Question 23.5: Visualizing Orbital Overlap in Organic Molecules with Single...
Visualizing Orbital Overlap in Organic Molecules with Single Bonds
Draw an orbital overlap picture for methanol (commonly known as wood alcohol), CH_{3}OH.
STRATEGY
Draw the electron-dot structure for CH_{3}OH and determine the hybridization on each central atom. Overlap atomic or hybrid orbitals to make single bonds and fill in nonbonding orbitals with lone pairs as indicated by the electron-dot structure.
The electron-dot structure for methanol is:
The carbon atom forms four bonds; three with hydrogen and one with oxygen and is therefore sp³ hybridized. Oxygen has two bonds and two lone pairs and is also sp³ hybridized. Overlap three carbon sp³ orbitals with 1s orbitals of hydrogen to form C-H bonds. Overlap the remaining carbon sp³ orbital with an oxygen sp³ orbital to form the C-O bond. Account for the O-H bond by overlapping another oxygen sp³ orbital with the 1s orbital of hydrogen. The two lone pairs on oxygen are placed in the two nonbonding sp³ orbitals of oxygen.
