HYDROCARBONS

The simplest organic compounds are hydrocarbons, which contain only the elements carbon and hydrogen. How many
different compounds do you think two elements can form? You might guess that only a few compounds are possible. However,
thousands of hydrocarbons are known, each containing only the elements carbon and hydrogen. The simplest hydrocarbon
molecule CH4 consists of a carbon atom bonded to form hydrogen atoms called methane.
 Alkanes- hydrocarbons that have only single bonds
 Alkenes- hydrocarbons that have double bonds
 Alkynes- hydrocarbons that have triple bonds

Bonding
 Atoms can become bonded with each other, and their electronic structure governs the type of bond
formed. The main two types of bonds that are formed are called ionic and covalent.

Ionic Bond
 Ionic bonding is important between atoms of vastly different electronegativity. The bond results from
one atom giving up an electron while another atom accepts the electron. Both atoms attain a stable nobel
gas configuration.
 In the compound lithium fluoride, the 2s1 electron of lithium is transferred to the 2p5 orbital of fluorine.
The lithium atom gives up an electron to form the positively charged lithium cation with 1s2, 2s0
configuration, and the fluorine atom receives an electron to form a fluoride anion with 1s2, 2s2, 2p6
configuration.
 Thus the outer energy levels of both ions are completely filled. The ions are held together by the
electrostatic attraction of the positive and negative ions.

Covalent Bond
 A covalent bond is formed by a sharing of two electrons by two atoms.
 A hydrogen atom possessing the 1s1 electron joins with another hydrogen atom with its 1s1
configuration. The two atoms form a covalent bond with two electrons by sharing their electrons.

In hydrogen fluoride, HF, the hydrogen 1s electron is shared with a 2p5 electron in fluorine (1s2, 2s2,
2p5), and the molecule is now held together by a covalent bond. In this case, the fluorine atom is much more
electronegative than the hydrogen atom and the electrons in the bond tend to stay closer to the fluorine atom.
This is called a polar covalent bond, and the atoms possess a small partial charge denoted by the Greek d
symbol.
Homologous series/compounds
related compounds that have the same functional group (groups of atoms found within molecules that are involved
in the chemical reactions characteristic of those molecules)

CnH2n+2 (alkanes) or CnH2n (alkenes) CnH2n-2 (alkynes)

EMPIRICAL FORMULA
simplest ratio of atoms in a molecule

MOLECULAR FORMULA
actual numbers of atoms in a
molecule

structural formula
 unambiguously shows how the atoms are bonded together
 can use condensed structural formulas
◦ bonds are omitted, repeated groups put together, side chains put in brackets

CH CH CH CH CH CH or even CH (CH ) CH
3 2 2 2 2 3 3 2 4 3
-CH CH(CH )CH
3 3 3

Skeletal Formula
 not accepted for answers but often used in questions
 every “corner” represents a carbon
 hydrogens are implied
Isomers
 (structural) isomers: compounds with the same molecular formula but different structure (arrangement of atoms)
 different isomers are completely different compounds
 have different physical properties such as melting point and boiling point

Writing Structural
Formulas

You will be writing structural formulas throughout this course. Perhaps a few hints about how to do so will
be helpful. Let’s look at another case of isomerism. Suppose we want to write out all possible structural
formulas that correspond to the molecular formula C5H12. We begin by writing all five carbons in a
continuous chain.

This chain uses up one valence for each of the end carbons and two valences for the carbons in the middle
of the chain. Each end carbon therefore has three valences left for bonds to hydrogens. Each middle carbon
has only two valences for bonds to hydrogens. As a consequence, the structural formula in this case is
written as:
To find structural formulas for the other isomers, we must consider branched chains. For example, we can
reduce the longest chain to only four carbons and connect the fifth carbon to one of the middle carbons, as
in the following structural formula:

If we add the remaining bonds so that each carbon has a valence of 4, we see that three of the carbons have
three hydrogens attached, but the other carbons have only one or two hydrogens. The molecular formula,
however, is still C5H12.

Suppose we keep the chain of four carbons and try to connect the fifth carbon somewhere else. Consider
the following chains:

Do we have anything new here? No! The first two structures have five-carbon chains, exactly as in the
formula for pentane, and the third structure is identical to the branched chain we have already drawn for 2-
methylbutane—a four-carbon chain with a one-carbon branch attached to the second carbon in the chain
(counting now from the right instead of from the left). Notice that for every drawing of pentane, you can
draw a line through all five carbon atoms without lifting your pencil from the paper.
For every drawing of 2-methylbutane, a continuous line can be drawn through exactly four carbon atoms.
But there is a third isomer of C5H12. We can find it by reducing the longest chain to only three carbons and
connecting two one-carbon branches to the middle carbon.

If we fill in the hydrogens, we see that the middle carbon has no hydrogens attached to it.

So we can draw three (and only three) different structural formulas that correspond to the molecular
formula C5H12, and in fact, we find that only three different chemical substances with this formula exist.
They are commonly called n-pentane (n for normal, with an unbranched carbon chain), isopentane, and
neopentane.
Abbreviated Structural Formulas
Structural formulas like the ones we have written so far are useful, but they are also somewhat cumbersome.
They take up a lot of space and are tiresome to write out. Consequently, we often take some shortcuts that
still convey the meaning of structural formulas. For example, we may abbreviate the structural formula of
ethanol (ethyl alcohol) from:

Each formula clearly represents ethanol rather than its isomer methoxymethane (dimethyl ether), which can
be represented by any of the following structures:

The structural formulas for the three pentanes can be abbreviated in a similar fashion.

Sometimes these formulas are abbreviated even further. For example, they can be printed on a single line
in the following ways:

EXAMPLE 1.11
Write a structural formula that shows all bonds for each of the following:
a. CH3CCl2CH3 b. (CH3)2C(CH2CH3)2
Solution

Perhaps the ultimate abbreviation of structures is the use of lines to represent the carbon framework:

In these formulas, each line segment is understood to have a carbon atom at each end. The hydrogens are
omitted, but we can quickly find the number of hydrogens on each carbon by subtracting from four (the
valence of carbon) the number of line segments that emanates from any point. Multiple bonds are
represented by multiple line segments. For example, the hydrocarbon with a chain of five carbon atoms and
a double bond between the second and third carbon atoms (that is, CH3CH =CHCH2CH3) is represented as
follows: