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Organic Chemistry - 1105-Notes
Organic Chemistry - 1105-Notes
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+2
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 Type of
carbon compound
atoms
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
Occurs in nature
Can be done
artificially
C2H4 is also major
raw material for
polymers (later)
Alkynes: Triple bonds as well
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
Making isomers
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
super-imposable
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
Benzene: base of many important
compounds
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
and H
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 incohesive forces: O-H bonds
are polar, C-H bonds are not
Functionalized hydrocarbons
Identifying functional groups from
the formula
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