Transcript Slide 1

Functional Groups in Organic Compounds
(workshop)
University of Lincoln
presentation
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CLASSIFICATION OF
HYDROCARBON COMPOUNDS
HYDROCARBONS
contain only C and H atoms
AROMATIC
Hydrocarbons must contain a
BENZENE ring
ALIPHATIC
hydrocarbons
SATURATED
hydrocarbons
contain C–C and C–H
single bonds only (ALKANES)
UNSATURATED
hydrocarbons
contain at least 1 C–C multiple bond
ALKENE
contains the
C=C functional group
ALKYNE
contains the
C≡C functional group
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FUNCTIONAL GROUPS
Name of functional
group
Functional group
Alcohol
R
Aldehyde
R
Example
Endings on names
Ethanol
-ol
Ethanal (acetaldehyde)
-al
Propanone (acetone)
-one
Ethanoic acid (acetic acid)
-oic acid
Ethyl ethanoate (ethyl
acetate)
-oate
R
Diethyl ether
Ether
NH2
Ethylamine
-amine
Ethanamide (Acetamide)
-amide
Bromoethane
Halo-
Ethanoyl chloride
-oyl chloride
Ethanenitrile
-nitrile
OH
O
H
O
Ketone
R≠H
R
R
O
Carboxylic acid
R
OH
O
Ester
R = alkyl
R
O R
Ether
R O
Amine
R
Amide
R
O
NH2
Halogenoalkane
R
Acid chloride
R
X = F, Cl, Br, I
X
O
Cl
Nitrile
R
Nitro
R
NO2
Nitromethane
Nitro-
Thiol
R
SH
Ethanethiol
-thiol
N
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FUNCTIONAL GROUPS
Name of functional
group
Alcohol
Functional group
R
Example
Endings on names
Ethanol
-ol
Ethanal (acetaldehyde)
-al
Propanone (acetone)
-one
Ethanoic acid (acetic acid)
-oic acid
Ethyl ethanoate (ethyl
acetate)
-oate
R
Diethyl ether
Ether
NH2
Ethylamine
-amine
Ethanamide (Acetamide)
-amide
OH
O
Aldehyde
R
H
O
Ketone
R≠H
R
R
O
Carboxylic acid
R
O
R = alkyl
R
O R
Ether
R O
Amine
R
Amide
R
O
NH2
Halogenoalkane
R
Acid chloride
R
X = F, Cl, Br, I
X
O
Bromoethane
R–CH2OH
SECONDARY (2y)
ALCOHOL
OH
Ester
PRIMARY (1y)
ALCOHOL
R2–CHOH
TERTIARY (3y)
ALCOHOL
R3–COH
Where R– is any alkyl
Halogroup
Ethanoyl chloride
-oyl chloride
Ethanenitrile
-nitrile
Cl
Nitrile
R
Nitro
R
NO2
Nitromethane
Nitro-
Thiol
R
SH
Ethanethiol
-thiol
N
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FUNCTIONAL GROUPS
Name of functional
group
Functional group
Alcohol
R
Aldehyde
R
Ketone
Example
Endings on names
Ethanol
-ol
Ethanal (acetaldehyde)
-al
Propanone (acetone)
-one
Ethanoic acid (acetic acid)
-oic acid
Ethyl ethanoate (ethyl
acetate)
-oate
R
Diethyl ether
Ether
NH2
Ethylamine
-amine
Ethanamide (Acetamide)
-amide
Bromoethane
Halo-
Ethanoyl chloride
-oyl chloride
Ethanenitrile
-nitrile
OH
O
H
O
R≠H
R
R
Carboxylic acid
O
R
OH
Ester
O
R = alkyl
R
O R
Ether
R O
Amine
R
Amide
R
O
An acid is a
proton (H+)
donor
NH2
Halogenoalkane
R
Acid chloride
R
X = F, Cl, Br, I
X
O
Cl
Nitrile
R
Nitro
R
NO2
Nitromethane
Nitro-
Thiol
R
SH
Ethanethiol
-thiol
N
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FUNCTIONAL GROUPS
Name of functional
group
Alcohol
Aldehyde
Ketone
Functional group
R
OH
O
R
H
O
R≠H
R
Example
Endings on names
Ethanol
-ol
Ethanal (acetaldehyde)
-al
Propanone (acetone)
-one
R
Carboxylic acid
O
Ethanoic acid (acetic acid)
R
PRIMARY (1y) AMINE
R–NH2
SECONDARY (2y)
AMINE
-oic acid
OH
Ester
O
R = alkyl
R
O R
Ether
Amine
Amide
R
R O
R
NH2
O
R
Ethyl ethanoate (ethyl
acetate)
-oate
Diethyl ether
Ether
Ethylamine
-amine
R2–NH
TERTIARY (3y) AMINE
R3–N
Ethanamide (Acetamide)
Where R– is any alkyl
group
-amide
Bromoethane
Halo-
Ethanoyl chloride
-oyl chloride
Ethanenitrile
-nitrile
NH2
Halogenoalkane
R
Acid chloride
R
X = F, Cl, Br, I
X
O
Cl
Nitrile
R
Nitro
R
NO2
Nitromethane
Nitro-
Thiol
R
SH
Ethanethiol
-thiol
N
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Remember!
GROUP
14
15
16
17
Carbon needs FOUR bonds
Nitrogen needs THREE bonds
Oxygen needs TWO bonds
Fluorine needs ONE bond
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Remember!
By convention…
H
=
H
H
H
H
=
H
H
H
H
H
H
H
H
H
H
H
OH
=
H
H
H
H
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RECOGNISING FUNCTIONAL
GROUPS
HO
CH3
H3C
CH3
Smelling of roses…
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1y ALCOHOL
(–CH2OH)
HO
CH3
H3C
CH3
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1y ALCOHOL
(–CH2OH)
HO
CH3
H3C
CH3
ALKENE
(–C=C–)
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Flower Scent – Freesia
H3C
CH3
CH3
O
CH3
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Ketone (R–COR’)
H3C
CH3
CH3
O
CH3
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Ketone (R–COR’)
H3C
CH3
CH3
O
CH3
Conjugated diene
(–C=C–C=C–)
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Pheromones – Honey bee
Pheromones are
chemicals that
carry messages
O
O
H3C
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OH
O
H3C
O
OH
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O
H3C
O
OH
KETONE
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O
O
H3C
OH
Alkene
Ketone
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Carboxylic Acid
(RCOOH)
O
O
H3C
OH
Alkene
Ketone
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AMPHETAMINES
CH3
NH2
AMPHETAMINE
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AMPHETAMINES
1y AMINE
(RNH2)
CH3
NH2
AMPHETAMINE
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AMPHETAMINES
1y AMINE
(RNH2)
CH3
NH2
AROMATIC RING
(Benzene)
AMPHETAMINE
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AMPHETAMINES
CH3
HN
CH3
METHYLAMPHETAMINE
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AMPHETAMINES
CH3
HN
CH3
1H has been
replaced with a
–CH3 (methyl)
METHYLAMPHETAMINE
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AMPHETAMINES
CH3
HN
CH3
1H has been
replaced with a
–CH3 (methyl)
2y AMINE (RR’NH)
METHYLAMPHETAMINE
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AMPHETAMINES
AROMATIC RING
(Benzene)
CH3
HN
CH3
1H has been
replaced with a
–CH3 (methyl)
2y AMINE (RR’NH)
METHYLAMPHETAMINE
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ASPIRIN
O
OH
O
O
CH3
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ASPIRIN
O
CARBOXYLIC ACID
(RCOOH)
OH
O
O
CH3
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ASPIRIN
O
CARBOXYLIC ACID
(RCOOH)
OH
O
O
CH3
ESTER (RCOOR’)
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ASPIRIN
O
CARBOXYLIC ACID
(RCOOH)
OH
O
O
CH3
AROMATIC RING
(Benzene)
ESTER (RCOOR’)
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Bullet-proof vests and spider silk
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KEVLAR (a polyamide)
NH
NH
CH3
H3C
O
O
n
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KEVLAR
NH
NH
CH3
H3C
O
O
n
AMIDE
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KEVLAR
AROMATIC
RINGS
NH
NH
CH3
H3C
O
O
n
AMIDE
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Cat Nap (Octadec-9-eneamide)
CH3
H2N
O
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Cat Nap (Octadec-9-eneamide)
ALKENE
CH3
H2N
O
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Cat Nap (Octadec-9-eneamide)
ALKENE
AMIDE
CH3
H2N
O
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CANNABIS
CH3
OH
H3C
H3C
O
C5H11
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CANNABIS
CH3
OH
H3C
H3C
O
C5H11
AROMATIC RING
(Benzene)
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CANNABIS
CH3
OH
H3C
H3C
O
AROMATIC
ALCOHOL – A
PHENOLIC
GROUP
C5H11
AROMATIC RING
(Benzene)
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CANNABIS
CH3
ALKENE
OH
H3C
H3C
O
AROMATIC
ALCOHOL – A
PHENOLIC
GROUP
C5H11
AROMATIC RING
(Benzene)
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CANNABIS
CH3
ALKENE
OH
H3C
H3C
CYCLIC ETHER
O
AROMATIC
ALCOHOL – A
PHENOLIC
GROUP
C5H11
AROMATIC RING
(Benzene)
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LSD (lysergic acid diethylamide)
H3C
H
N
CON(C2H5)2
HN
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LSD
O
CH3
N
CH3
H3C
N
N
H
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LSD
O
CH3
N
CH3
H3C
N
DIETHYLAMIDE
N
H
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LSD
O
CH3
N
3Y AMINE
CH3
H3C
N
DIETHYLAMIDE
N
H
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LSD
O
CH3
N
3Y AMINE
CH3
H3C
N
DIETHYLAMIDE
2Y AMINE
N
H
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LSD
O
CH3
N
3Y AMINE
CH3
H3C
N
DIETHYLAMIDE
ALKENES
2Y AMINE
N
H
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LSD
O
CH3
N
3Y AMINE
CH3
H3C
N
DIETHYLAMIDE
CONJUGATED
DIENE
ALKENES
2Y AMINE
N
H
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Identify FOUR functional groups
in cocaine
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COCAINE
H
N
O
O
O
O
CH3
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COCAINE
H
N
O
O
O
O
2 ESTERS
CH3
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COCAINE
H
N
2y AMINE
O
O
O
O
2 ESTERS
CH3
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COCAINE
AROMATIC
H
N
2y AMINE
O
O
O
O
2 ESTERS
CH3
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Opium
Morphine
Codeine
Thebaine
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OPIUM
O
H3C
HO
O
O
N
HO
CH3
CH3
CODEINE
MORPHINE
H3C
N
HO
O
O
O
H3C
O
O
H3C
O
N
CH3
H3C
O
N
O
THEBAINE
CH3
HEROIN
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Identify the functional groups in
morphine
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MORPHINE
HO
O
HO
N
CH3
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MORPHINE
HO
O
ALCOHOL
HO
N
CH3
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MORPHINE
PHENOL
HO
O
ALCOHOL
HO
N
CH3
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MORPHINE
PHENOL
CYCLIC
ETHER
ALCOHOL
HO
O
HO
N
CH3
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MORPHINE
PHENOL
CYCLIC
ETHER
ALCOHOL
AROMATIC
HO
O
HO
N
CH3
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MORPHINE
PHENOL
CYCLIC
ETHER
ALCOHOL
AROMATIC
HO
O
HO
3Y AMINE
N
CH3
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MORPHINE
PHENOL
CYCLIC
ETHER
ALCOHOL
AROMATIC
HO
O
HO
3Y AMINE
N
CH3
ALKENE
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What’s the difference between
morphine and codeine?
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HO
H3C
O
HO
O
O
N
CH3
MORPHINE
HO
N
CH3
CODEINE
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PHENOL
HO
H3C
O
HO
O
O
N
CH3
MORPHINE
HO
N
CH3
CODEINE
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PHENOL
ETHER
HO
H3C
O
HO
O
O
N
CH3
MORPHINE
HO
N
CH3
CODEINE
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H3C
H3C
O
O
O
O
N
HO
CH3
CODEINE
H3C
O
N
CH3
THEBAINE
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H3C
H3C
O
O
O
O
N
HO
CH3
CODEINE
H3C
O
N
CH3
THEBAINE
ALCOHOL
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H3C
H3C
O
O
O
N
HO
CH3
H3C
CODEINE
ALCOHOL
O
O
N
CH3
THEBAINE
ETHER
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HEROIN
O
O
H3C
O
H3C
O
O
N
CH3
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HEROIN
O
O
H3C
2 ESTERS
O
H3C
O
O
N
CH3
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Identify the functional groups in
the ‘magic mushroom’ alkaloids
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MAGIC MUSHROOMS
O
O
HO
P
HO
OH
N
H
P
OH
N
N
H
CH3
H3C
HN
CH3
OH
N
H
N
H3C
CH3
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Acknowledgements
•
•
•
•
•
•
•
JISC
HEA
Centre for Educational Research and Development
School of natural and applied sciences
School of Journalism
SirenFM
http://tango.freedesktop.org
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