functional groups in organic compounds (workshop)

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Functional Groups in Organic Compounds (workshop)

University of Lincoln presentation

http://creativecommons.org/licenses/by-nc-sa/2.0/uk/

http://chemistryfm.blogs.lincoln.ac.uk/


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






Alcohol Ethanol -ol




-oic acid


-oate




-amide






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






Alcohol Ethanol -ol




-oic acid


-oate




-amide






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






Alcohol Ethanol -ol




-oic acid


-oate




-amide






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




Remember!

GROUP

14 Carbon needs FOUR bonds

15 Nitrogen needs THREE bonds

16 Oxygen needs TWO bonds

17 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 – Freesia

CH3CH3

O

CH3

CH3




Ketone (R–COR’)

CH3CH3

O

CH3

CH3




Conjugated diene

(–C=C–C=C–)

Ketone (R–COR’)

CH3CH3

O

CH3

CH3




Pheromones – Honey bee

Pheromones are chemicals

that carry messages

CH3 OH

OO




CH3 OH

OO




KETONE

CH3 OH

OO




Alkene

Ketone

CH3 OH

OO




Carboxylic Acid (RCOOH)

Alkene

Ketone

CH3 OH

OO




AMPHETAMINES

AMPHETAMINE

CH3

NH2



CH3

NH2


AMPHETAMINES1y AMINE (RNH2)

AMPHETAMINE



CH3

NH2


AMPHETAMINES

AROMATIC RING (Benzene)

1y AMINE (RNH2)

AMPHETAMINE




AMPHETAMINES

METHYLAMPHETAMINE

CH3

NHCH3



CH3

NHCH3


AMPHETAMINES

1H has been replaced with a –CH3 (methyl)

METHYLAMPHETAMINE



CH3

NHCH3


AMPHETAMINES

2y AMINE (RR’NH)


METHYLAMPHETAMINE



CH3

NHCH3


AMPHETAMINESAROMATIC

RING (Benzene)

2y AMINE (RR’NH)


METHYLAMPHETAMINE




ASPIRIN

O

CH3

O

O OH



O

CH3

O

O OH


CARBOXYLIC ACID (RCOOH)

ASPIRIN



O

CH3

O

O OH


ESTER (RCOOR’)

ASPIRINCARBOXYLIC

ACID (RCOOH)



O

CH3

O

O OH



ASPIRIN

ESTER (RCOOR’)

CARBOXYLIC ACID (RCOOH)




Bullet-proof vests and spider silk




KEVLAR (a polyamide)

NHCH3

NH

O O

CH3

n



NHCH3

NH

O O

CH3

n


AMIDE

KEVLAR



NHCH3

NH

O O

CH3

n


AROMATIC RINGS

KEVLAR

AMIDE




Cat Nap (Octadec-9-eneamide)

NH2

CH3

O



NH2

CH3

O



ALKENE



NH2

CH3

O



ALKENEAMID

E




CANNABIS

OCH3

CH3

OH

CH3

C5H11



OCH3

CH3

OH

CH3

C5H11


CANNABIS




OCH3

CH3

OH

CH3

C5H11


CANNABIS


AROMATIC ALCOHOL – A PHENOLIC GROUP



OCH3

CH3

OH

CH3

C5H11


CANNABIS



ALKENE



OCH3

CH3

OH

CH3

C5H11


CANNABIS

CYCLIC ETHERAROMATIC

RING (Benzene)


ALKENE




LSD (lysergic acid diethylamide)

N

NH

CON(C2H5)2

CH3

H




LSD

N

NH

CH3

N

CH3

CH3O



N

NH

CH3

N

CH3

CH3O


LSD

DIETHYLAMIDE



N

NH

CH3

N

CH3

CH3O


LSD

3Y AMINE

DIETHYLAMIDE




LSD

3Y AMINE

DIETHYLAMIDE

2Y AMINE

N

NH

CH3

N

CH3

CH3O



N

NH

CH3

N

CH3

CH3O

3Y AMINE

DIETHYLAMIDE

2Y AMINE


LSD

ALKENES



N

NH

CH3

N

CH3

CH3O

3Y AMINE

DIETHYLAMIDE

2Y AMINE

ALKENES


LSD

CONJUGATED DIENE




Identify FOUR functional groups in cocaine




COCAINE

NH

OO

CH3

O

O



NH

OO

CH3

O

O


COCAINE

2 ESTERS



NH

OO

CH3

O

O

2 ESTERS


COCAINE

2y AMINE



NH

OO

CH3

O

O

2 ESTERS

2y AMINE


COCAINEAROMATI

C




Opium

MorphineCodeineThebaine




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




Identify the functional groups in morphine




MORPHINE

OH

OH

O

N

CH3



OH

OH

O

N

CH3


MORPHINE

ALCOHOL



OH

OH

O

N

CH3


MORPHINE

PHENOL

ALCOHOL



OH

OH

O

N

CH3


MORPHINE

CYCLIC ETHER

PHENOL

ALCOHOL



OH

OH

O

N

CH3

CYCLIC ETHER

PHENOL

ALCOHOL


MORPHINEAROMATIC



CYCLIC ETHER

PHENOL

ALCOHOL

OH

OH

O

N

CH3

AROMATIC


MORPHINE

3Y AMINE




MORPHINE

ALKENE

CYCLIC ETHER

PHENOL

ALCOHOL

OH

OH

O

N

CH3

AROMATIC

3Y AMINE




What’s the difference between morphine and

codeine?




CODEINEMORPHINE

OH

OH

O

N

CH3

O

OH

O

N

CH3

CH3



CODEINEMORPHINE

OH

OH

O

N

CH3

O

OH

O

N

CH3

CH3


PHENOL




CODEINEMORPHINE

OH

OH

O

N

CH3

O

OH

O

N

CH3

CH3

PHENOL

ETHER




CODEINE THEBAINE

O

OH

O

N

CH3

CH3 O

O

O

N

CH3

CH3

CH3




CODEINE THEBAINE

O

OH

O

N

CH3

CH3 O

O

O

N

CH3

CH3

CH3

ALCOHOL




ETHERCODEINE THEBAIN

E

O

OH

O

N

CH3

CH3 O

O

O

N

CH3

CH3

CH3

ALCOHOL




HEROIN

O

O

O

N

CH3

CH3

CH3

O

O



O

O

O

N

CH3

CH3

CH3

O

O


HEROIN

2 ESTERS


Identify the functional groups in the ‘magic mushroom’

alkaloids


MAGIC MUSHROOMS

NH

P

O

OH OH

N

CH3CH3NH

P

O

OH OH

NH

CH3

NH

OH

N

CH3CH3


Acknowledgements

• JISC• HEA• Centre for Educational Research and

Development• School of natural and applied sciences• School of Journalism• SirenFM• http://tango.freedesktop.org

functional groups in organic compounds (workshop)

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