrile

H

׀

H - C – C ≡ N

׀

H

CH3CN



methoxymethane

H H

׀ ׀

H - C – O – C - H

׀ ׀

H H

CH3–O– CH3


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


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







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



Ball /stick model Spacefilling Condensed SF Display full SF

CH3CI

chloromethane



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


Number carbon


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

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


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


Alkene and Nomenclature

CI - substituent

6 5 4 3 2 1 2 3 4 5 6

1

Double bond

Alkene start from 2 carbon - ethene

1 2 3 4 5

1 2 3 4 5


5 – chloropent- 4 -ene

Ethene/propene – no numbering needed

3, 5 – dimethylhex-1-ene


2 Ethene CH2=CH2 C2H4




4 3 2 1 3 2 1

CH3CH(CH3)CHC(CH3)CH3

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



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


Alkene and Nomenclature

CI - substituent

6 5 4 3 2 1 2 3 4 5 6

1

Double bond

Alkene start from 2 carbon - ethene

1 2 3 4 5

1 2 3 4 5


5 – chloropent- 4 -ene

Ethene/propene – no numbering needed

3, 5 – dimethylhex-1-ene


2 Ethene CH2CH2 C2H4




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

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


Prefix Stem Suffix

Position and

substituent

Longest carbon

chain

Functional

gp

H CI O ‖ ׀ ׀

H - C – C – C - O


(numbering start here)


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


CH3CH(CH3)CH2CH(CH3)CHO

CH3 branch

3 - methylbutanal

2 - ethylpentanal

2-ethyl- 4-methylpentanal

1 2

2 3 4 5 1

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


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

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


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


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


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

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


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


Alcohol and Nomenclature

CI - substituent

1 2 3 4 5 2 3 4

1 Double bond

5 4 3 2 1

5– chloropentan-1-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







OH – functional gp, not alkene

2- methylpropan-2-ol


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


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



CI - substituent

6 5 4 3 2 1 2 3 4 5 6

1

Double bond

5 4 3 2 1



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








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



Prefix Stem Suffix

Position and

substituent Longest carbon

chain

Functional

gp

C1 – functional gp (numbering start here)


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


CH3CH(CH3)CH2CH(CH3)COOH

CH3 branch

3-methylbutanoic acid

2 -ethylpentanoic acid

2-ethyl-4-methylpentanoic acid

1 2

2 3 4 5 1 1 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 2 1


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






3 2 1

H H O

‖ ׀ ׀

HO - C – C – C – OH

׀ ׀

H H

H CI O ‖ ׀ ׀

H - C – C – C - OH

׀ ׀ H H

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



Prefix Stem Suffix

Position and

substituent Longest carbon

chain

Functional

gp

H CI O ‖ ׀ ׀

H - C – C – C - OH


(numbering start here)


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


CH3CH(CH3)CH2CH(CH3)COOH

CH3 branch

2, 3 -dimethylbutanoic acid

5 – hydroxypentanoic acid

2-ethyl- 4-methylpentanoic acid

1 2

2 3 4 5 1 1 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


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)

H H O

‖ ׀ ׀

HO - C – C – C – OH

׀ ׀

H H

(1, 4 butanedioic acid)

3 2 1







3 2 1

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


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


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

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


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


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

http://www.ivyroses.com/Chemistry/Organic/Naming-Ethers.php

http://www.ivyroses.com/Chemistry/Organic/Naming-Ethers.php

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


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


Halogenoalkane and Nomenclature

CI - halogen

5 4 3 2 1 2 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


1 chloromethane CH3CI CH3CI

2 chloroethane CH3CH2CI C2H5CI

3 chloropropane CH3CH2CH2CI C3H7CI

4 chlorobutane CH3(CH2)2CH2CI C4H9CI

5 chloropentane CH3(CH2)3CH2CI C5H11CI

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

3 4 8 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

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


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

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


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

3 4 8 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

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


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

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

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


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

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

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