ORGANIC CHEMISTRY IN THE MODERN ERA

DEC 17, 2021

INTRODUCTION

Hydrocarbons are organic compounds that are entirely made up of only two kinds of atoms – carbon
and hydrogen. Typically, hydrocarbons are colourless gases that have very weak odours.
Hydrocarbons can feature simple or relatively complex structures and can be generally classified
into four subcategories, namely alkanes, alkenes, alkynes, and aromatic hydrocarbons.The study of
hydrocarbons can provide insight into the chemical properties of other functional groups and their
preparation. Furthermore, hydrocarbons such as propane and butane are used for commercial fuel
purposes in the form of Liquefied Petroleum Gas (LPG). Benzene, one of the simplest aromatic
hydrocarbons, serves as raw material for the synthesis of many synthetic drugs. The molecular
formula for these compounds is CxHy. The existence of hydrocarbons is seen in plants and trees.
For example, Carotenes is an organic pigment which is found in green leaves and carrots. These
hydrocarbons make up to 98% of natural crude rubber. Further, they possess large internal energy
which renders them their importance.

A hydrocarbon is a molecule whose structure includes only hydrogen and carbon atoms.
Hydrocarbons form bonds with other atoms in order to create organic compounds.

Hydrocarbon derivatives are based on simple hydrocarbon compounds that contain only hydrogens
and carbons.

Hydrocarbon derivatives contain at least one element other than hydrogen or carbon, such as
oxygen, nitrogen or one of the halogen atoms (elements in column 7A of the Periodic Table).

A hydrocarbon is an organic compound made of nothing more than carbons and hydrogens. It is
possible for double or triple bonds to form between carbon atoms and even for structures, such as
rings, to form.
Saturated hydrocarbons have as many hydrogen atoms as possible attached to every carbon. For
carbons on the end of a molecular chain, three can be attached. For carbons in the middle of a
chain or a ring, two can be attached. For a carbon atom all by itself, four hydrogen atoms can be
attached. Saturated hydrocarbons have only single bonds between adjacent carbon atoms.
Unsaturated hydrocarbons have double and/or triple bonds between some of the carbon atoms.

BODY
Compounds that are made up of carbon and hydrogen atoms with a specific group of atoms
attached are called hydrocarbon derivatives. Learn more about the definition of hydrocarbon
derivatives, their comparison to simple hydrocarbons and their properties such as electronegativity
and polarity.
What Are Hydrocarbon Derivatives?
Can you imagine life without a refrigerator? Thanks to hydrocarbon derivatives, you don't have to. In
the early 1900s, refrigeration technology evolved from chunks of ice to machine powered and
chemically cooled systems. And for more than fifty years, the best chemicals for the job were
chlorofluorocarbons, or CFCs, made of chlorine atoms, fluorine atoms and carbon atoms.

Unfortunately for the planet, CFCs are intensely damaging to the ozone layer, which is the layer of
O3 molecules high in the atmosphere that protect Earth from powerful ultraviolet rays. A chlorine
atom within a single CFC has the power to damage one hundred thousand molecules of ozone
before it breaks down. CFCs are still present as refrigerants and aerosols, but luckily the use of
them is decreasing.

Let's compare the structure of a simple CFC with an equally simple hydrocarbon and see if we can
figure out what a hydrocarbon derivative is.

As you may recall, a hydrocarbon is a compound made mostly of hydrogen and carbon atoms
bonded together through the sharing of electrons. Some classic examples include methane, ethene
and benzene. The simplest hydrocarbon, methane, consists of one central carbon atom with four
hydrogens bonded to it.

One of the simple CFCs, Freon 12, consists of one central carbon atom with two chlorines and two
fluorines bonded to it. What similarities do you notice between the two?

In each case, there is a central carbon atom and four bonds extending out if it.

What differences do you notice? Maybe that methane only contains hydrogens and a carbon, while
Freon contains chlorine atoms, fluorine atoms and a carbon?
How about comparing methane to another hydrocarbon derivative: methanol? Methanol has a
central carbon bonded to three hydrogens and one oxygen. The oxygen is, in turn, bonded to a
hydrogen.

Again, there is a central carbon that has four bonds extending from it.

Notice any patterns yet? Carbons are the central atoms in both cases. A hydrocarbon consists of
carbons and hydrogens. Hydrocarbon derivatives contain different elements attached to the carbon
instead of only hydrogen.

Perhaps you've had to look up derivatives of Latin words in the English language, or take the
derivative of a curved line in calculus. A derivative is something that is based on another source. In
our case, hydrocarbon derivatives are based on simple hydrocarbon compounds that contain only
hydrogens and carbons.

Hydrocarbon derivatives contain at least one element other than hydrogen or carbon, such as
oxygen, nitrogen or one of the halogen atoms (elements in column 7A).

Most of the time, the atoms present in a hydrocarbon derivative are attached as part of a distinct
group. These groups are known as functional groups because they affect how the compound
behaves. Sometimes functional groups affect physical properties of a compound as well.

Examples of functional groups include alcohols, aldehydes, ketones, amines and esters.

Complex hydrocarbons and their derivatives are found throughout nature. Natural rubber, for
example, is a hydrocarbon that contains long chains of alternating C=C double bonds and C C
single bonds.

Writing the structure of complex hydrocarbons can be simplified by using a line notation in which a
carbon atom is assumed to be present wherever a pair of lines intersect and enough hydrogen
atoms are present to satisfy the tendency of carbon to form a total of four bonds.
There are a variety of techniques for isolating both pleasant and foul-smelling compounds known
as essential oils from natural sources, particularly from plants. These compounds are not
"essential," in the sense of being vital to life. They were given that name because they give off a
distinct "essence," or smell.

The essential oils are used in perfumes and medicines. Some of these compounds can be isolated
by gently heating, or steam distilling, the crushed flowers of plants. Others can be extracted into
nonpolar solvents, or absorbed onto grease-coated cloths in which the plants are wrapped. Many of
these essential oils belong to classes of compounds known as terpenes and terpenoids. The
terpenes are hydrocarbons that usually contain one or more C=C double bonds. The terpenoids are
oxygen-containing analogs of the terpenes.

Examples of terpenes include -pinene and -pinene, the primary components of turpentine that give
rise to its characteristic odor.

Camphor and menthol are examples of terpenoids.

Both of these compounds have a fragrant, penetrating odor and taste cool. Camphor is used as a
moth repellent. Menthol is a mild anesthetic that is added to some brands of cigarettes. The
terpenoids also include compounds such as geranial and neral, a pair of cis/trans stereoisomers that
can be found in lemon oil. Geranial has a strong lemon odor. Neral tastes sweeter, but has a less
intense odor.
Although the terpenes and terpenoids discussed so far have very different structures, they have one
important property in common: They all contain 10 carbon atoms, neither more nor less. Each of
these compounds can be traced back to a reaction in which a pair of five-carbon molecules are
fused. Thus, it isn't surprising that we can also find sesquiterpenes (15 carbon atoms), diterpenes
(20 carbon), triterpenes (30 carbons), and so on. Important examples of these compounds include
Vitamin A and the b-carotene that gives carrots their characteristic color.

Steroids aren't terpenes or terpenoids in the literal sense because they don't contain the
characteristic number of carbon atoms. Consider cholesterol, for example, which is one of the most
important steroids.
Analysis of this structure suggests the formula C27H46O, which doesn't fit the pattern expected of a

terpenoid. The biosynthetic precursor of this molecule, however, is a 30-carbon triterpene that is
converted into cholesterol by a series of enzyme-catalyzed reactions.

By definition, the steroids are compounds that have the basic structure formed by fusing three six-
membered rings and a five-membered ring. The most important property of this molecule is the fact
that, with the exception of the -OH group on the lower-left-hand corner of the molecule, there is
nothing about the structure of this compound that would make it soluble in water.

In this day of cholesterol-free products, it is useful to recognize that it is absurd to label products
such as peanut butter as cholesterol-free. That is like saying that the Sahara desert is rain-free.
Peanut butter is made from peanuts and cholesterol isn't a characteristic ingredient in plants; it is
synthesized by animals, particularly mammals. It is also useful to note that placing someone on a
cholesterol-free diet won't reduce their cholesterol level to zero. Even on a low-cholesterol diet, the
individual will synthesize about 0.80 grams of cholesterol per day. The key question is: Is there
excess of cholesterol in the blood stream? If there is, a diet that reduces the intake of cholesterol
might be important.

Cholesterol is the biosynthetic precursor for the synthesis of all of the major classes of hormones,
the chemical messengers that coordinate the activity of different cells in a multicellular organism.
The steroid hormones include the progestogens, estrogens, and androgens.

Progesterone is an example of a progestogen. This hormone plays a vital role in pregnancy. After
ovulation, the corpus luteum secretes progesterone, which prepares the lining of the uterus for
implantation of the fertilized ovum. Progesterone is then released by the placenta throughout
pregnancy to suppress ovulation. Progesterone was therefore the model on which the first oral
contraceptives were built. Progesterone itself is not a good oral contraceptive because this hormone
is degraded in the digestive system. It therefore requires massive doses of progesterone to prevent
pregnancy when this hormone is taken orally.
The estrogen hormones, such as estrone and estradiol serve three functions. First, they are
responsible for the development of the secondary sex characteristics that appear at the onset of
puberty in women. Second, they participate in both the ovarian and estrus cycles, and are therefore
another model for the design of oral contraceptives. Third, they stimulate the development of the
mammary glands during pregnancy.

The androgen hormones, such as androsterone and testosterone play an equivalent role in men,
where they are responsible for the secondary sex characteristics that appear at puberty.
Testosterone is the true male sex hormone; androsterone is a metabolized form of this steroid that is
excreted in the urine.

The Aromatic Hydrocarbons and Their Derivatives

At the turn of the 19th century, one of the signs of living the good life was having gas lines
connected to your house, so that you could use gas lanterns to light the house after dark. The gas
burned in these lanterns was called coal gas because it was produced by heating coal in the
absence of air. The principal component of coal gas was methane, CH 4.

In 1825, Michael Faraday was asked to analyze an oily liquid with a distinct odor that collected in
tanks used to store coal gas at high pressures. Faraday found that this compound had the empirical
formula: CH. Ten years later, Eilhardt Mitscherlich produced the same material by heating benzoic
acid with lime. Mitscherlich named this substance benzin, which became benzene when translated
into English. He also determined that the molecular formula of this compound is C 6H6.
Benzene is obviously an unsaturated hydrocarbon because it has far less hydrogen than the
equivalent saturated hydrocarbon: C6H14. But benzene is too stable to be an alkene or alkyne.

Alkenes and alkynes rapidly add Br2 to the C=C or CC bonds, whereas benzene only reacts with

bromine in the presence of a catalyst: FeBr3. Furthermore, when benzene reacts with Br2 in the

presence of FeBr3, the product of this reaction is a compound in which a bromine atom has

been substituted for a hydrogen atom, not added to the compound the way an alkene adds bromine.

FeBr3
C6H6 + C6H5Br +
Br2 HBr
Other compounds were eventually isolated from coal that had similar properties. Their formulas
suggested the presence of multiple C=C bonds, but these compounds were not reactive enough to
be alkenes. Because they often had a distinct odor, or aroma, they became known as aromatic
compounds.

The structure of benzene was a recurring problem throughout most of the 19th century. The first
step toward solving this problem was taken by Friedrich August Kekule in 1865. (Kekule's interest in
the structure of organic compounds may have resulted from the fact that he first enrolled at the
University of Giessen as a student of architecture.) One day, while dozing before a fire, Kekule
dreamed of long rows of atoms twisting in a snakelike motion until one of the snakes seized hold of
its own tail. This dream led Kekule to propose that benzene consists of a ring of six carbon atoms
with alternating C C single bonds and C=C double bonds. Because there are two ways in which
these bonds can alternate, Kekule proposed that benzene was a mixture of two compounds in
equilibrium.
Kekule's structure explained the formula of benzene, but it did not explain why benzene failed to
behave like an alkene. The unusual stability of benzene wasn't understood until the development of
the theory of resonance. This theory states that molecules for which two or more satisfactory Lewis
structures can be drawn are an average, or hybrid, of these structures. Benzene, for example, is a
resonance hybrid of the two Kekule structures.

The difference between the equilibrium and resonance descriptions of benzene is subtle, but
important. In the equilibrium approach, a pair of arrows is used to describe a reversible reaction, in
which the molecule on the left is converted into the one on the right, and vice versa. In the
resonance approach, a double-headed arrow is used to suggest that a benzene molecule does not
shift back and forth between two different structures; it is a hybrid mixture of these structures.

One way to probe the difference between Kekule's idea of an equilibrium between two structures
and the resonance theory in which benzene is a hybrid mixture of these structures would be to study
the lengths of the carbon-carbon bonds in benzene. If Kekule's idea was correct, we would expect to
find a molecule in which the bonds alternate between relatively long C C single bonds (0.154 nm)
and significantly shorter C=C double bonds (0.133 nm). When benzene is cooled until it crystallizes,
and the structure of the molecule is studied by x-ray diffraction, we find that the six carbon-carbon
bonds in this molecule are the same length (0.1395 nm). The crystal structure of benzene is
therefore more consistent with the resonance model of bonding in benzene than the original Kekule
structures.

The resonance theory does more than explain the structure of benzene it also explains why
benzene is less reactive than an alkene. The resonance theory assumes that molecules that are
hybrids of two or more Lewis structures are more stable than those that aren't. It is this extra stability
that makes benzene and other aromatic derivatives less reactive than normal alkenes. To
emphasize the difference between benzene and a simple alkene, many chemists replace the Kekule
structures for benzene and its derivatives with an aromatic ring in which the circle in the center of
the ring indicates that the electrons in the ring are delocalized; they are free to move around the
ring.

The significance of the circle in the center of this aromatic ring might best be understood by asking:
What is wrong with the Kekule structures for benzene? We start by building a sigma-bond skeleton

for the benzene ring in which each of the carbon atoms is sp2 hybridized. This leaves us with one
electron in a 2p orbital on each of the six carbon atoms.

If we assume that the interaction between the 2p orbitals is localized between a pair of carbon
atoms, we get one of the Kekule structures for benzene. Switching the pairs of atoms that form
bonds gives us the other Kekule structure.

But if we allow the six electrons in the six 2p orbitals to interact to form a set of molecular orbitals,
we can delocalize the electrons so that they are free to move from one carbon atom to another
around the ring.
It is this delocalization of electrons around the aromatic ring that is conveyed by the circle that is
often written inside the ring. It is also the delocalization of electrons that makes benzene less
reactive than a simple alkene.

Aromatic compounds were being extracted from coal tar as early as the 1830s. As a result, many of
these compounds were given common names that are still in use today. A few of these compounds
are shown below.

There are three ways in which a pair of substituents can be placed on an aromatic ring. In
the ortho (o) isomer, the substituents are in adjacent positions on the ring. In the meta (m) isomer,
they are separated by one carbon atom. In the para (p) isomer, they are on opposite ends of the
ring. The three isomers of dimethylbenzene, or xylene, are shown below.

CONCLUSION

Compounds that are made up of carbon and hydrogen atoms with a specific group of atoms
attached are called hydrocarbon derivatives. Learn more about the definition of hydrocarbon
derivatives, their comparison to simple hydrocarbons and their properties such as electronegativity
and polarity.
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Hydrocarbon Derivatives: Definition & Properties - Video & Lesson Transcript | Study.com

Hydrocarbons (purdue.edu)

Hydrocarbon toxicity: A review - PubMed (nih.gov)

Hydrocarbon Definition (investopedia.com)

Hydrocarbon and its derivatives (slideshare.net)