Ms. Capasso’s Awesome Organic Chemistry Review Sheet!
Organic Chemistry is the study of carbon and its compounds.
 Carbon has four valence electrons and therefore can make four different
bonds
 Carbon can make infinitely complex chains and rings leading to a wide
variety of complex molecules which is important for sustaining life
Vocabulary
 Hydrocarbon – a compound that only has hydrogen and oxygen; examplepropane
 Aliphatic – a straight-line carbon chain
 Cyclocarbon – a carbon chain that is in a closed ring
 Aromatic carbon – a carbon ring that contains alternating single and double
bonds leading to a delocalized system of pi bonds
 Substituents (side-chains) – a group of atoms that branch off of the main
carbon chain
 IUPAC – the International Union of Pure and Applied Chemistry; refers to the
governing body which makes globally recognized naming convention for
organic molecules
 Functional Group - any group that replaces a hydrogen in a hydrocarbon
chain leading to different physical and chemical properties for that group
Saturated
 Compounds which contain only
single bonds
 Alkanes
Unsaturated
 Compounds which contain double
or triple bonds
 Alkenes, alkynes
Homologous Series:
 Organic compounds may be grouped into “families” of compounds known as
homologous series
 The members of each homologous series contain certain common features
and/or general formula
 We learned about three homologous series: alkane, alkenes and alkynes
Family
Alkanes
Alkenes
Alkynes
General
Formula
CnH2n+2
CnH2n+2
CnH2n-2
Saturated or
Unsaturated
Saturated
Unsaturated
Unsaturated
Bonds
Naming
All single
One double
One triple
End in –ane
End in –ene
End in -yne
If the third member of a family is C3H8 than the fifth member is C5H12
Physical Properties – Organic Compounds
1. Mostly non-polar
2. React slower than inorganic compounds
3. Almost all covalent compounds
4. Weak intermolecular forces* (London Dispersion)
5. Low melting point and low boiling point
6. Not soluble in water
*The exception being those compounds that contain hydrogen bonds
Within a homologous series, as the molecules get bigger, the intermolecular
forces (London Dispersion) get stronger and melting point and boiling point
get higher! Example: Decane has a much higher boiling point than methane!
Formulas for organic compounds:
Empirical
Shows the simplest whole number ratio of the atoms it
contains
Example: CH2O
Molecular
Shows the actual number of atoms of each molecule contained
in the compound
Example: C6H12O6
Structural
Shows how the atoms are bound together
Within structural formulas, there are three different types:
Full Structural
Shows exactly how the atoms are bonded together
Condensed
Structural
Omits showing bonds and instead tries to unambiguously
show the structure of the molecule with minimal information
Stereochemical
Example: CH3CH2CH2CH2CH2CCCH2CH3 is 3-nonyne (alkyne)
Attempts to show position of atoms and three dimensional
position in space; do not need for Regents
Nomenclature – IUPAC Naming
 IUPAC naming conventions give all scientists a logical way to name organic
compounds
Steps
1. Identify the longest hydrocarbon chain and give it a prefix (i.e. meth, eth, pro,
etc.)
2. Identify the functional groups and give them a name. This can be either some
sort of prefix (i.e. cloro, methyl, etc.) or a suffix change (i.e –ol for alcohols)
3. Identify any side chains and give them a name (i.e. methyl, ethyl, etc.)
4. Number your carbons left to right and right to left. Choose the numbering
that gives the functional groups, side chains and multiple bonds the lowest
numbers possible. Choose only one way!
5. Give each of your functional groups, side chains and multiple bonds a
number based on what carbon they are bound to
6. Complete your name by choosing the proper suffix based on the functional
group or double/triple bonds
Isomers
 Isomers are compounds that have the same molecular formula but a different
structural formula
 Example: C5H12
Three Isomers
Functional Groups
 Functional groups can be found on Table R
 Naming conventions can be gathered by looking at Table R; derive their
name from the un-substituted carbon chain
Functional
Group
Halide
What is it?
Alcohol
-O-H (hydroxyl group)
attached to carbon chain
-Br -I -F -Cl attached to a
hydrocarbon
How is it named?
Why is it
important?
“1-chloro”
Used in
With a number and refrigerators and
a name before the
as propellants
parent chain
Organic solvents
and pesticides
Changing the -e in
Cleaning, fuel and
the ending to -ol
beverages
Ether
-O-
Aldehyde
-C=O
H
Ketone
Organic
Acid
Ester
Common way –
Anesthesia
(Regents does not
go into IUPAC_ name both side
chains and then
say “ether”. No set
rules on which one
goes first!
Change the final “e” Smell good; vanilla
to “al”
and cinnamon
A carbon with one double
bond to an O. Only bound
to one other carbon
-C=O
|
E.g. propanal
A carbon bound to two
other carbons and also
double bound to oxygen
-COOH
E.g. propanone
Carbon double bound to
an O and single bound to
an O-H group
-COOCCarbon double bound to
an O and single bound to
another C and an O
Amine
-N-
Amide
Nitrogen bound to carbon
with single bonds
R-C-N-R’
||
O
Change the final “e” Great solvents!
to “-one”
Change the ending
to “oic acid”
Acids! Used in a lot
of biochemical
reactions keeping
us alive
The compound
that used to be the
acid gets it ending
changed to “-oate”
and the other
named before
Smells good –
bananas,
wintergreen,
pineapple, etc.
Change final “e”
and add “-amine”
Important in
Biology – B
vitamins,
hormones, etc.
Important for life!
Also called a
peptide bond
because it holds
proteins together
E.g. methamine
Also called a
peptide linked.
Only when
terminal, change
final “e” and add “-
amide”
Alcohols:
 Can be classified as primary, secondary, or tertiary depending on what
carbon the hydroxyl (-OH) group is bound to
 Can also be classified for how
many hydroxyl groups there are in
Primary – the carbon –OH is
a molecule
attached to only attached to one
other carbon
Secondary – the carbon –OH is
attached to attached to two other
C’s
Tertiary – carbon –OH attached to
attached to 3 other C’s
Trihydroxyl Alcohol
Amino Acids
 Contain an organic acid group and an amine group
 Connect together using condensation or dehydration synthesis; resulting
bond is an amide
 Building block of proteins!
Organic Reactions
 Combustion – Burning a hydrocarbon in oxygen until it makes CO2 plus H2O

Substitution - Saturated hydrocarbons have all their bonding sites filled
with hydrogen. In substitution, one of the hydrogen atoms is replaced with
something else (Example: One of the halogens (Group 17) replaces a
hydrogen - Br, Cl, or OH)

Addition – When two atoms are adding across a double or triple bond

Fermentation – Alcohol formed by yeast breaking down sugar; yeast cells
secrete an enzyme called zymase which breaks down the six-carbon chain of
sugar into CO2 and two alcohol molecules

Esterification – Esters form from the reaction of an organic acid and alcohol
by the removal of one water molecules

Saponification – The hydrolysis of fats by bases to make a soap and a salt; an
ester reacts with an inorganic base like NaOH to make soap and a salt

Polymerization – Small molecules (monomers) are combined to make larger
molecules of repeating units called polymers
o Condensation: Polymer forms by the removal of water
o Addition: Involves the opening up of double or triple bonds