Macromolecules

Libby Kunst, Emma Soetebier,

and Aimun Amatul-Hayee
Organic Chemistry: From Vitalism to Mechanism
Organic Chemistry- the branch of
chemistry specializing in the study
of organic compounds
Friedrich Whler (1828)
Artificial Synthesis Ammonium Cyanate
Vitalism-belief in a life force Hermann Kolbe
outside of chemical and Acetic Acid
physical laws Mechanism- belief that physical
Jons Berzelius and chemicals laws govern all
natural phenomena
Stanley Millers Experiments
Stanley set out to see if complex organic
molecules could be spontaneously
generated under conditions of the early
Earth
Miller observed that a variety of organic
molecules are common in organisms
Formaldehyde
Hydrogen Cyanide
Amino Acids
Hydrocarbons**
Carbon Bond Formation
When a carbon atom

Forms four single covalent bonds, it

creates a tetrahedron
Single bonds are extremely flexible
Forms a covalent bond with another
carbon at the center of the molecule, it
creates two connected tetrahedron
groups
Forms a double bond with another
carbon, it creates a molecule with atoms
on the same plane (Planar)
Double bonds are more rigid
 Structural Models Recognized on the AP Exam
Methane: CH4

Ball-and-Stick Model Space-filling Model Simple Drawing

Variations in Carbon Skeleton
Length:
1 ~ Meth
2 ~ Eth
3 ~ Prop
4 ~ But
5 ~ Pent
Branching:
Meth Methyl
Prop Propyl
Double Bonds:
1-Butene
2-Butene
Rings:
Each corner of the ring
represents a carbon and its
attached hydrogens
Hydrocarbons
Hydrocarbons- organic molecules consisting
of only carbon and hydrogen

Characteristics of Hydrocarbons:
NOT prevalent in organisms- fats have a
hydrocarbon tail attached to
non-hydrocarbon component (most) 1 Million
Can undergo reactions that produce a Years
great amount of energy (Fat Energy
for humans/ Gasoline Energy for cars)
Hydrophobic due to their general
polarity
PETROLEUM (partially decomposed
organic material from millions of years
ago)
 Break: S
earch Re
sults for
Isomers: *Confusion Level Increased*
Carbon
Skeleton

Two compounds could have the same

molecular formula but one could be
branched and the other straight

Three Types:

Structural Isomers

Geometric Isomers

Enantiomers
Structural Isomers
Structural isomers differ in the covalent
arrangements of their atoms
As the number of carbons in the
...
backbone increases, the number of
possible isomers also increases
Common Misunderstandings
Isomers are the different types of
arrangements per every ONE molecular
formula
C5H12 has 3 isomers
C8H18 has 18 isomers
C20H42 has 366,319 isomers
Geometric Isomers
Differ in the arrangement of double
bonds

...
Single bonds allow for rotation and
flexibility, while double bonds are stuck
If double bond joins two carbon atoms
and each carbon atom has another
group of atoms attached to it two
Cis Trans
geometric isomers possible

Cis Isomers Trans Isomers

*Rs represent atom attached to

double-bonded carbons*
Enantiomers
Isomers that are mirror images of each

other
Asymmetric Carbon- carbon attached to
four atoms or groups of atoms
Atoms are spatially arranged around the
asymmetric carbon
...
The two resulting isomers are
distinguished as the L isomer and the
D isomer
L isomer = levo (left)
D isomer = Dextro (right)
Molecules in the cell can differentiate
the two by shape
One is usually biologically active and the
other is dormant
Enantiomers in Pharmaceuticals
A drugs L and D isomers can produce
extremely different effects due to the
spatial arrangements of the atoms
Remember how we said one isomer is
biologically active and the other was
dormant? This is the case
Effective Enantiomer or Ineffective
Enantiomer
Ibuprofen~
S-Ibuprofen = Effective
R-Ibuprofen = Ineffective
S-Ibuprofen is 100x more effective
Over-the-counter Ibuprofen is a
combination of the two