Chemistry and Physiochemical

Properties of Alkanes
Lecture # 04 (Part-II)
Properties of Alkanes
• Alkanes are saturated hydrocarbons, that is all of the carbon atoms are ‘saturated’ with
hydrogen atoms and do not contain any carbon-carbon double bonds or triple bonds.

• Alkanes are the simplest and least reactive hydrocarbon species containing only carbons
and hydrogens.

• They are commercially very important, being the principal constituent of gasoline and
lubricating oils and are extensively employed in organic chemistry; though the role of pure
alkanes (such as hexanes) is delegated mostly to solvents.

• Because alkanes have relatively predictable physical properties and undergo relatively
few chemical reactions other than combustion, they serve as a basis of comparison for
the properties of many other organic compound families.
Physical
Properties
of Some
Alkanes • Table describes some of the properties of the first 10
straight-chain alkanes. Nearly all alkanes have densities
less than 1.0 g/mL and are therefore less dense than
water (the density of H2O is 1.00 g/mL at 20°C).
 Melting Points and Boiling Points
• Both the melting points and boiling points of alkanes are characteristic of the
intermolecular forces found between the molecules.
• The electronegativity difference between carbon and hydrogen (2.1 – 1.9 = 0.2) is
small; therefore, the C-H bond is nonpolar, meaning that the only attractions
between one molecule and its neighbors will be London dispersion forces.
• These forces will be very small for a molecule like methane but will increase as
the size of the molecules increase.
• Therefore, the melting and boiling points of the alkanes increases with the
molecular size, due to the increase in London dispersion forces. (i.e. the
intermolecular forces are stronger in larger hydrocarbons, therefore, more energy
is required to cause phase changes).
Melting Points and
Boiling Points for
Straight Chain Alkanes

Figure shows the melting and boiling

point trends for the first 16
hydrocarbons.

Notice that the first four alkanes are

gases at room temperature, and
solids do not start to appear until
about C17H36.
Regarding isomers, the more branched the chain, the lower the boiling point tends
to be. London dispersion forces are smaller for shorter molecules and only operate
over very short distances between one molecule and its neighbors.

It is more difficult for short, bulky molecules (with substantial amounts of

branching) to lie close together (compact) compared with long, thin molecules.

Cycloalkanes are similar to alkanes in their general physical properties, but they
have higher boiling points, melting points, and densities than alkanes. This is due to
stronger London forces because the ring shape allows for a larger area of contact.
Problem
• Without referring to a table, predict which has a higher
boiling point—hexane or dodecane. Explain.
Solubility
• Alkanes (both normal and cycloalkanes) are virtually insoluble in water but dissolve in
organic solvents.
• The liquid alkanes are good solvents for many other covalent compounds.
• When a molecular substance dissolves in water, the following must occur:
✓ Breaking of the intermolecular forces within the substance. In the case of the alkanes,
these are the London dispersion forces.
✓ Breaking of the intermolecular forces in the water so that the substance can fit between
the water molecules. In water, the primary intermolecular attractions are hydrogen bonds.
• Breaking either of these attractions requires energy, although the amount of energy
required to break the London dispersion forces in a compound, such as methane,
is relatively negligible; this is not true of the hydrogen bonds in water. Recall that
hydrogen bonds are much stronger.
To simplify, a substance will dissolve if sufficient energy is
released when the new bonds are formed between the
substance and the water to make up for the energy
required to break the original attractions.
The only new attractions between the alkane and the water
molecules are the London dispersion forces. These forces
to do not release a sufficient amount of energy to
compensate for the energy required to break the hydrogen
bonds in water. Therefore, the alkane does not dissolve.
Long Chain Hydrocarbons are Insoluble in Water.
Neither the saturated and unsaturated
hydrocarbons in this sunflower oil do not have
strong enough intermolecular forces to disrupt the
hydrogen bonds between the water molecules.
Thus, the oil is not soluble in the water and forms
beaded bubbles of oil at the surface of the water/oil
interface.
In this case the oil is less dense than the water and
will float on top of the water layer.
Solubility in organic solvents
• In most organic solvents, the primary forces of attraction between the solvent
molecules are the London dispersion forces.

• Therefore, when an alkane dissolves in an organic solvent, the London

dispersion forces are broken and are replaced by new London dispersion forces
between the mixture.

• The two processes more or less cancel each other out energetically; thus, there
is no barrier to solubility.
 • Alkanes are nonpolar compounds
that are insoluble in water.

Key Takeaway
Alkane Properties and Environmental
Hazards: A Closer Look
• Due to the solubility and density of alkanes, oil spills into
the ocean or other bodies of water can have devastating
environmental consequences.
• The oil cannot dissolve or mix with the water, and
because it is less dense than water, it floats on top of
the surface of the water creating an oil slick, as depicted
in Figure .
• Since the oil slick remains at the surface of the water,
the organisms most affected by oil slicks are those
found on the surface of the ocean or near the
shorelines, including sea otters and seabirds.
• The chemical constituents of the oil are toxic though
ingestion, inhalation, and through skin and eye irritation.
Oil Spills. Crude oil coats the water’s surface in the
Gulf of Mexico
Classification of Carbon Bonds
• Carbon atoms participating in chemical bonds within a molecule can be classified
based on the number of carbon-carbon bonds that are formed.

• Primary carbon atom: one carbon neighbor

• Secondary carbon atom: two carbon neighbors
• Tertiary carbon atom: three carbon neighbors
• Quaternary carbon atom: four carbon neighbors

• The number of carbon neighbors that a carbon atom has can help determine the
reactivity of that carbon position.
• Thus, it is important to be able to recognize whether a carbon atom is primary,
secondary, tertiary, or quaternary in its structure.
Classification of carbon atoms as primary, secondary, tertiary, or quaternary

Classification of Carbon Atoms Within a Molecule

 Chemical Reactivity of Alkanes
As we know functional group contains a heteroatom or π bond and constitutes the reactive part of
a molecule. Alkanes are the only family of organic molecules that have no functional group, and
therefore, alkanes undergo few reactions.

• Alkanes contain strong carbon-carbon single bonds and strong carbon-hydrogen bonds. Both of
these bonds are nonpolar. Therefore, there is no portion of the molecule that carries any significant amount
of positive or negative charge, which is required for other ionic and polar molecules to be attracted to it.
Therefore alkanes generally do not react with ionic compounds such as most laboratory acids, bases,
oxidizing agents, or reducing agents. Consider butane as an example:

Neither positive ions nor negative ions are attracted to a nonpolar molecule. In fact, alkanes are
inert to reaction unless forcing conditions are used. Alkanes undergo so few reactions that they are
sometimes called paraffins, from the Latin parum affinis, meaning “little affinity.”
Types of Reactions
• Alkanes have very little reactivity and only
undergo three major types of reactions, including
the following:
✓ Combustion Reactions – burn them – destroying
the entire molecule. Combustion is an
oxidation–reduction reaction.
✓ Halogenation Reactions (substitution type) –
react them with some of the halogens, breaking
the carbon-hydrogen bonds
✓ Cracking Reactions – use heat and/or a catalyst
to crack alkanes, breaking carbon-carbon bonds.
Combustion:
An Oxidation and Reduction Reaction

Oxidation and reduction are opposite processes. As in acid–base reactions, there are always two components in these
reactions. One component is oxidized and one is reduced.

To determine if an organic compound undergoes oxidation or reduction, we concentrate on the carbon atoms of the
starting material and product, and compare the relative number of C –H and C – Z bonds, where Z = an element more
electronegative than carbon (usually O, N, or X).

Oxidation and reduction are then defined in two complementary ways.

Oxidation and Reduction of a Carbon Compound

Figure illustrates the oxidation of CH4 by replacing C – H bonds with C – O bonds (from left to right).

The symbol [O] indicates oxidation. Because reduction is the reverse of oxidation, the molecules in Figure
are progressively reduced moving from right to left, from CO2 to CH4.

The symbol [H] indicates reduction.

Problem
• Determine whether the organic compound is oxidized or reduced in each transformation.
Combustion Reactions
• The combustion of carbon compounds, especially hydrocarbons, has
been the most important source of heat energy for human civilizations
throughout recorded history.
• The practical importance of this reaction cannot be denied, but the
massive and uncontrolled chemical changes that take place in
combustion make it difficult to deduce mechanistic paths.
• Using the combustion of propane as an example, we see from the
following equation that every covalent bond in the reactants has been
broken and an entirely new set of covalent bonds have formed in the
products.
• No other common reaction involves such a profound and pervasive
change, and the mechanism of combustion is so complex that
chemists are just beginning to explore and understand some of its
elementary features.
CH3CH2CH3 + 5O2 → 3CO2 + 4H2O + heat
 • Atoms bond together to form compounds because in doing so
they attain lower energies than they possess as individual
atoms.

• When atoms combine to make a compound, energy is always

given off, and the compound has a lower overall energy.

Bond • When a chemical reaction occurs, molecular bonds are broken

and other bonds are formed to make different molecules. For

Energies
example, the bonds of two water molecules are broken to form
hydrogen and oxygen.
2H2O → 2H2 + O2
• Energy is always required to break a bond, which is known as
the bond energy. While the concept may seem simple, bond
energy serves a very important purpose in describing the
structure and characteristics of a molecule.
 Key Takeaways
• Energy is always required to break a bond.
• Energy is always released when a bond is made.
Although each molecule has its
own characteristic bond energy,
some generalizations are possible.

For example, although the exact value

of a C–H bond energy depends on the
particular molecule,
all C–H bonds have a bond energy of
roughly the same value because they
are all C–H bonds.
It takes roughly 100 kcal of energy to
break 1 mol of C–H bonds, so we
speak of the bond energy of a C–H
bond as being about 100 kcal/mol.

Table provides a list of average bond energies for common organic

bonds.
 • When a chemical reaction occurs, the atoms in the
reactants rearrange their chemical bonds to make
products. The new arrangement of bonds does not
have the same total energy as the bonds in the
reactants.
Heat of the • Therefore, when chemical reactions occur, there will
always be an accompanying energy change. The
reaction energy change of a reaction or the heat of the
reaction is called enthalpy.
(enthalpy) • It is represented by the mathematical symbol, ΔH,
and is calculated as the difference of the energy
required to break the bonds of the reactants minus
the energy released by the formation of the bonds
in the products.
• ΔH = Energy of Reactants – Energy of Products
Reaction Enthalpy
Exothermic Reactions. For an exothermic chemical reaction, energy is
given off as reactants are converted to products.

Endothermic Reactions. For an endothermic chemical reaction, energy

is absorbed as reactants are converted to products.
Exothermic and endothermic reactions can be thought of as having
energy as either a “product” of the reaction or a “reactant”, respectively.
Exothermic reactions release energy, so energy is a product.
Endothermic reactions require energy, so energy is a reactant.
Exothermic reactions will have a negative overall enthalpy and
endothermic reactions will have a positive overall enthalpy.
ΔH = Energy of Reactants – Energy of Products
Complete Combustion
• Complete combustion (given sufficient oxygen) of any hydrocarbon produces carbon dioxide (CO2) and water
(H2O).

• Example : Propane Combustion: C3H8 + 5O2 → 3CO2 + 4H2O

• The hydrocarbons become harder to ignite as the molecules get bigger. This is because the bigger molecules
don’t vaporize so easily – the reaction is much better if the oxygen and the hydrocarbon are well mixed as
gases.
• If the liquid is not very volatile, only those molecules on the surface can react with the oxygen. Bigger molecules
have greater Van der Waals attractions which makes it more difficult for them to break away from their neighbors
and turn to a gas.
• Provided the combustion is complete, all the hydrocarbons will burn with a blue flame. However, combustion
tends to be less complete as the number of carbon atoms in the molecules rises. That means that the bigger the
hydrocarbon, the more likely we are to get a yellow, smoky flame.
Incomplete Combustion
• Incomplete combustion (where there is not enough oxygen present) can lead to the
formation of carbon or carbon monoxide.

• As a simple way of thinking about it, the hydrogen in the hydrocarbon gets the first
chance at the oxygen to form water in the product, and the carbon gets whatever is
left over!

• When only carbon is formed, the presence of glowing carbon particles in a flame
turns it yellow, and black carbon is often visible in the smoke.

• If some oxygen can interact with the carbon, but not enough to form carbon dioxide
(CO2), then carbon monoxide (CO) is produced as a colorless poisonous gas.
Why carbon monoxide is poisonous?
• Oxygen is carried around the blood by hemoglobin, a protein found in red
blood cells.
• Carbon dioxide also binds with hemoglobin. Hemoglobin carries oxygen
from our lungs to every cell in our body, where it drops off the oxygen and
picks up carbon dioxide and carries it back to the lungs.
• Hemoglobin will then exchange the carbon dioxide for the oxygen in the air
that we breath in. When we exhale, we release the carbon dioxide.
• Carbon monoxide can also bind to hemoglobin. The difference is that
carbon monoxide binds irreversibly (or very strongly) – making that
particular molecule of hemoglobin useless for carrying oxygen. If we
breath in enough carbon monoxide we can die from an internal form of
suffocation!
Heat of Combustion
• The heat of combustion, ΔHc , is defined as the total energy released as heat when a
substance undergoes complete combustion with oxygen under a set of standard
conditions.
• It is calculated the same way that enthalpy is calculated, however, it is specific for a set of
standard conditions.
• Heat of Combustion is a useful value because it is a constant value for the type of material
being burned and can be used to compare the efficiency and utility of different fuel
sources used most often in society (oil, gasoline, natural gas, diesel, coal, wood, hydrogen,
ethanol, etc).
• In the United States, heating ratings are commonly given in British Thermal Units (BTU)
per pound of material. A common conversion to the metric units is:
BTU/lb = (kJ/kg)*2.326
• Heat of combustion, ΔHc, values common fuel sources and their associated CO2
emissions are indicated in Table.
Heat of
Combustion and
CO2 Emissions
Profile of
Common Fuels
 Petroleum
• Petroleum (from Greek: petra: “rock” + oleum: “oil”)
is a naturally occurring, yellow-to-black liquid
found in geological formations beneath the
Earth’s surface, which is commonly refined into
various types of fuels.
• It consists mainly of alkanes, cycloalkanes, and
alkenes of various lengths and some additional
minor organic compounds.
• Alkanes with five or more carbons are liquids
and are found as common components of
petroleum (also called crude oil).
• Many cycloalkanes are also found in petroleum
products as well including, gasoline, kerosene,
diesel, motor oil and many other heavy oils.
• Natural gas, on the other hand, is composed
predominantly of methane (CH4), but also
contains ethane (C2H6), propane (C3H8), and
butane (C4H10). Natural gas also contains trace
levels of nitrogen, carbon dioxide (CO2), and
hydrogen sulfide (H2S).
• Components of petroleum are separated by size using a
technique called fractional distillation.
• The resulting samples include gasoline with alkanes ranging
from five to ten carbons in length and kerosene with a mixture
of alkanes ranging in carbon length from ten to seventeen.
• Alkanes with longer carbon chains are found in diesel fuel, fuel
oil, petroleum jelly, paraffin wax, motor oils, and the very
highest chain length are used in asphalt.
• It is estimated that the world uses about 95 million barrels of
oil each day!
• The Environmental Protection Agency estimates that each
barrel of oil produces 0.43 metric tons of CO2.
• Note that a metric ton is equivalent to 1,000 kg. That means
that 40,850,000 metric tons of CO2 or 40,850,000,000 kg of
CO2 are released into the atmosphere each day just from oil
consumption!
• That is almost 15 billion metric tons of CO2 per year!
This calculation only includes the consumption of crude oil
and not other common fuel sources, such as natural gas, coal,
wood, and renewable energy sources like ethanol and
biodiesel.
Halogenation Reactions
(Substitution Type)

• In the presence of heat or light, alkanes can react with

halogens to form alkyl halides (or haloalkanes). This type
of reaction is called a substitution reaction, because the
halogen atom is taking the place of (or substituting
for) one of the hydrogen atoms on the alkane structure. It
should be noted that not all of the halogens react in the
same way with alkanes.
• The reaction between alkanes and fluorine: This
reaction is explosive even in the cold and dark, and you tend
to get carbon and hydrogen fluoride produced, rather than
the desired substitution reaction. It is of no particular interest
to organic chemists, as the reaction can be very dangerous,
and it does not yield the desired product. For example, the
desired product would be the alkyl fluoride:
• The reaction between alkanes and iodine: Iodine does not react
with the alkanes to any extent – at least, under normal lab conditions.
So this reaction is not useful either.

• The reactions between alkanes and chlorine or

bromine: There is no reaction in the dark, but if light and heat are
present, the reaction will produce the desired alkyl halides. Thus, we
will focus our discussion on halogenation reactions with chlorine and
bromine.
The Reaction of Methane and
Chlorine
• In the presence of a flame, the reactions are rather like the fluorine one –
producing a mixture of carbon and the hydrogen halide.
• The violence of the reaction drops considerably as we go from fluorine to
chlorine to bromine.
• The interesting reactions happen in the presence of ultra-violet light (sunlight
will do). These are photochemical reactions that happen at room temperature.
• We’ll look at the reactions with chlorine, although the reactions with bromine are
similar, but evolve more slowly.
• In the substitution reaction, a hydrogen atom in the methane is replaced by a
chlorine atom. This can happen multiple times, until all the hydrogens are
replaced.
• Ultimately, the longer the reaction proceeds, the more hydrogens in the alkane
are replaced.
• Thus, we end up with a mixture of chloromethane (CH3Cl), dichloromethane
(CH2Cl2), trichloromethane (CHCl3) and tetrachloromethane (CCl4).
The Reaction of The original mixture of a colorless gas (CH4) and a green gas
(Cl2) would produce steamy fumes of hydrogen chloride (HCl) and
Methane and a mist of organic liquids (mixture of the chlorinated methane).
All of the organic products are liquid at room temperature with
Chlorine the exception of the chloromethane (CH3Cl) which is a gas.
 Radical Reaction-Initiation

• This substitution reaction is an example

of a radical reaction, where only one
electron is transferred at a time.
• The heat or light, initiates the reaction by
breaking the bond between the two Cl
atoms in the chloride ion.
• This forms two radicals. A radical is an
atom, molecule, or ion that has unpaired
valence electrons.
• Thus, they are very unstable and
reactive.
• In the diagram, the first step of the
halogenation reaction is shown
below. This is termed initiation.
 Propagation and Termination Reactions
• Once the radical is initiated, it will attack the
alkane, in this case methane (CH4), and
create a new carbon radical. This stage of
the reaction is termed propagation, as one
radical species creates, or propagates,
another radical.

The final stage of a radical reaction is

the termination reaction which quenches
the radical species present. For the
methane – chlorine reaction this is the
formation of the chloromethane (CH3Cl).
• In summary, radical reactions occur in three stages:
• Initiation – where a radical species is generated, generally
by heat, light, or other catalytic process.

• Propagation – where one radical species interacts with

another molecule to create another radical species.

• Termination – where two radical species interact and

quench the radical reaction an form a stable product.
Larger Alkanes and Chlorine
• As seen with the methane example, if halogenated
larger alkanes, we would again get a mixture of
substitution products, but it is worth just looking
briefly at what happens if only one of the hydrogen
atoms gets substituted (monosubstitution) – just to
show that things aren’t always as straightforward
as they seem!
• For example, with propane, we could get one of
two isomers:
If chance was the only factor, we would expect to get three times
as much of the isomer with the chlorine on the end.

There are 6 hydrogens that could get replaced on the end carbon
atoms compared with only 2 in the middle.

In fact, we get about the same amount of each of the two isomers.
If we use bromine instead of chlorine, the great
majority of the product is where the bromine is
attached to the center carbon atom. Why does
this happen?

It has to do with the stability of the carbon radical

intermediate that forms during the reaction.
Carbons that have more carbon neighbors will more easily
lose a hydrogen and form a carbon radical intermediate.
The neighboring carbons, being larger than the neighboring
hydrogen atoms, can help stabilize the formation of the
carbon radical.
Thus, in the halogenation reaction tertiary carbons will be
the most reactive positions, followed by secondary carbons
and finally primary carbons.
Quaternary carbons are unreactive as they do not have any
hydrogens available that can be substituted by a halogen.
 Halogenation Reactions with Cycloalkanes

• The reactions of the cycloalkanes are generally just the same as the alkanes,
with hydrogen atoms on the cyclic ring structure being replaced by the
halogen atom. For example in the presence of UV light, cyclopropane will
undergo substitution reactions with chlorine or bromine just like a non-cyclic
alkane.

However, the small ring structures – particularly cyclopropane – also have the ability to react
in the dark. In the absence of UV light, cyclopropane can undergo addition reactions in which
the ring is broken. For example, with bromine, cyclopropane gives following linear compound.

This can still happen in the presence of UV light – but you will get a mixture of the substitution
reactions as well. The ring is broken because cyclopropane suffers badly from ring strain. Recall that
the bond angles in the ring are 60° rather than the normal value of about 109.5° when the carbon
makes four single bonds.
Health: Halogenated Hydrocarbons
• Once widely used in consumer products, many chlorinated hydrocarbons are suspected
carcinogens (cancer-causing substances) and also are known to cause severe liver
damage.
• An example is carbon tetrachloride (CCl4), once used as a dry-cleaning solvent and in fire
extinguishers but no longer recommended for either use.
• Even in small amounts, its vapor can cause serious illness if exposure is prolonged.
• Moreover, it reacts with water at high temperatures to form deadly phosgene (COCl2) gas,
which makes the use of CCl4 in fire extinguishers particularly dangerous.
• Ethyl chloride, in contrast, is used as an external local anesthetic. When sprayed on the
skin, it evaporates quickly, cooling the area enough to make it insensitive to pain. It can
also be used as an emergency general anesthetic.
• Bromine-containing compounds are widely used in fire extinguishers and as fire
retardants on clothing and other materials. Because they too are toxic and have adverse
effects on the environment, scientists are engaged in designing safer substitutes for them,
as for many other halogenated compounds.
Health: Chlorofluorocarbons and the
Ozone Layer
• Alkanes substituted with both fluorine (F) and chlorine (Cl) atoms have been used as the
dispersing gases in aerosol cans, as foaming agents for plastics, and as refrigerants.
• Chlorofluorocarbons contribute to the greenhouse effect in the lower atmosphere.
• They also diffuse into the stratosphere, where they are broken down by ultraviolet (UV)
radiation to release Cl atoms. These in turn break down the ozone (O3) molecules that
protect Earth from harmful UV radiation.
• Worldwide action has reduced the use of CFCs and related compounds. The CFCs and
other Cl- or bromine (Br)-containing ozone-destroying compounds are being replaced with
more benign substances.
• Hydrofluorocarbons (HFCs), such as CH2FCF3, which have no Cl or Br to form radicals, are
one alternative.
• Another is hydrochlorofluorocarbons (HCFCs), such as CHCl2CF3. HCFC molecules break
down more readily in the troposphere, and fewer ozone-destroying molecules reach the
stratosphere.
Ozone Depletion in the
Upper Atmosphere
Ozone in the upper atmosphere shields Earth’s surface
from UV radiation from the sun, which can cause skin
cancer in humans and is also harmful to other animals
and to some plants. Ozone “holes” in the upper
atmosphere (the gray, pink, and purple areas at the
center) are large areas of substantial ozone depletion.
They occur mainly over Antarctica from late August
through early October and fill in about mid-November.
Ozone depletion has also been noted over the Arctic
regions. The largest ozone hole ever observed occurred
on 24 September 2006.

Source: Image courtesy of NASA

Cracking Alkanes
• Cracking is the name given to breaking up large hydrocarbon
molecules into smaller and more useful bits.
•
• This is achieved by using high pressures and temperatures without
a catalyst, or lower temperatures and pressures in the presence of
a catalyst.

• A catalyst is a substance that increases the rate of a chemical reaction

without itself undergoing any permanent chemical change.
• The source of the large hydrocarbon molecules is often the naphtha fraction or the gas
oil fraction from the fractional distillation of crude oil (petroleum).

• These fractions are obtained from the distillation process as liquids, but are re-vaporized
into the gaseous phase before cracking.

• There isn’t any single unique reaction happening in the cracker. The hydrocarbon
molecules are broken up in a fairly random way to produce mixtures of smaller
hydrocarbons, some of which have carbon-carbon double bonds.

• One possible reaction involving the hydrocarbon C15H32 might be:

C15H32 → 2C2H4 + C3H6 + C8H18
• Or, showing more clearly what happens to the various atoms and bonds:

This is only one way in which this particular molecule might break up. Notice that in addition to
producing smaller alkanes, the cracking reaction can also produce alkenes with double bonds.
In this case, the alkenes – ethene (C2H4) and propene (C3H6) – are important materials for
making plastics or producing other organic chemicals. The octane is one of the molecules
found in petrol (gasoline).
Looking Closer: An Alkane Basis for
Properties of Other Compounds
• An understanding of the physical properties of the alkanes is important in that
petroleum and natural gas and the many products derived from them—gasoline,
bottled gas, solvents, plastics, and more—are composed primarily of alkanes.

• This understanding is also vital because it is the basis for describing the properties of
other organic and biological compound families.

• For example, large portions of the structures of lipids consist of nonpolar alkyl
groups.

• Lipids include the dietary fats and fatlike compounds called phospholipids and
sphingolipids that serve as structural components of living tissues.
Lipids have both polar and nonpolar groups, enabling them to bridge the gap between water-
soluble and water-insoluble phases. This characteristic is essential for the selective
permeability of cell membranes.

Comparision of Lipids and

Alkanes. Tripalmitin (a), a typical fat
molecule, has long hydrocarbon chains
typical of most lipids. Compare these
chains to hexadecane (b), an alkane
with 16 carbon atoms.