Organic Chemistry

34 CHAPTER 1 Electronic Structure and Bonding • Acids and Bases

Each of the two bonds is formed by the overlap of an orbital of oxygen

with the sorbital of a hydrogen. A lone pair occupies each of the two remaining

orbitals.

The bond angle in water is a little smaller (104.5°) than the tetrahedral bond angle

(109.5°) in methane, presumably because each lone pair “feels”only one nucleus,

which makes the lone pair more diffuse than the bonding pair that “feels”two nuclei

and is therefore relatively confined between them. Consequently, there is more elec-

tron repulsion between lone-pair electrons, causing the bonds to squeeze clos-

er together, thereby decreasing the bond angle.

Compare the potential map for water with that for methane. Water is a polar molecule;

methane is nonpolar.

PROBLEM 16

The bond angles in are greater than __________ and less than __________.

1.12 Bonding in Ammonia and in the Ammonium Ion

The experimentally observed bond angles in are 107.3°. The bond angles indicate

that nitrogen also uses hybrid orbitals when it forms covalent bonds. Like carbon and

oxygen, the one sand three porbitals of the second shell of nitrogen hybridize to form

four degenerate orbitals:

The bonds in are formed from the overlap of an orbital of nitrogen

with the sorbital of a hydrogen. The single lone pair occupies an orbital. The bond

angle (107.3°) is smaller than the tetrahedral bond angle (109.5°) because the electron

sp^3

N¬H NH 3 sp^3

sp^3

ppp

sp^3

s

sp^3 sp^3

hybridization

four orbitals are hybridized

second-shell electrons

of nitrogen

hybrid orbitals

sp^3

NH 3

H 3 O+

O¬H

sp^3

O¬H sp^3

WATER—A UNIQUE COMPOUND

Water is the most abundant compound found in

living organisms. Its unique properties have al-

lowed life to originate and evolve. Its high heat of fusion (the

heat required to convert a solid to a liquid) protects organisms

from freezing at low temperatures because a lot of heat must be

removed from water to freeze it. Its high heat capacity (the heat

required to raise the temperature of a substance a given amount)

minimizes temperature changes in organisms, and its high heat

of vaporization (the heat required to convert a liquid to a gas)

allows animals to cool themselves with a minimal loss of body

fluid. Because liquid water is denser than ice, ice formed on the

surface of water floats and insulates the water below. That is

why oceans and lakes don’t freeze from the bottom up. It is also

why plants and aquatic animals can survive when the ocean or

lake they live in freezes.

104.5°

water

H 2 O

ball-and-stick model of water electrostatic potential map

for water

bond is formed by the overlap

of an sp^3 orbital of oxygen with

lone-pair electrons are in an sp (^3) orbital the s orbital of hydrogen
H
H
O
3-D Molecule:
Water