The Carbon Atom

2.1 The carbon atom

Atomic number: 6 Electronic configuration: 1s2 2s2 2p2.

1s2 2s2 2p2 Carbon must form 4 bonds covalently, thus it must have 4 unpaired electrons. How? Before that, let us look at a theory: Valence Bond Theory.

2.2 Valence Bond Theory

Valence Bond Theory is related to the Gilbert N. Lewis idea of bonding. It is the formation of covalent bond when two atomic orbitals containing 1 electron each overlap with each other or overlapping of one atomic orbital with 2 electrons with an empty atomic orbital.

H 1s

H 1s
Y

1s

1s

H2

H 1s F 2p

H 1s

2p

HF

However, carbons valence shell configuration is 2s2, 2px1, 2py1, 2pz0, suggests that it can only form 2 bonds. Valence Bond Theory also doesnt explain why in compound such as methane, CH4, the bond angle is 109.50. Solution? HYBRIDIZATION.

2.3 Orbitals hybridization

Orbital hybridization is a modification of Valence Bond Theory. Hybridization is the mixing of orbitals to form new set of hybrid orbitals that gives the most effective overlapping in the correct geometry. In organic chemistry, carbon atom undergoes mainly sp, sp2 or sp3 hybridization.

The Carbon Atom

2.3.1 sp3 hybridization
sp3 hybridization is the mixing of one 2s orbital and three 2p orbitals in the valence shell of the carbon atom to form 4 identical sp3 hybrid orbital. Before hybridization:

After hybridization:

z y

z y

z y

s z y

px z y

py z y

pz z

which can be represented by

The Carbon Atom

As each of the sp3 orbitals contains 1electron, the four sp3 orbitals repel each other to give a tetrahedron in order to minimize electron-electron repulsion. Therefore bond angle of 109.50. All 4 sp3 orbitals are degenerate (same energy level).

Example 1 (methane): Carbon atom in methane undergoes sp3 hybridization. Methane can be formed by overlapping the large lobe of each sp3 orbital with the 1s orbital of H. The hybrid orbitals are orientated at 109.50 to each other in a tetrahedral arrangement. C-H (sp3-s- bond) bonds are bonds.

Example 2 (ethane): Carbon atoms in ethane are sp3 hybridized. Hybrid orbitals are 109.50 to each other forming a tetrahedral shape. C-C are (sp3- sp3- bond) while C-H are (sp3-s- bond).

The Carbon Atom

2.3.2 sp2 hybridization
sp2 hybridization is the mixing of one 2s orbital and two 2p orbitals in the valence shell of the carbon atom to form three identical sp3 hybrid orbital leaving 2pz orbital unchanged.

1s2

(sp2)1 (sp2)1 (sp2)1

pz

Each sp2 hybrid orbitals have one-third s character and two-third p character.

Example 3 (ethene): Carbon atoms in ethene are sp2 hybridized. Three hybridized orbitals are on the plane. Unhybridized pz orbital is perpendicular to the plane. Hybrid orbitals are 1200 to each other forming a trigonal planar. C=C are sp2- sp2- bond and p- p- bond. C-H is sp2-s- bond.

2.3.3 sp hybridization
sp hybridization is the mixing of one 2s orbital and one 2p orbitals in the valence shell of the carbon atom to form two identical sp3 hybrid orbital leaving 2pz and 2py orbital unchanged.

1s2

(sp)1

(sp)1

py

pz

sp hybrid orbitals have half s character and half p character.

The Carbon Atom

Example 4 (ethyne):

Carbon atom is sp hybridized thus leaving two unhydridized p orbitals. The other two sp hybrid orbitals are 1800 to each other in a linear arrangement. The two unhydridized p orbitals are perpendicular to each other. CC bond includes sp- sp- bond, p- p- bond and p- p- bond.

So, how to determine sp, sp2 or sp3 hybridization?

General steps: 1. Circle the atom that you are interested in. (This is to prevent confusion as the compound given could be a complex one.) 2. Count the number of bonds around the circled atom. Treat double and triple bonds as a SINGLE bond. 3. Count the number of lone PAIRS of electrons if there is. 4. Add the numbers together. Number 2 3 4 Hybridization sp sp2 sp3 Shape/bond angle Linear/1800 Trigonal planar/1200 Tetrahedron/109.50

C1: There are 4 bonds (dont forget the hidden hydrogens) and 0 lone pairs of electrons around C1, thus C1 is sp3 hybridized. C2: There are 3 bonds (treat double bond as single bond) and 0 lone pairs of electrons around C2, thus C2 is sp2 hybridized. C3: There are 3 bonds (treat double bond as single bond) and 0 lone pairs of electrons around C3, thus C3 is sp2 hybridized. O4: There are 2 bonds and 2 lone pairs of electrons, total of 4. Thus O4 is sp3 hybridized. 5