Functional groups
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Transcript Functional groups
Organic Chemistry
The unique chemistry
of carbon
Learning objectives
Describe two reasons for abundance of carbon
compounds
Distinguish between inorganic and organic
carbon and other compounds
Distinguish between isomers and non-isomers
Describe differences between optical and
geometric isomerism
Distinguish between aromatic and nonaromatic
Identify common functional groups
One element – one branch of
chemistry
Organic compounds based on
carbon: 13 million and rising (fast)
100,000 new
compounds synthesized
annually
All 91 other elements combined:
only 300,000 compounds
Factoids about carbon
Fairly abundant in earth’s crust – but
not enough to explain domination
Highly significant to life
Key element in the human organism –
and all others
“God’s goof”:
The absence of stable mass 5
C and O are abundant because the atom with
mass 5 is unstable
Otherwise atom building after the Big Bang
would have resulted in much heavier elements
The thoughts of a cosmological atheist Fred
Hoyle:
“Some supercalculating intellect must have designed the
properties of the carbon atom, otherwise the chance of my
finding such an atom through the blind forces of nature
would be utterly minuscule….The numbers one calculates
from the facts seem to me so overwhelming as to put this
conclusion almost beyond question”
Organic and inorganic carbon
Inorganic carbon: ionic compounds
where carbon is incorporated as
carbonate – CO32Organic carbon: compounds of
carbon with itself, hydrogen and
other elements – by far the most
important
Organic carbon forms a thin canopy
Unique (?) conditions on earth that
support life
Earth’s
surface organic
Earth’s
crust inorganic
Vitalism and organic chemistry
Inorganic compounds were salts of the earth
Stable and easily synthesized
Organic compounds were of living organisms
Fragile and not easily synthesized
Belief in Vitalism posited that only living
organisms possessed a vital force necessary to
create organic compounds
In 1828 urea was synthesized and vitalism was
on the way out
Seven ages of man - many ages of a
carbon atom
Combustion: C + O2 CO2
Neutralization by seawater: CO2 + Ca(OH)2 CaCO3 + H2O
Reaction with acid rain: CaCO3 + H2SO4 CO2
Photosynthesis: CO2 Organic compounds (OC)
Vegetation decomposes: OC fossil fuels (FF)
Vegetation consumed by animal: OC new compounds
(proteins, DNA etc.)
Respiration: sugars CO2 + energy
Industrialization: FF C, CO2 + energy
Manufacturing: FF Plastics, polymers, drugs etc.
Waste disposal Fossil fuels, CO2
Two reasons why carbon is unique
Carbon can form four bonds – four
valence electrons
Carbon forms very strong bonds with
itself – chains, rings etc.
Classifying organic compounds
Hydrocarbons are the simplest
organic compounds
Contain only C and H
Simplest is CH4 (natural gas)
Intermediate C8H18 (petroleum)
Synthetic polymers contain
thousands of atoms
Alkanes
All bonds are single
Saturated
No new bonds can be added
General formula CnH2n+1
Summary of types
Representing molecules
Molecular formula
Shows atoms in the molecule
Structural formula
Shows how they are all connected
Condensed structural formula
Simplified representation of connections
Naming organic compounds
Meth - ane
Number of
carbon
atoms
Type of
compound
Numbers game: count the carbon
atoms in the chain
Saturation bonding:
Multiple bonds and unsaturation
Saturated: no more bonds can be added
Unsaturated: more bonds can be formed
More reactive compounds
Alkenes contain double bonds
Going bananas:
Ethylene and fruit ripening
Examples of alkynes
Isomerism
Same number and type of atoms
Different arrangements
Hydrocarbons can have straight and branched
chains
Isomers simplified
Alkane isomers
General formula
CnH2n+1
Three isomers of pentane
C5H12
Five isomers of hexane
C6H14
Number of isomers mushrooms as
chain length increases
CH4 – 1 possibility
C2H6 – 1
C3H8 – 1
C4H10 – 2
C5H12 – 3
C8H18 – 18
C10H22 – 75
C20H42 – 366,319
Optical isomerism is a special
variation
Molecules exhibit handedness –
mirror images which are not superimposable
Must have tetrahedral carbon with
four different groups attached
This carbon is chiral
Isomers and reaction yield
Each chiral carbon produces two
isomers
If there are n chiral carbon atoms
there are 2n isomers
Optical isomers are important in
nature
Amino acids are building blocks of
proteins
Amino acids are chiral
Proteins contain hundreds –
thousands of amino acids
Getting the correct isomer is a big
deal
Geometric isomers:
Isomerism and a healthy diet
What’s with all this trans fats anyway?
Ask a Chicago Alderman
Different geometry - same attachments
Cis isomers:
Don’t pack together
Cis isomers have low viscosity - good
Trans isomers:
Pack together tightly
Trans isomers are solids - bad
Aromatic: the stuff of dreams
Benzene ring contains 6 C atoms
Bonding is resonant – more stable
than expected
All aromatic compounds contain at
least one benzene ring
Benzene, C6H6, is one of the most
important industrial chemicals
Toxicity of benzene
Benzene is regarded as a highly
carcinogenic substance
Use and disposal of benzene are
regulated
Compounds containing benzene
rings are not necessarily toxic
Functional groups
Chemistry of organic compounds is
determined by functional groups
Functional group is an atom or group
of atoms that are different from C
Heteroatoms confer very different
properties on the substance
Heteroatoms affect physical and
chemical properties
C2H6 (ethane) is a gas at RT
C2H6 is insoluble in water
C2H6O (ethanol) is a liquid at RT
C2H6O is soluble in water
Differences
in cohesive forces: O-H bonds
are polar, C-H bonds are not
Functionalized hydrocarbons
Chlorocarbons and the environment
Important uses – important problems
Solvents CH2Cl2
Insecticides
DDT
Refrigerants CFCs
Alcohols: hic
Functional group –OH
Polar molecules dissolve in H2O
Ethanol: good for your health/bad
for your health?
Smoke gets in my eyes: olefactory
pleasures of aldehydes
C=O is carbonyl group
Aldehyde contains RCHO
Formaldehyde is a preservative and a
product of burning wood
Acrolein is a product of barbequing
Common smells and flavours
Ketones
Ketone is R1R2CO
Acetone is a common solvent
Smell found in cinnamon
Raspberries
Carboxylic acids
Commonly found in citrus fruits and
any sour foods
Formic acid present in ant and bee
stings
Esters: sweet aromas and flavours
Ester group is R1COOR2
Sweet aroma in pineapples, jasmine
Synthetic versions are very common
Ethers
Ethers contain R1-O-R2
No -OH bonds
Not soluble in water
Anesthetics
Amines: the stench of death
Amines contain NR1R2R3
Rotting fish
Decaying flesh
Illicit drugs