ORGANIC CHEMISTRY

Organic Chemistry: study of carbon and carbon compounds; there are a lot of
carbon compounds. The C atoms bond together to form chains or rings.
Common Characteristics:

1.Generally non-polar (wont dissolve in water)

2.Soluble in non-polar solvents
3.Non-electrolytes.
4.Low melting points
5.Reactions generally slower than inorganic compounds
6.Reactions have higher activations energies (therefore slower reactions)

Carbon has 4 valence electrons and therefore can form 4 covalent bonds around them
(remember single, double or triple)
Hydrocarbons: contain carbon and hydrogen atoms.

Table P &Q: Table P indicates the prefix used based on the # of carbons.

ALKANE: (-ane)
Hydrocarbons are made up of only single bonds, and are therefore considered
saturated.

ALKENE: (-ene)
Alkenes have one double bond and classified as unsaturated.

ALKYNE : (-yne)
Alkynes have one triple bond and are considered unsaturated.

Condensed Formulas: Taking an organic compound, and shortening the

chemical formula. Same compound, just written differently.
Alkyl Group: (-yl)
Also hydrocarbons, known as side chains.
Have one less hydrogen then a corresponding alkane.

CH3
C2H5
C3H7
C4H9
C5H11
C6H13
C7H15
C8H17
C9H19
C10H21

SUMMARY ON HOW TO DRAW CARBON COMPOUNDS:

1. Look at the prefix (table P), which will tell you the number of carbons.
2. Put the bonds between the carbons (-ane = single bonds; -ene = double bond; and
yne means a triple bond)
3. The number before ene and yne tells you where the double or triple bond is
after that carbon atom, Ex: 2-pentene (db after 2nd carbon), or 1-butyne (tb after
1st carbon).
4. When needed, if you have an alkyl group like methyl (CH3), the number before
tells you which carbon atom to put it on; Ex: 2-methyl (put the methyl on the 2nd
carbon).
5. Put all of the appropriate hydrogen atoms around the carbon atoms if they belong
there.

Pentane 2-Pentene 2-Pentyne

ISOMERS: compounds that have the same molecular formula but different structural
formula.
The rule to naming these structures is to count the number of carbon atoms in the
longest unbroken chain. You want to use the lowest possible number, so this
means you might have to count from the left to right or from right to left.
2-methyl butane
2,2 dimethyl propane

Pentane
OTHER ORGANIC COMPOUNDS & FUNCTIONAL GROUPS (Table R):

Alcohols: (OH)
The OH in an alcohol is a hydroxyl, and the OH- in a base is a hydroxide ion;
ALCOHOLS ARE NOT BASES.
To name an alcohol, drop the e from the corresponding alkane and all ol.
OH can be placed on any carbon and therefore a number is required to indicate on
which carbon its on when there are 3 or more carbons in a chain.
Diol (2 OH are present); triol (3 OH are present)

Ether:
You name this compound by using the word ether at the end and use the name
of the alkyl groups attached at both ends.
Alcohols and Ethers make isomers of each other when there are the same number
of carbons atoms.

Aldehyde: (CHO)
Named by dropping the final e in an alkane and adding al.
Found at the end, no number required.

Ketone:
Ketones are named by dropping the final e from the corresponding alkane and
adding one.
The double bonded oxygen MUST be on an inside carbon, and therefore, requires
a number to indicate on which carbon its attached to on the chain.
Aldehydes and Ketones make isomers of each other when there are the same
number of carbon atoms.

Organic Acids: (COOH)

Named by dropping the final -e from the corresponding alkane and adding oic
acid.
Functional group at the end, and therefore, no number is required.

Halides: (F, Cl, Br, I)

Name it by using a number to state which atom the halogen is being attached to,
then use the prefix for that halogen (fluoro-, chloro-, bromo-, iodo-) and end with
the appropriate alkane.
There can be multiple halides so its necessary to use a number to indicate which
carbon(s) they are on. Use prefixes like di, tri, etc if there are more than one of
the same kind of halogen.

Amine:
Named by dropping the final e in the hydrocarbon and adding amine.
Can be placed on any carbon, so a number is required.
Amide:
Named by dropping the final e in the hydrocarbon and adding amide.
Functional group at the end, therefore no number is required.

Ester: (COO)
Esterfication Alcohol + Acid Ester + Water

How to name:
1. Name the part that came from the alcohol first using an alkyl name
depending on how many carbon atoms there were.
2. Name the part that came from the acid second by naming it like an alkane
depending on the number of carbons, dropping the ane, and adding the
ending oate.
Effects of Functional Groups on Boiling Point

1.Alcohols and Acids: Have the highest BP because they are held together with
hydrogen bonding.

2.All other functional groups: Next highest BP.

3.Hydrocarbons: Weakest BP.

Examples: Methanol Methanal Methane (highest to lowest BP)

ORGANIC REACTIONS:

Substitution: Occurs in ALKANES only.

2 reactants and 2 products.

Addition: Happen only to ALKENES & ALKYNES. Breaking a double to a single or

a triple to a double.
2 reactants and 1 product.

Fermentation: Glucose is broken down into ethanol and carbon dioxide (Anaerobic
Respiration).

Esterfication: Alcohol + Acid Ester + Water

Saponification: Reverse of esterification. This process produces SOAP.

Combustion: First 6 reactions on Table I.

Organic Compound + O2 CO2 + H2O
Polymerization: involves smaller molecules joining together to form one big molecule.
A polymer is a large molecule made up of multiple monomers.
condensation: polymerization by dehydration synthesis (removing water) to
form a polymer. Ex: nylons, polyester. Naturally occurring polymers include
starches and protein.
addition: polymerization joining together by breaking a double or triple bond.
Name __________________ Chap. 8 Organic Review Constructed Response

Base your answers to questions 1 and 2 on the information below and on your knowledge of
chemistry.

Natural gas and coal are two fuels burned to produce energy. Natural gas consists of
approximately 80% methane, 10% ethane, 4% propane, 2% butane, and other
components.
The burning of coal usually produces sulfur dioxide, and sulfur trioxide,
, which are major air pollutants. Both and react with water in
the air to form acids.
1. Draw a structural formula for the hydrocarbon that is approximately 2% of natural gas.

2. Write the general formula for the homologous series that includes the components of the
natural gas listed in this passage.

3. Base your answer to the following question on the information below and on your knowledge
of chemistry.

Ethane, , has a boiling point of at standard pressure. Ethanol, ,

has a much higher boiling point than ethane at standard pressure. At STP, ethane is a gas
and ethanol is a liquid.
Identify the class of organic compounds to which ethanol belongs.

Base your answers to questions 4 and 5 on

information below.

One type of soap is produced when ethyl stearate and sodium hydroxide react. The
soap produced by this reaction is called sodium stearate. The other product of the reaction
is ethanol. This reaction is represented by the balanced equation below.

4. To which class of organic compounds does ethyl stearate belong?

5. Identify the type of organic reaction used to make soap.

Chap. 8 Organic Review

6. Two hydrocarbons that are isomers of each other are represented by the structural formulas
and molecular formulas below.

Explain, in terms of structural formulas and molecular formulas, why these hydrocarbons are
isomers of each other.

Base your answers to questions 7 and 8 on the information below.

A reaction between bromine and a hydrocarbon is represented by the balanced equation

below.

7. Write the name of the homologous series to which the hydrocarbon belongs.

8. Identify the type of organic reaction.

9. Base your answer to the following question on the information below.

In one industrial organic reaction, C 3H6 reacts with water in the presence of a catalyst.
This reaction is represented by the balanced equation below.

Explain, in terms of bonding, why C3H6 is classified as an unsaturated hydrocarbon.

Chap. 8 Organic Review

10. Base your answer to the following question on the information below.

Biodiesel is an alternative fuel for vehicles that use petroleum diesel. Biodiesel is
produced by reacting vegetable oil with CH3OH. Methyl palmitate, C 15H31COOCH 3, a
compound found in biodiesel, is made from soybean oil. One reaction of methyl palmitate
with oxygen is represented by the balanced equation below.

2C15H31COOCH3 + 49O2 34CO2 + 34H2O + energy

Identify the type of organic reaction represented by the balanced equation.

11. Base your answer to the following question on

the information below.

Gasoline is a mixture composed primarily of

hydrocarbons such as isooctane, which is also
known as 2,2,4-trimethylpentane.
Gasoline is assigned a number called an
octane rating. Gasoline with an octane rating of
87 performs the same as a mixture that consists
of 87% isooctane and 13% heptane.
An alternative fuel, E-85, can be used in
some automobiles. This fuel is a mixture of 85%
ethanol and 15% gasoline.
In the space below, draw a structural formula for
a molecule of 2,2,4-trimethylpentane.
Chap. 8 Organic Review

Base your answers to questions 12 and 13 on

the following information.

The equation below represents the reaction between butanoic acid and an unidentified
reactant, X.

12. Draw a structural formula for the unidentified reactant, X, in the equation.

13. Identify the type of organic reaction represented by the equation.

Base your answers to questions 14 and 15 on the information below.

Given the balanced equation for an organic reaction between butane and
chlorine that takes place at 300.C and 101.3 kilopascals:

C4H10 + Cl2 C4H9Cl + HCl

14. Draw a structural formula for the organic product.

15. Identify the type of organic reaction shown.

Answer Key
Organic Chemistry

1. 11.

12.
2.
3. alcohol alcohols
primary alcohol
monohydroxy
alcohols
13. Examples:
4. ester or esters
esterification
5. saponification dehydration
6. The molecular synthesis
formulas of the 14.
two hydrocarbons
are the same, but
the structural
formulas are
different.
7. alkene or
alkenes. 15. Examples:
8. addition substitution
halogenation chlorination
bromination halogenation
9. Acceptable
responses include,
but are not limited
to: The C 3H6 is
unsaturated
because each
molecule has a
double covalent
bond between two
of its carbon
atoms. There is a
carbon-carbon
double bond in
each molecule
10. Example:
combustion