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Lab 01 Structure and Bonding
Lab 01 Structure and Bonding
Note: Every C has four bonds (lines) and every H only one.
C C C C C C
H H H H H H
H C C C C C C H
H H H H H H
Every carbon atom requires two H atoms except for the end carbon atoms,
which require three hydrogen atoms. If n is the number of carbon atoms in an
alkane, then 2n + 2 is the number of hydrogen atoms. The general formula for
any alkane is CnH2n + 2. How many H atoms are required for n = 5? Check your
answer in the table above.
Obtain a model kit and make a model of hexane. Carbon atoms are black
spheres and hydrogen atoms are yellow spheres. Why do the black spheres have
four holes and the yellow spheres only one hole? Look at your model. Does the
chain of carbon atoms lie in a straight line or in a zigzag pattern?
2 4 6
Cycloalkanes Join the two end carbons of your hexane model. The new
structure is a continuous loop or ring and is called cyclohexane. The prefix cyclo-
means the following number of carbons (hex- = six) is in a ring, and the suffix
ane means there are no multiple bonds in the ring compound. How does the
number of carbon atoms, n, compare in hexane and cyclohexane? Write a general
formula for cycloalkanes.__________ Three different bond-line depictions of
cyclohexane are shown below.
Sigma () and Pi () Bonds So far, all of the structures you have made
contain only single bonds. The first bond made between two carbon atoms is
called a bond and the second and third bonds are called bonds. The symbol
is the Greek sigma and is pi.
H
H H H
H C C H
H C C H CC
H H
H H
Tilt your model of methane so you can observe the angle made by the
carbon atom and any two hydrogen atoms. This is the tetrahedral angle, which
is 109.5o.
Tilt your model of ethene so you can observe the angle made by one
carbon atom and its two hydrogen atoms. This is the planar angle, which is
120o.
180o
Observe the angle made by any three atoms. This angle is the linear angle,
which is 180o.
Carbon A carbon atom is made up of protons, neutrons and electrons. The total
number of protons (6) equals the total number of electrons (6), so the atom is
neutral or uncharged. The protons and neutrons are concentrated in the nucleus
and do not participate in bonding. The 6 electrons are found outside the nucleus
in orbitals. Orbitals are three-dimensional spaces where electrons are found. The
electrons in the outermost main shell of carbon can take part in bonding with
other atoms; therefore, we are most interested in these electrons. Electrons in the
outermost main shell are called valence electrons. Carbon forms four bonds in
stable molecules. A carbon atom has four valence electrons, which are found in
four valence orbitals. When carbon atoms join to form molecules, some of the
orbitals may change shape (hybridize), but each carbon always has four orbitals.
Hybrid Orbitals Carbon can hybridize to make two hybrid orbitals, three hybrid
orbitals or four hybrid orbitals. Each bonded carbon atom will always have four
orbitals. As we shall see, these three kinds of hybridization are necessary for
carbon to make alkynes, alkenes and alkanes. Carbon always has four valence or
bonding orbitals. When carbon forms two hybrid orbitals, two orbitals remain
unhybridized. When carbon forms three hybrid orbitals, one orbital remains
unhybridized. When carbon forms four hybrid orbitals, no orbital remains
unhybridized. All hybrid orbitals are shaped like a teardrop. The following
graphic show a hybrid orbital.
A p orbital
An s orbital
Single Bonds Carbon-to-carbon single bonds form when two hybrid orbitals
overlap end-to-end. Each hybrid orbital contains one electron, so when the
orbitals merge, the two electrons are found in the three-dimensional space on a
straight line between the two atoms. Think of the hybrid orbitals themselves as
electrons. The electrons have opposite spins and hold the atoms together like tiny
magnets attracting each other. The following graphic depicts the end-to-end
overlap of two hybrid orbitals from two carbon atoms forming a single bond,
which is also a sigma bond. Each carbon has three other bonds that are indicated
by squiggly lines.
overlap
of hybrid
orbitals
Carbon to hydrogen single bonds form when a hybrid orbital of a carbon atom
overlaps with an s orbital from a hydrogen atom. The graphic below shows a
carbon atom forming one single (sigma) bond with hydrogen.
of hybrid
and s
orbitals
carbon hydrogen bond
Carbon-to-hydrogen single bond
overlap of hybrid
bond
orbitals ( bond)
and of p orbitals
( bond)
bond
carbon 1 carbon 2
Carbon-to-carbon double bond
The figure below show the potential surfaces of two p orbitals coming
together to form a bond. The underlying bond is not shown.
yz plane
Overlap of p orbitals
A triple bond
H H
H C C H
H H
ethane
Both carbon atoms are identical in ethane. One is shown in red for
discussion purposes. All four bonds to the red carbon are single () bonds. We
learned above that carbon always makes bonds from hybrid orbitals. Thus, four
hybrid orbitals are required by the red carbon to form four single bonds. When a
carbon atom has four hybrid orbitals, we call that carbon atom sp3 hybridized,
and we call each of its four hybrid orbitals sp3-hybrid orbitals. A principle of
valence-bond theory is that hybrid orbitals around a given carbon orient as far
away from each other as possible. Therefore, the four hybrid orbitals orient
toward the corners of a regular tetrahedron. Thus, we can determine the shape of
a carbon atom by its hybridization. The orbitals of an sp3-hybridized carbon are
tetrahedral and result in methane having a tetrahedral shape as shown above.
H H
C C
H H
ethene
The red carbon has four bonds and requires four orbitals, a p orbital for its
bond and three hybrid orbitals for its three bonds. A carbon atom with three
hybrid orbitals is called an sp2-hybridized carbon, and its three hybrid orbitals are
called sp2-hybrid orbitals. The three hybrid orbitals orient as far away from each
Alkynes Consider the structure of ethyne, which has the common name
acetylene.
H C C H
acetylene
The red carbon has four bonds and requires four orbitals, two p orbitals for
its two bonds and two hybrid orbitals for its two bonds. A carbon atom with
two hybrid orbitals is called an sp-hybridized carbon, and its two hybrid orbitals
are called sp-hybrid orbitals. The two hybrid orbitals orient as far away from each
other as possible, in a line 180o apart. The orientation of the hybrid orbitals
determines the shape around the carbon atom. The shape is linear. Both carbon
atoms of acetylene (ethyne) are sp hybridized. Therefore, the four atoms of
ethane are linear as seen above.
Summary: Carbon has four bonds, which may be or. The first bond made
by carbon is always a bond. The second bond of a double bond and the second
and third bonds of a triple bond are bonds. Carbon makes bonds with hybrid
orbitals and bonds with p orbitals. The number of bonds or hybrid orbitals
determines the shape around a carbon atom, because hybrid orbitals orient as far
apart as possible. An alkane carbon is sp3 hybridized, has four hybrid sp3 orbitals,
forms four bonds 109.5o apart and is tetrahedral. An alkene carbon is sp2
hybridized, has three hybrid sp2 orbitals, forms three bonds 120o apart plus
one bond and is planar. An alkyne carbon is sp hybridized, has two hybrid
orbitals, forms two bonds 180o apart plus two bonds and is linear.
Hexane has no branches. Next, consider the structure below. Like hexane,
it has six carbon atoms in its main or longest chain. However, it also has a branch
at C3.
Partial Structures If we start with methane, CH4, and remove one of its H atoms,
we have CH3. CH3 is an incomplete or partial structure because carbon has only
three bonds, and carbon always has four bonds in complete structures.
H H
take away one H
H C H H C
H H
methane methyl
The name suffix changes from -ane to -yl when one hydrogen atom is
removed from the end carbon atom of an alkane. Name the alkyl groups in the
following table.
Isomers Two compounds with the same molecular formula but different
structures are called isomers. The carbon-to-carbon skeleton in a hydrocarbon
shows the connectivity or constitution of the hydrocarbon. When two
hydrocarbon molecules with the same molecular formula differ in their
connectivity, we call them constitutional isomers. If they have different
formulas, they are not isomers but different compounds. You can draw the
structure of very simple hydrocarbons from their molecular formulas, but two or
more structures are possible for most formulas.
Draw the structures of CH4, C2H2, C2H6 and C2H4 and name them. These
compounds do not have isomers.
Draw the structures of at least three isomers of hexane. Hint: Start with
hexane, then make a pentane with a branch, butane with two branches, etc.
+ r = n + 1 - h/2
Equation 1
[Gross, R.A., Jr. Chem. Educator, [Online] 2003 8(1), 13-14; DOI 10.1333/s00897030646a,
An Equation for Degrees of Unsaturation."]
Use the hydrocarbon equation to calculate DU ( + r) for each compound above
from its molecular formula. Then compare the calculated values to values
obtained by counting the bonds and rings in the structures. We shall use the DU
equation throughout the course.
B = 3n + 1
Equation 2
We must make adjustments to the equation for compounds that have pi bonds and
rings. The total number of bonds B decreases by one for every pi bond or ring in
our compound. Thus, a general equation for the total number of bonds in a
hydrocarbon can be derived by subtracting Equation 1 from Equation 2.
B = 3n + 1 ( + r) = 3n + 1 (n + 1 h/2)
B = 2n + h/2
Equation 3
[Gross, R.A., Jr. Chem. Educator, [Online] 2008 13(5), 284-286; DOI 10.1333/s0089708215a,
"Derivation and Use of a Total-Bonds Equation."]
How many bonds are in an acyclic (no rings) compound of formula C6H6?
Consider how organic molecules are joined together, and derive an equation for
the total number of bonds B in any covalent compound from its molecular
formula.
4. The structure of the hydrocarbon shown below contains carbon-carbon single, double, and
triple bonds. In the spaces provided, show the hybridization, and geometry of the indicated
carbon atoms.
CH3CH2CH=CHCH2CH2C CCH3
5. Circle the structures that represent polar compounds: CH4 CH2BrCl CH3F CHBr3 CCl4
6. Show the number of rings and bonds in the following structures and the sum + r.
r = r = r =
r =
+r= +r= +r=
+r=
7. A compound of formula C 20H36 has no rings. How many sigma bonds does it have? ans. _____
8. Indicate whether the following pair are isomers or are identical compounds. __________________
and
9. Draw skeletal structures of butane and octane (no credit for condensed or alternative structures).