Organic Chemistry
What is Organic chemistry?
• Historical
– “Organic” – derived from living organisms
– Compounds such as sugar, urea, starch
– Vitalism: natural products needed a “VitalForce” to
create them
– Wöhler (1828) synthesis of urea
Inorganic
Organic
Organic Chemistry Today
Organic Chemistry:
The study of compounds and reactions involving carbon,
regardless of source (Kekulé, 1861)
Organic Chemistry: The chemistry of carbon
and carbon-based compounds
Why should we care?
– Biochemistry
– Pharmaceuticals
– Industry
• Polymers
• Explosives
OH
O
OH
O
O
Acetyl Salicylic acid
n
*
*
Polypropylene
O
CH3
+
O
O
+
N
N
O
+
O
N
O
2,4,6-Trinitrotoluene
Organic Chemistry in everyday life:
Smells & tastes: fruits, chocolate, fish, mint
Medications: Aspirin, Tylenol, Decongestants, Sedatives
Addictive substances: Caffeine, Nicotine, Alcohol,
Narcotics
Hormones/Neurotransmitters: Adrenaline, Epinephrine
Food/Nutrients: Carbohydrates, Protein, Fat, Vitamins
Genetics: DNA, RNA
Consumer products: Plastics, Nylon, Rayon, Polyester
Organic Molecules
the brain
dopamine
Synaptic neurotransmission
Dopamine neuron
terminal
Target Neurons
dendrite
axon
cell body
dopamine
transporter
vesicles
tyrosine
l-dopa
dopamine
postsynaptic
receptor
presynaptic
receptor
synapse
Dopamine
a neurotransmitter
present in the brain
a space filling model
Dopamine
a neurotransmitter
present in the brain
hydrogen
oxygen
nitrogen
carbon
a ball and stick model
Dopamine
H
O
H
C
H H H
C
N
C
C
C
H
C
C H H
O
C
H
H
H
Dopamine. Dash Molecular
formula
two lines = 4
electrons
H
O
H
C
H H H
C
N
C
C
C
H
C
C H H
O
C
H
H
H
one line =
electrons
Condensed molecular formula =
2
C8H11NO2
Dopamine. Line-Angle Molecular
formula
H
HO
O
H
C
H H H
NH
C
N 2
C
C
C
H
C
C H H
HO
O
C
H
H
H
all nodes are carbon
add hydrogens until there are 4
bonds to each carbon atom
H
O
H H H
C
N
C
C
C
H
C
C H H
O
C
H
H
H
HO
H
C
NH2
HO
Both structures represent the
molecule dopamine but the bottom
structure is simpler to draw.
H
O
H H H
C
N
C
C
C
H
C
C H H
O
C
H
H
H
HO
HO
Link->
H
C
NH2
Chemical Formulae
• Empirical formula
– Smallest integer ratio between atoms of
different types in a molecule.
• Molecular formula
– Actual number of atoms of each type in a
molecule.
• Example:
– Ethene (C2H4) and cyclohexane (C6H12) both
have the empirical formula (CH2)
Ibuprofen is the active ingredient in a number
of analgesics. The structure of ibuprofen is
given below. What is the molecular formula of
ibuprofen?
C H O2
HO
O
ibuprofen
Ibuprofen is the active ingredient in a number
of analgesics. The structure of ibuprofen is
given below. What is the molecular formula of
ibuprofen?
C13H O2
HO
C
O
C
C
C
C
C
C
C
C
ibuprofen
C
C
C
C
Ibuprofen is the active ingredient in a number
of analgesics. The structure of ibuprofen is
given below. What is the molecular formula of
ibuprofen?
C13H O2
H
H C H
HO
C
C
C
C
C
C
H
O
C
C
C
C
C
C
ibuprofen
Ibuprofen is the active ingredient in a number
of analgesics. The structure of ibuprofen is
given below. What is the molecular formula of
ibuprofen?
C13H18O2
H
H C HH
H
HO
C
C
H
C
C
CH C H
H
H
O
C
C
C
H
C
C
C
H H
H H H H
ibuprofen
Ibuprofen is the active ingredient in a number
of analgesics. The structure of ibuprofen is
given below. What is the molecular formula of
ibuprofen?
C13H18O2
HO
O
ibuprofen
The three dimensional nature of molecules,
such as ibuprofen, is fundamental to all of
their properties including biological behavior.
C13H18O2
Bonding and Molecular Structure
Structural formulas of organic compounds
structural formula
condensed formula
line-angle formula
H H H H H
H C
C C C
C H
CH3CH2CH2CH2CH3
H H H H H
H H OH H
H C
C C C H
H H H H
H O H
H C C
H
C H
H
CH3CH2CHCH3
OH
CH3CH2CH(OH)CH3
OH
O
CH3CCH3
CH3COCH3
(CH3)2CO
O
Draw the first two compounds in a bond-line formula. Draw the
second two compounds in a condensed formula.
(CH3)3CCH2CH2CH(CH3)2
OH
CH3CH2C(CH3)2CH(OH)CH2CH2CH2Cl
OH
Br
Draw the first two compounds in a bond-line formula. Draw the
second two compounds in a condensed formula. Click on the arrow to
check your answer.
Cl
OH
(CH3)3CCH2CH2CH(CH3)2
CH3CH2C(CH3)2CH(OH)CH2CH2CH2Cl
(CH3)2CHCH2C(CH3)2CH(OH)CH(Br)CH3
OH
OH
OH
H 2C
H 2C
CH
CH2
CH2
CH2
Br
Petroleum
products
Petroleum
products and
the ranges of
hydrocarbons
in each
product