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Compound
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NH4OCN + AgCl
Silver
cyanate
Ammonium
chloride
Ammonium
cyanate
Silver
chloride
(soluble)
(soluble)
(soluble)
(insoluble)
[Ag+][OCN] +
[NH4+][Cl]
"I"Imust
must tell
tellyou
you that
that IIcan
canmake
makeurea
urea
without
withoutthe
theuse
useof
ofkidneys,
kidneys,either
eitherman
man
or
or dog.
dog. Ammonium
Ammonium cyanate
cyanateis
is urea."
urea."
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Isomers?
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Single bond:
Double bond:
Triple bond:
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Single bonds
only.
Diamond
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C60H60
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Intermolecular Forces
(1) Dipole-dipole force
If a bond connects two identical atoms, the bonding electrons
are equally shared between the two atoms, e.g., in H2.
If the two atoms are not identical, the bonding electrons are
not equally shared. They are more concentrated on atoms of:
N, O, F, Cl, Br, I than H, C, and hence partial charges develop
at the two atoms, e.g., in HCl and H3CCl.
These molecules are called polar molecules. The partial
charges result in an attractive force, dipole-dipole force,
between the molecules.
Electron cloud is
shared equally.
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Intermolecular Forces
(2) London force (studied by Fritz London)
At sufficiently low temperature, non-polar gases (e.g., H2, F2)
form liquids, in which the molecules are held by each other.
That means there are attractive forces between the non-polar
molecules of these gases. Fritz London recognized that the
motion of electrons in a molecule can create momentary
uneven distribution of charge, resulting in a momentary polar
molecule.
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Intermolecular Forces
(2) London force (contd)
Remarks:
(2a) London force exists for all molecules and atoms.
(2b) Molecules/
atoms with more
electrons have
larger London
force because the
electrons are held
less firmly and the
electron clouds
are more easily
distorted.
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Intermolecular Forces
(2) London force (contd)
Around us: boiling point of hydrocarbon CxHy
x ~ 1-4
x ~ 5-19
x ~ 20-25
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Gasoline
Wax
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Intermolecular Forces
(3) Hydrogen bonding
It is a special intermolecular force between a
F/O/N atom and a hydrogen atom bonded to
another F/O/N atom, e.g.,
Hydrogen bonding is significantly strong than
dipole-dipole force. In many cases, hydrogen
bonding is even
stronger than
London force of
large molecules.
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17
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Chemical Tests
After doing some chemical tests, Whler found that his product
behaved similarly to urea rather than NH 4OCN, and finally confirmed
that the product, obtained in glassware instead of living organisms,
was urea.
Importance: it was possible to produce organic compounds from
inorganic compounds by chemical means, instead of biological starting
materials and without relying on living organisms. The result
discredited vitalism, the theory that the chemicals of living organisms
are fundamentally different from those of inanimate matter. For this
discovery, Whler is considered by many the father of organic
chemistry.
Practical implication: organic compounds might then be produced in a
large-scale.
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Total Synthesis
Yet, for Whlers reaction, the starting materials might costly. Could
chemists go further to use cheap (or even free) starting materials to
obtain urea?
Total synthesis in organic chemistry: the complete chemical synthesis
of complex organic molecules from simpler pieces which are
commercially available in bulk quantities, and are often petrochemical
precursors, but sometimes bulk natural products (e.g. sucrose).
Industrial production of urea:
2NH3 + CO2
+ H 2O
NH3: from another well-known industrial process
CO2: from burning of hydrocarbons
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Total Synthesis
Further challenge: the variety of organic molecules relies on
the possibility of carbon chains, which contain different
numbers of C-C bonds and C-H bonds. Note that urea does
not contain these two types of bonds. The next challenge
would therefore be the creations of these two kinds of bonds.
This was achieved by Hermann Kolbe in 1845 on the total
synthesis of acetic acid.
Acetic acid:
containing C-C bonds and C-H bonds
Ancient production of acetic acid:
Sugar (e.g., in rice) ethanol (in wine) acetic acid
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Total Synthesis
Starting material:
carbon & FeS2 (both from mining)
Reagents: Cl2 & H2 (from electrolysis of NaCl solution)
Key steps:
C-C bond formation: decomposition by heating
C-H bond formation: replace Cl atoms with H atoms
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HH
HH
NN
NN
NN
HH
HH
NN
HH
NN
NN
6 NH3 3 CO 2
HH
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Kjeldahl Method
Due to its low cost & high nitrogen content per unit
mass, some dairy farmers cheat by adding melamine to
their milk products to fool the authoritys rather simple
check on protein content. It is also said that they
did so because they believed that melamine
could be converted to protein in the digestive
system of cows.
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3 NH3
cyanuric acid
hydrogen bonds
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Fatal Network
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27
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