organic chemistry: classification of organic compounds: seminar
DESCRIPTION
Lecture materials for the Introductory Chemistry course for Forensic Scientists, University of Lincoln, UK. See http://forensicchemistry.lincoln.ac.uk/ for more details.TRANSCRIPT
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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
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
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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
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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) ALCOHOL
R2–CHOH
TERTIARY (3y) ALCOHOL
R3–COH
Where R– is any alkyl group
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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
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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) AMINE
R–NH2
SECONDARY (2y) AMINE
R2–NH
TERTIARY (3y) AMINE
R3–N
Where R– is any alkyl group
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Remember!
GROUP
14 Carbon needs FOUR bonds
15 Nitrogen needs THREE bonds
16 Oxygen needs TWO bonds
17 Fluorine needs ONE bond
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Remember!By convention…
H
H
H H
H
H
OH
H
H
H H
H H
H
H
H
H
H
H
H
H
=
=
=
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RECOGNISING FUNCTIONAL GROUPS
Smelling of roses…
OH
CH3
CH3
CH3
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OH
CH3
CH3
CH3
1y ALCOHOL (–CH2OH)
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OH
CH3
CH3
CH3
1y ALCOHOL (–CH2OH)
ALKENE (–C=C–)
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Flower Scent – Freesia
CH3CH3
O
CH3
CH3
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Ketone (R–COR’)
CH3CH3
O
CH3
CH3
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Conjugated diene
(–C=C–C=C–)
Ketone (R–COR’)
CH3CH3
O
CH3
CH3
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Pheromones – Honey bee
Pheromones are chemicals
that carry messages
CH3 OH
OO
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CH3 OH
OO
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KETONE
CH3 OH
OO
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Alkene
Ketone
CH3 OH
OO
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Carboxylic Acid (RCOOH)
Alkene
Ketone
CH3 OH
OO
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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
CH3
O
NH2
CH3
O
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Cat Nap (Octadec-9-eneamide)
ALKENE
NH2
CH3
O
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Cat Nap (Octadec-9-eneamide)
ALKENEAMID
E
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CANNABIS
OCH3
CH3
OH
CH3
C5H11
OCH3
CH3
OH
CH3
C5H11
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CANNABIS
AROMATIC RING (Benzene)
OCH3
CH3
OH
CH3
C5H11
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CANNABIS
AROMATIC RING (Benzene)
AROMATIC ALCOHOL – A PHENOLIC GROUP
OCH3
CH3
OH
CH3
C5H11
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CANNABIS
AROMATIC RING (Benzene)
AROMATIC ALCOHOL – A PHENOLIC GROUP
ALKENE
OCH3
CH3
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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COCAINE
NH
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
THEBAINEHEROIN
O
O
O
N
CH3
CH3
CH3
O
O
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Identify the functional groups in morphine
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MORPHINE
OH
OH
O
N
CH3
OH
OH
O
N
CH3
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MORPHINE
ALCOHOL
OH
OH
O
N
CH3
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MORPHINE
PHENOL
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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HEROIN
O
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
N
CH3CH3NH
P
O
OH OH
NH
CH3
NH
OH
N
CH3CH3
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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