IB Chemistry on Homologous series and functional groups of organic molecules

13
Class Functional group/name Suffix Examples Formula alkane C - C ane ethane C n H 2n+2 alkene C = C Alkenyl ene ethene C n H 2n alkyne C ≡ C Alkynyl yne ethyne C n H 2n-2 alcohol O-H Hydroxyl ol ethanol C n H 2n+1 OH ether C – O - C Ether oxyalkane methoxymethane R –O -R ketone O C – C - C Carbonyl one propanone C n H 2n O or R-CO-R aldehyde C = O ׀H Aldehyde anal ethanal C n H 2n O or R -CHO Carboxylic acid O C – O H Carboxyl oic acid ethanoic acid C n H 2n+1 COOH ester O C – O –C Ester oate ethyl ethanoate R – COO-R amide CONH 2 Amide anamide propanamide amine NH 2 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 Click here download Rasmol Click here download PyMol Click here download ACD Lab Click here download Jmol 3 2 1

Transcript of IB Chemistry on Homologous series and functional groups of organic molecules

Page 1: IB Chemistry on Homologous series and functional groups of organic molecules

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

Click here download Rasmol Click here download PyMol Click here download ACD Lab Click here download Jmol

3 2 1

Page 2: IB Chemistry on Homologous series and functional groups of organic molecules

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 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

Page 3: IB Chemistry on Homologous series and functional groups of organic molecules

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 2 CH3 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 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

Page 4: IB Chemistry on Homologous series and functional groups of organic molecules

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

Click here organic notes Click here e text organic

Click here chemical search.

Page 5: IB Chemistry on Homologous series and functional groups of organic molecules

• 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

Page 6: IB Chemistry on Homologous series and functional groups of organic molecules

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

Page 7: IB Chemistry on Homologous series and functional groups of organic molecules

• 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 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

Display full SF Condensed SF Ball /stick model Spacefilling

H H H

׀ ׀ ׀

C = C – C - H

׀ ׀

H H

CH2=CHCH3

Page 8: IB Chemistry on Homologous series and functional groups of organic molecules

• 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

Ball /stick model Spacefilling Condensed SF Display full SF

H

׀

H - C ≡ C – C – H

׀

H

CH≡C-CH3

propyne

Structural formula – arrangement atoms in molecule

Display full SF Condensed SF Ball /stick model Spacefilling

H H

׀ ׀

H - C – C – OH

׀ ׀

H H

CH3CH2OH

ethanol

Page 9: IB Chemistry on Homologous series and functional groups of organic molecules

• 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 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

Page 10: IB Chemistry on Homologous series and functional groups of organic molecules

• 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

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

Display full SF Condensed SF Ball /stick model Spacefilling

O H

׀ ‖

H - C – O – C - H

׀

H

HCOOCH3

Methyl methanoate

Page 11: IB Chemistry on Homologous series and functional groups of organic molecules

• 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

Hydrocarbon skeleton Functional gp

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methanamine

H H

׀ ׀

H - C – N - H

׀

H

CH3NH2

Hydrocarbon skeleton Functional gp

Structural formula – arrangement atoms in molecule

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methanamide

O H

׀ ‖

H - C – N - H

HCONH2

Page 12: IB Chemistry on Homologous series and functional groups of organic molecules

• 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

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

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

Page 13: IB Chemistry on Homologous series and functional groups of organic molecules

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

Ball /stick model Spacefilling Condensed SF Display full SF

CH3CI

chloromethane

Structural formula – arrangement atoms in molecule

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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