Chapter 24

Organic Chemistry

Organic chemistry is the study of carbon compounds excluding CO, CO2, CS2, bicarbonates,
carbonates, and cyanides. Upon completion of this chapter, your students should be able to:

1. Write the general formula and provide examples for each of the following organic functional
groups:
• alkane
• alkene
• alkyne
• cycloalkane
• aromatic
• alcohol
• ether
• aldehyde
• ketone
• carboxylic acid
• ester
• amine
2. Use IUPAC rules to name the following:
• alkanes
• alkenes
• alkynes
• aromatics
3. Draw and name all of the possible isomers given the chemical formula of an alkane.
4. Use the following groups in naming organic compounds:
• methyl
• ethyl
• n-propyl
• n-butyl
• isopropyl
• t-butyl
• amino
• fluoro
• chloro
• bromo
• iodo
 • nitro
• vinyl
5. Define a free radical and show by a chemical reaction the steps in which chlorine can be used
to generate free radicals.
6. Cite an example of a substituted alkane that is optically active. Specify cis and trans to
geometric isomers of alkenes.
7. Use the terms olefin, unsaturated, and addition reaction to describe the properties and
reactions of alkenes.
8. Predict polarity and expected boiling point trends for geometric isomers.
9. Describe the concept of resonance in aromatic compounds.
10. Explain why aromatic compounds undergo substitution reactions rather than addition
reactions.
11. Give the chemical formulas for the following:
• wood alcohol (methanol)
• ethyl alcohol (ethanol)
• rubbing alcohol (2-proponol or isopropanol)
• ethylene glycol
12. Explain how a condensation reaction is characterized.
13. Define carbonyl and cite an example of the difference in the chemical structures of aldehyde
and ketone.
14. Write the chemical structure for acetic acid, the acid found in vinegar.
15. Write a chemical equation that demonstrates saponification of an ester.
16. Describe what is meant by octane number of gasoline and cite two examples of antiknocking
agents that have been used (tetraethyllead and MTBE).

Section 24.1 Classes of Organic Compounds

Over 13 million organic compounds are known. In order for your students to begin to understand
this huge field, it is important that they become familiar with several of the major functional
groups. The chemical behavior of most organic compounds is determined by the functional
groups that are present. In addition, the functional groups dictate the correct name of the
compound.

Section 24.2 Aliphatic Hydrocarbons

Hydrocarbons, organic compounds containing only carbon and hydrogen, are classified as
aliphatic or aromatic. Aromatic compounds contain the benzene ring. The aliphatics are the
alkanes, alkenes, cycloalkanes, and alkynes.
The recommended nomenclature for organic compounds is a series of prefixes and
suffixes joined together. The prefix methyl refers to one carbon, ethyl to two carbons, propyl to
three carbons, etc. The suffix -ane suggests only single carbon bonds, -ene suggests carbon-
carbon double bonds, and -yne suggests carbon-carbon triple bonds. It may be easier for your
students to understand the numbering system for organic compounds if you use halogens on
various positions of straight-chain molecules before you begin branching. For example,

BrCH2CH2CH2CH2CH3 1-bromopentane

2-bromopentane

3-bromopentane

1,2-dibromopentane

3,3-dibromopentane

Once your students are comfortable with placing bromine on various positions, have them
combine Br and Cl. Finally, after they have mastered that, begin substituting methyl or ethyl
groups. Your students should understand that a straight-chain alkane is not really straight in
nature. To illustrate the point, use the analogy that a piece of string wadded into a ball would be
considered a straight chain because it has no branches.
One can demonstrate the halogenation of alkanes by using a “black light”. The procedure
is to add a few drops of bromine dissolved in carbon tetrachloride to two test tubes containing an
alkane, such as hexane. The solutions will be an amber color. If one of the tubes is placed under
the ultraviolet light for approximately fifteen minutes, the amber color of the bromine solution
will dissipate indicating that the Br2 has reacted with the alkane. The solution that is not exposed
to ultraviolet light will remain amber-colored.
We encountered optical isomerism in our study of coordination compounds. It is easy to
show optical isomers in organic chemistry by using molecular models. To do this, assemble two
CHFCl Br models (these two models need to be identical). Now, interchange any two atoms on
one of the models. The result is a nonsuperimposable mirror image of the first model. These two
compounds would be optical isomers and would rotate plane-polarized light differently.
 You may wish to point out that cycloalkanes have the same general formula as alkenes,
CnH2n; however, they have considerably different reactivities. An easy demonstration is to add a
few drops of aqueous potassium permanganate to two or three milliters of cyclohexane and to
hexene. The cyclohexane will not react, but the double bond in the hexene will react with the
potassium permanganate to convert the purple solution to a brown precipitate of manganese
dioxide. This same demonstration can be used to show that toluene (methylbenzene) does not
contain carbon-carbon double bonds as is found in hexane. The toluene will behave similarly to
cyclohexane and not react with potassium permanganate.

Section 24.3 Aromatic Hydrocarbons

Your students have seen benzene, the simplest aromatic compound, previously when we
discussed resonance and delocalized molecular orbitals. It has been shown earlier that aromatic
compounds do not usually react via addition reactions as those compounds containing carbon-
carbon double or triple bonds do; rather, aromatic compounds prefer substation reactions. Many
of the polycyclic aromatic compounds are carcinogens, which require them to be handled with
special care.

Section 24.4 Chemistry of Functional Groups

Ethanol can be converted to acetic acid using acidified dichromate. This is a very visual reaction
in that the orange dichromate solution is converted to a forest-green solution upon reaction with
ethanol. This is the same principle on which the alcohol breathalyzer tests are based. It should be
noted that the suffix for alcohol is -ol.
When ethanol is oxidized, it can form acetaldehyde or acetic acid. The suffix for
aldehyde is -al.
The accepted suffix for ketone is -one. A very common ketone found in industry is
methyl ethyl ketone (MEK). It is used as a solvent in a variety of applications including solvents
for paints and coatings.