Functional Groups in Organic Compounds (workshop)
University of Sulaimani presentation
CLASSIFICATION OF HYDROCARBON COMPOUNDS
HYDROCARBONS contain only C and H atoms
ALIPHATIC hydrocarbons
AROMATIC Hydrocarbons must contain a
BENZENE ring
UNSATURATED hydrocarbons
contain at least 1 C–C multiple bond
SATURATED hydrocarbons
contain C–C and C–H single bonds only (ALKANES)
ALKENE contains the
C=C functional group
ALKYNE contains the
C≡C functional group
FUNCTIONAL GROUPSName of functional group
Functional group Example Endings on names
Alcohol Ethanol -ol
Aldehyde Ethanal (acetaldehyde) -al
Ketone R≠H Propanone (acetone) -one
Carboxylic acid Ethanoic acid (acetic acid)
-oic acid
Ester R = alkyl Ethyl ethanoate (ethyl acetate)
-oate
Ether Diethyl ether Ether
Amine Ethylamine -amine
Amide Ethanamide (Acetamide)
-amide
Halogenoalkane X = F, Cl, Br, I Bromoethane Halo-
Acid chloride Ethanoyl chloride -oyl chloride
Nitrile Ethanenitrile -nitrile
Nitro Nitromethane Nitro-
Thiol Ethanethiol -thiol
OHR
R
O
H
R
O
R
R
O
OH
R
O
O R
OR
R
NH2R
SHR
NO2R
R N
R
O
Cl
XR
R
O
NH2
FUNCTIONAL GROUPSName of functional group
Functional group Example Endings on names
Alcohol Ethanol -ol
Aldehyde Ethanal (acetaldehyde) -al
Ketone R≠H Propanone (acetone) -one
Carboxylic acid Ethanoic acid (acetic acid)
-oic acid
Ester R = alkyl Ethyl ethanoate (ethyl acetate)
-oate
Ether Diethyl ether Ether
Amine Ethylamine -amine
Amide Ethanamide (Acetamide)
-amide
Halogenoalkane X = F, Cl, Br, I Bromoethane Halo-
Acid chloride Ethanoyl chloride -oyl chloride
Nitrile Ethanenitrile -nitrile
Nitro Nitromethane Nitro-
Thiol Ethanethiol -thiol
OHR
R
O
H
R
O
R
R
O
OH
R
O
O R
OR
R
NH2R
SHR
NO2R
R N
R
O
Cl
XR
R
O
NH2
PRIMARY (1y) ALCOHOL R–CH2OH
SECONDARY (2y) ALCOHOLR2–CHOH
TERTIARY (3y) ALCOHOLR3–COH
Where R– is any alkyl group
FUNCTIONAL GROUPSName of functional group
Functional group Example Endings on names
Alcohol Ethanol -ol
Aldehyde Ethanal (acetaldehyde) -al
Ketone R≠H Propanone (acetone) -one
Carboxylic acid Ethanoic acid (acetic acid)
-oic acid
Ester R = alkyl Ethyl ethanoate (ethyl acetate)
-oate
Ether Diethyl ether Ether
Amine Ethylamine -amine
Amide Ethanamide (Acetamide)
-amide
Halogenoalkane X = F, Cl, Br, I Bromoethane Halo-
Acid chloride Ethanoyl chloride -oyl chloride
Nitrile Ethanenitrile -nitrile
Nitro Nitromethane Nitro-
Thiol Ethanethiol -thiol
OHR
R
O
H
R
O
R
R
O
OH
R
O
O R
OR
R
NH2R
SHR
NO2R
R N
R
O
Cl
XR
R
O
NH2
An acid is a proton (H+)
donor
FUNCTIONAL GROUPSName of functional group
Functional group Example Endings on names
Alcohol Ethanol -ol
Aldehyde Ethanal (acetaldehyde) -al
Ketone R≠H Propanone (acetone) -one
Carboxylic acid Ethanoic acid (acetic acid)
-oic acid
Ester R = alkyl Ethyl ethanoate (ethyl acetate)
-oate
Ether Diethyl ether Ether
Amine Ethylamine -amine
Amide Ethanamide (Acetamide)
-amide
Halogenoalkane X = F, Cl, Br, I Bromoethane Halo-
Acid chloride Ethanoyl chloride -oyl chloride
Nitrile Ethanenitrile -nitrile
Nitro Nitromethane Nitro-
Thiol Ethanethiol -thiol
OHR
R
O
H
R
O
R
R
O
OH
R
O
O R
OR
R
NH2R
SHR
NO2R
R N
R
O
Cl
XR
R
O
NH2
PRIMARY (1y) AMINER–NH2
SECONDARY (2y) AMINER2–NH
TERTIARY (3y) AMINER3–N
Where R– is any alkyl group
Remember!GROUP
14 Carbon needs FOUR bonds15 Nitrogen needs THREE bonds16 Oxygen needs TWO bonds17 Fluorine needs ONE bond
Remember!By convention…
H
H
H H
H
H
OH
H
H
H H
H H
H
H
H
H
H
H
H
H
=
=
=
RECOGNISING FUNCTIONAL GROUPS
Smelling of roses…
OH
CH3
CH3
CH3
OH
CH3
CH3
CH3
1y ALCOHOL (–CH2OH)
OH
CH3
CH3
CH3
1y ALCOHOL (–CH2OH)
ALKENE (–C=C–)
Flower Scent – FreesiaCH3CH3
O
CH3
CH3
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Ketone (R–COR’)
CH3CH3
O
CH3
CH3
Conjugated diene (–C=C–C=C–)
Ketone (R–COR’)
CH3CH3
O
CH3
CH3
Pheromones – Honey beePheromones
are chemicals that carry messages
CH3 OH
OO
CH3 OH
OO
KETONE
CH3 OH
OO
AlkeneKetone
CH3 OH
OO
Carboxylic Acid (RCOOH)
AlkeneKetone
CH3 OH
OO
AMPHETAMINES
AMPHETAMINE
CH3
NH2
CH3
NH2
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AMPHETAMINES1y AMINE (RNH2)
AMPHETAMINE
CH3
NH2
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AMPHETAMINES
AROMATIC RING (Benzene)
1y AMINE (RNH2)
AMPHETAMINE
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AMPHETAMINES
METHYLAMPHETAMINE
CH3
NHCH3
CH3
NHCH3
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AMPHETAMINES
1H has been replaced with a –CH3 (methyl)
METHYLAMPHETAMINE
CH3
NHCH3
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AMPHETAMINES
2y AMINE (RR’NH)
1H has been replaced with a –CH3 (methyl)
METHYLAMPHETAMINE
CH3
NHCH3
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AMPHETAMINESAROMATIC
RING (Benzene)
2y AMINE (RR’NH)
1H has been replaced with a –CH3 (methyl)
METHYLAMPHETAMINE
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ASPIRIN
O
CH3
O
O OH
O
CH3
O
O OH
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CARBOXYLIC ACID (RCOOH)
ASPIRIN
O
CH3
O
O OH
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ESTER (RCOOR’)
ASPIRINCARBOXYLIC
ACID (RCOOH)
O
CH3
O
O OH
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AROMATIC RING (Benzene)
ASPIRIN
ESTER (RCOOR’)
CARBOXYLIC ACID (RCOOH)
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Bullet-proof vests and spider silk
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KEVLAR (a polyamide)
NHCH3
NH
O O
CH3
n
NHCH3
NH
O O
CH3
n
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AMIDE
KEVLAR
NHCH3
NH
O O
CH3
n
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AROMATIC RINGS
KEVLAR
AMIDE
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Cat Nap (Octadec-9-eneamide)
NH2
CH3O
NH2
CH3O
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Cat Nap (Octadec-9-eneamide)
ALKENE
NH2
CH3O
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Cat Nap (Octadec-9-eneamide)
ALKENEAMID
E
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CANNABIS
OCH3CH3
OH
CH3
C5H11
OCH3CH3
OH
CH3
C5H11
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CANNABIS
AROMATIC RING (Benzene)
OCH3CH3
OH
CH3
C5H11
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CANNABIS
AROMATIC RING (Benzene)
AROMATIC ALCOHOL – A PHENOLIC GROUP
OCH3CH3
OH
CH3
C5H11
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CANNABIS
AROMATIC RING (Benzene)
AROMATIC ALCOHOL – A PHENOLIC GROUP
ALKENE
OCH3CH3
OH
CH3
C5H11
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CANNABIS
CYCLIC ETHERAROMATIC
RING (Benzene)
AROMATIC ALCOHOL – A PHENOLIC GROUP
ALKENE
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LSD (lysergic acid diethylamide)
N
NH
CON(C2H5)2
CH3
H
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LSD
N
NH
CH3
N
CH3
CH3O
N
NH
CH3
N
CH3
CH3O
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LSD
DIETHYLAMIDE
N
NH
CH3
N
CH3
CH3O
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LSD
3Y AMINE
DIETHYLAMIDE
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LSD
3Y AMINE
DIETHYLAMIDE
2Y AMINE
N
NH
CH3
N
CH3
CH3O
N
NH
CH3
N
CH3
CH3O
3Y AMINE
DIETHYLAMIDE
2Y AMINE
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LSD
ALKENES
N
NH
CH3
N
CH3
CH3O
3Y AMINE
DIETHYLAMIDE
2Y AMINE
ALKENES
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LSD
CONJUGATED DIENE
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Identify FOUR functional groups in cocaine
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COCAINENH
OO
CH3
O
O
NH
OO
CH3
O
O
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COCAINE
2 ESTERS
NH
OO
CH3
O
O
2 ESTERS
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COCAINE
2y AMINE
NH
OO
CH3
O
O
2 ESTERS
2y AMINE
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COCAINEAROMATI
C
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Opium
MorphineCodeineThebaine
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OPIUMOH
OH
O
N
CH3
O
OH
O
N
CH3
CH3
O
O
O
N
CH3
CH3
CH3
MORPHINE CODEINE
THEBAINE HEROIN
O
O
O
N
CH3
CH3
CH3
O
O
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Identify the functional groups in morphine
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MORPHINEOH
OH
O
N
CH3
OH
OH
O
N
CH3
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MORPHINE
ALCOHOL
OH
OH
O
N
CH3
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MORPHINEPHENOL
ALCOHOL
OH
OH
O
N
CH3
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MORPHINE
CYCLIC ETHER
PHENOL
ALCOHOL
OH
OH
O
N
CH3
CYCLIC ETHER
PHENOL
ALCOHOL
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MORPHINEAROMATIC
CYCLIC ETHER
PHENOL
ALCOHOL
OH
OH
O
N
CH3
AROMATIC
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MORPHINE
3Y AMINE
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MORPHINE
ALKENE
CYCLIC ETHER
PHENOL
ALCOHOL
OH
OH
O
N
CH3
AROMATIC
3Y AMINE
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What’s the difference between morphine and
codeine?
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CODEINEMORPHINE
OH
OH
O
N
CH3
O
OH
O
N
CH3
CH3
CODEINEMORPHINE
OH
OH
O
N
CH3
O
OH
O
N
CH3
CH3
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PHENOL
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CODEINEMORPHINE
OH
OH
O
N
CH3
O
OH
O
N
CH3
CH3
PHENOL
ETHER
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CODEINE THEBAINE
O
OH
O
N
CH3
CH3 O
O
O
N
CH3
CH3
CH3
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CODEINE THEBAINE
O
OH
O
N
CH3
CH3 O
O
O
N
CH3
CH3
CH3
ALCOHOL
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ETHERCODEINE THEBAIN
E
O
OH
O
N
CH3
CH3 O
O
O
N
CH3
CH3
CH3
ALCOHOL
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HEROINO
O
O
N
CH3
CH3
CH3
O
O
O
O
O
N
CH3
CH3
CH3
O
O
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HEROIN
2 ESTERS
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Identify the functional groups in the ‘magic mushroom’
alkaloids
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MAGIC MUSHROOMS
NH
P
O
OH OH
NCH3CH3
NH
P
O
OH OH
NHCH3
NH
OH
NCH3CH3
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Acknowledgements• JISC• HEA• Centre for Educational Research and
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