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IB Chemistry: Topic 10: Organic Chemistry

Organic Quiz One, Review

Be familiar with the following—while the quiz may not cover all of the topics, everything below is basically
what has been covered in the course as of yet. Refer to previous guides for additional details on certain
materials.

POTENTIAL TOPICS

− Nomenclature: be able to draw structures, given a name; or vice versa

− Homologous series: alkanes, alkenes, alkynes
− Hydrocarbons: physical/chemical characteristics
o Saturated versus Unsaturated
o Substituent groups—alkyls
o Benzene
o Cyclic Forms
− Functional Groups
o Alcohol
o Halide
o Ester
o Ketone
o Amide
o Amine
− Combustion
− Video Clip

Homologous Series

A homologous series is one in which all the members have the same general formula. The neighboring
members in one series differ by one —CH2— and show similar chemical properties and a gradation in their
physical properties.

Alkanes follow the general formula ‫ܥ‬௡ ‫ܪ‬ଶ௡ାଶ and consists solely of single bonds.

Alkenes follow the general formula ‫ܥ‬௡ ‫ܪ‬ଶ௡ and contain at least one carbon-carbon double bond. Note that
more complex alkenes will have more than one carbon-carbon double bond. The general formula only refers
to alkenes with one double bond.

Alkynes follow the general formula ‫ܥ‬௡ ‫ܪ‬ଶ௡ିଵ and contain at least one carbon-carbon triple bond.

Hydrocarbons

As their name suggestions, hydrocarbons are organic compounds containing exclusively hydrogen and
carbon atoms. Hydrocarbons are divided into aliphatic compounds and aromatic compounds. Aromatic
structures contain benzene rings or similar structures, while aliphatic compounds do not incorporate
aromatic rings.
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IB Chemistry: Topic 10: Organic Chemistry

Organic Quiz One, Review

When compared to other organic materials, hydrocarbons are relatively unreactive. However, most
hydrocarbons are flammable, burning in oxygen to produce carbon dioxide and water vapor. They will also
undergo substitution reactions in the presence of ultraviolet light. Hydrocarbons with double bonds will
undergo addition reactions.

Saturated hydrocarbons have the maximum number of hydrogen atoms possible—alkanes are saturated.
Unsaturated hydrocarbons do not have the maximum number of hydrogen atoms. Alkanes and alkynes are
examples of unsaturated hydrocarbons.

Alkyl groups are another way to refer to substituent groups, or branches from the parent chain. One
example of an alkyl is a methyl group, which has the formula CH3. The name of these branches typically go
before the parent chain (e.g. methylpropane).

The benzene ring contains 6 carbon atoms and 6 hydrogen atoms—one would expect it to have three
carbon-carbon double bonds. However, its unexpected stability is due to its resonance structure: its bonds
are intermediate between a typical single bond and double bond.

Benzene can be depicted in various ways: as either drawing alternating double

bonds or using a hexagon and drawing a circle in the center to represent the
delocalized electrons.

Cycloalkanes have the general formula ‫ܥ‬௡ ‫ܪ‬ଶ௡ , as compared to the

alkanes’ general formula of ‫ܥ‬௡ ‫ܪ‬ଶ௡ାଶ. The additional carbon-carbon bond
reduces the amount of hydrogen atoms. Cycloalkanes are saturated.
Examples of unsaturated cyclic hydrocarbons are cyclopentene and
cyclobutene.

An alternative way to depict cyclic forms is to use the condensed

structure, which uses basic shapes—each vertex represents a carbon
atom.
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IB Chemistry: Topic 10: Organic Chemistry

Organic Quiz One, Review

Functional Groups

Name Formula Prefix Suffix

Alcohol Hydroxy- -Ol
Halogen F- Fluoro- N/A
Cl- Chloro-
Br- Bromo-
I- Iodo-
Ester N/A -Oate

Aldehyde Oxo- -Al

Ketone Oxo- -One

Amine Amino- -Amine

Amide N/A -Amide

Combustion

Combustion of hydrocarbons is the burning of hydrocarbon in the presence of oxygen gas. It is an

exothermic reaction that produces heat, carbon dioxide, and water.

Complete combustion occurs when there is sufficient oxygen available and produces a blue flame.
Combustion is a type of redox reaction: carbon is oxidized and oxygen is reduced.

Incomplete combustion occurs when there is insufficient oxygen available. A smoky, yellow flame is
produced, along with carbon, carbon monoxide, and other hydrocarbons that did not completely burn. The
black soot is carbon and the yellow flame comes from glowing carbon atoms.

Carbon monoxide is toxic for humans because it binds to the hemoglobin in red blood cells in the
spots where oxygen usually binds. Unlike oxygen, it is never released and can cause suffocation if
enough sites on the hemoglobin are blocked.

Unburned hydrocarbons can also react with other molecules in the air, such as nitrogen dioxide,
creating ozone, which is toxic for humans to breathe. Particulates in the air from unburned
hydrocarbons can also impair breathing ability.

To balance combustion reactions, first balance the carbons and then balance the hydrogens. If an odd
number of oxygen molecules are necessary, double all coefficients in the reaction.
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IB Chemistry: Topic 10: Organic Chemistry

Organic Quiz One, Review

Video Clip

Crude oil is composed of a mixture of several types of

hydrocarbons. Fractional distillation,
distillation via heat, is used to
separate the components. The largest (heaviest) hydrocarbons
have higher boiling points, while the smaller (lighter)
hydrocarbons have low boiling points. In a fractional distillation
column, the temperature is highest at the bottom and lowest at
the top. There are trays at various temperature levels to collect
the components as they rise to a temperature lower than their
boiling point and condense. The bubble caps on the trays help
collect the vapor.

Bitumen and paraffin are two of the heaviest substances. At

260°C, the diesel oil condenses. At 180°C, kerosene condenses. At
110°C, petrol condenses.

Cracking is the breaking of carbon-carbon bonds to make smaller

chains from larger carbon chains. The basic concept is to heat the
compound. There are different types of cracking, with the most
efficient method being catalytic cracking.
cracking

The four main types of cracking are thermal, steam, hydro, and catalytic.

− Thermal: The oldest type of cracking, it involves heating hydrocarbons to 750-900°C at a pressure of
700 kPa. It produces alkenes and leaves a heavy residue.
− Hydro: Hydrocarbon chains are broken in highly pressurized hydrogen—5000 kPa. This produces
kerosene, gasoline, and liquefied petroleum gas (LPG) .
− Steam: A gaseous or liquid hydrocarbon is diluted with steam and heated to 850°C without the
presence of oxygen. The reaction takes place only briefly and produces lighter alkenes, which are
used in plastics manufacturing.
− Catalytic (“Cat”): Catalytic cracking is the most effective method and involves using an acid
catalyst to assist in breaking down the hydrocarbons. It takes place in an oxygen-free environment
at 500°C. One common catalyst is zeolite, which, like all catalysts, is not consumed in the reaction
and can be reused. Catalytic cracking produces smaller alkanes used in petrol.

Octane rating refers to the percentage of octane in gasoline: for example, gasoline of a 91 octane rating is
91% octane and 9% heptane. Octane’s official name is 2, 2, 4-trimethylpentane: it is a branched hydrocarbon
chain that is more complex than a simple heptane molecule. As a result, it is more expensive to create and
more expensive to purchase. Octane is more high quality than heptane and burns smoothly. Heptane may
ignite too quickly and burn with small explosions.