☰ Contents · Chemistry (Organic chemistry)

Hybridization of the carbon atom

Lessons 17 · 1 lessons · A. Mutalibov, E. Murodov, S. Masharipov, H. Islomova. Organic Chemistry, Grade 10, 1st edition. G‘afur G‘ulom Publishing House, Tashkent, 2017
17

Hybridization of the carbon atom in organic compounds

Textbook: pp. 67–69
GoalDistinguish sp³, sp² and sp hybridization and determine molecular shape and the number of σ- and π-bonds.
New words
hybridization · gibridlanishσ-bond · σ-bog‘π-bond · π-bog‘bond angle · valent burchak
Explanation

In bond formation different atomic orbitals mix to give hybrid orbitals of equal shape and energy; this is hybridization (the theory was proposed by L. Pauling in 1931). In sp³ hybridization one s and three p orbitals mix: four equal orbitals point toward the corners of a tetrahedron, with an angle of 109°28′; such carbon is found in methane and all alkanes and forms four σ-bonds. In sp² hybridization one s and two p orbitals give three orbitals in one plane at 120°; the unhybridized p-orbital stands perpendicular to the plane and forms a π-bond (ethylene, benzene, carbonyl group). In sp hybridization one s and one p orbital mix: two orbitals at 180° (a linear molecule) and two p-orbitals form two π-bonds (acetylene, propyne, a carbon with a triple bond). A quick rule for the hybrid state of carbon: only single bonds — sp³; one double bond — sp²; a triple bond or two double bonds — sp.

Worked examples
Ethylene CH₂=CH₂: both carbons are sp², giving 6 sp² orbitals; σ-bonds: 4 C–H + 1 C–C = 5, plus 1 π-bond. Acetylene HC≡CH: both carbons are sp; 2 σ(C–H) + 1 σ(C–C) = 3 σ and 2 π.
In butadiene-1,3 CH₂=CH–CH=CH₂ all four carbons are sp²; σ-bonds: 6 C–H + 3 C–C = 9; π-bonds: 2. In propyne CH₃–C≡CH the CH₃ carbon is sp³ and the other two are sp.
Class activity

With modelling clay and sticks show the shape of methane (tetrahedron), ethylene (planar) and acetylene (linear). Compare the angles with a protractor. Work with sticks under adult supervision.

Practice
1
What hybridization does carbon in methane have and what is the bond angle?
2
Find the number of sp³ hybrid orbitals in a propane molecule (4 on each C).
3
Find the number of σ-bonds in butadiene-1,3.
4
Why is the acetylene molecule linear?