II.

Propert ies of Water

1. Ice and Liquid water structure
2. Cohesion / Surface Tension
3. High Heat Capacity
4. Solvent Properties
5. Dissociation: Acids & Bases / pH
II. Organic Chemistry
A. Hydrocar bons--nonpolar
1. alkanes-only single bonds
2. alkenes- C=C double bonds
3. aromatic-cyclic based on benzene
B. Funct ional Groups: alcohol, aldehyde, ketone, carboxyl, amine,
organophosphate, sulfhydral
1. polar bonds between C and more electronegative atoms (O and N)
2. Combine two functional groups ester = alcohol + acid
3. amide = amine + acid
C. Isomers
1. Same chemical formula but differ in arrangement of atoms in space
2. Enantiomers (Optical Isomers): C can be bonded to 4 different groups
in 2 ways producing molecules that are mirror images of one another
that cannot be superimposed
 Water As A Solvent For Life

75% of the Earth’s

surface is covered
with water

Water is essential for life on Earth

All living organisms require water more than

any other substance
 Fig. 3.2: Water: Structure and Properties

Hydrogen bond
acceptors

104.5°

Hydrogen bond
donors
Water’s molecular structure and capacity to donate
and accept hydrogen bonds give it unusual critical
properties that are significant for life
 Fig. 3.6: Five Critical Properties of Water
1. Ice and liquid water structure

Hydrogen
bond
Ice Liquid water
Hydrogen bonds are stable Hydrogen bonds break and re-form

Temperature ≤ 0°C Temperature > 0°C < 100°C

• Ice is less dense than liquid water
• Water is liquid at a relatively high temperature > 0°C
(Methane (CH4) is similar in size but liquid only below -161°C)
Fig. 3.3/3.4: Five Critical Properties of Water – 2. Cohesion

Hydrogen bonds
hold water molecules
together in liquid

High Surface tension

Water transport
Fig. 3.4
in plants
 Five Critical Properties of Water
3. Moderation of temperature

Heat energy can be absorbed by

breaking hydrogen bonds

Water has a high specific heat capacity

specific heat capacity = amount of energy required to raise
temperature of 1 g of water by 1°C (1 calorie, 1 cal)
 Large bodies of water stabilize the air temperature.
 Fig. 2.15/3.7: Five Critical Properties of Water
4.Water as a solvent

A sphere of water
molecules,
called a hydration
shell, surrounds
each solute ion

Fig. 2.15 Fig. 3.7

 Fig. 3.8: Five Critical Properties of Water
4. Water as a solvent (Cont’d)

Fig. 3.8
(a) Lysozyme molecule in a
nonaqueous environment
(b) Lysozyme molecule (purple) in an aqueous
environment
(c) Ionic and polar regions
on the protein’s surface
attract water molecules.

Review solute concentration in aqueous solutions (Molarity)

(page 51 – 52 of text)
Five Critical Properties of Water
4. Water as a solvent (Cont’d)
Page 53 OH-
(hydroxide ion)
H3O+
(hydronium ion)

This reaction is frequently abbreviated as:

OH -
H 2O H+ +
The KW is the ion product of water,

Kw = [H+][OH-] = 1.0 x 10-14 M2 at 25°C

Thus, in pure water, [H+] = [OH-] = 1.0 x 10-7 M
 pH SCALE - 1.0 x 10-7 M is a very small number and
Fig. 3.9:
can change by orders of magnitude (powers of 10x)  pH

pH = -log[H+] = 7
in pure water at 25°C = neutral pH

“Physiological pH”
(pH 6.5 – 8.0)
 O O
CH3-C CH3-C + H+
OH O-

NH3 + H+ NH4+
 Ka pKa
CH3COOH CH3COO- + H+ 1.8 x 10-5 M 4.7

NH4+ NH3 + H+ 5.8 x 10-10 M 9.2

HA A- + H+
[H+][A-]
Acid ionization constant, Ka = pKa = -log Ka
[HA]

pKa is a measure of propensity to dissociate:

if pH < pKa the HA form predominates
if pH > pKa the A- form predominates
 [HA] >> [A-]
Buffers keep pH relatively
constant in the range
around pKa value by
[HA] = [A-] accepting or donating H+
from solution
[A-] >> [HA]

O Response to decrease [H+] O

CH3-C CH3-C
OH Response to increase [H+] O-
 Organic Chemistry

The chemistry of molecules containing

carbon bonded to other elements,
principally: H, O, N, P, S …
Hydrocarbons are Nonpolar (electrons are equally
distributed) and do not mix freely with water
 they are Hydrophobic.

109°

120°
Fig. 4-3
Fig. 4.3: The Shapes of Three Simple Organic Molecules
Name and Molecular Structural Ball-and- Space-Filling
Comment Formula Formula Stick Model Model
(a) Methane

CH4

(b) Ethane

C 2H 6

(c) Ethene
(ethylene)
C 2H 4
 Hydrocarbons -- organic compounds containing only
carbon and hydrogen. These are the most reduced organic
compounds and react vigorously (i.e. burn) with oxygen.

CH4 + 2O2 CO2 + 2H2O + Heat

+ + + Heat

2 2
Methane Carbon
Oxygen Water
(natural gas) Dioxide
 Fig. 4.5: Various Hydrocarbons
(a) Length (c) Double bond position

Ethane Propane 1-Butene 2-Butene

(b) Branching (d) Presence of rings

Butane 2-Methylpropane Cyclohexane Benzene

(isobutane)
HHHHHHHH
H-C-C-C-C-C-C-C-C-H
HHHH HHHH
Octane C8H18: A major component of gasoline.
Aromatic Hydrocarbons -- are a special class of hydrocarbons in which
atoms are arranged in a ring structure and are connected by σ-bonds and a
system of π-bonds around the ring. The simplest example is benzene,
C6H6, and as shown below all atoms lie on a plane with bond angles of 120°

120°
 Fig. 4.4: Carbon also forms bonds with a variety of other
Elements
Hydrogen Oxygen Nitrogen Carbon
(valence = 1) (valence = 2) (valence = 3) (valence = 4)

H O N C

Carbon dioxide
(CO2) Urea
CO(NH2)
O C O
Urea
 Functional Groups
Here “R” represents the rest of the molecule
Carbonyls
O
O O O
R–OH R–C R–C R–C R–NH2 R–SH R–O–P–OH
H R’ OH OH
Alcohol Aldehyde Ketone Carboxylic Acid Amine Sulfhydral Organic Phosphate

Ethanol Acetone Acetic Acid

Fig. 5-2a
Fig. 5.2a: The Synthesis of Polymers

(a) Dehydration reaction: synthesizing a polymer

1 2 3

Short polymer Unlinked monomer

Dehydration removes
a water molecule,
forming a new bond.

1 2 3 4

Longer polymer
 Linking Functional Groups Polymers

Organic molecules with certain functional groups can be joined by a

covalent bond formed when a molecule of water is removed; this allows
the creation of new types of organic molecules.
Ester Amide

O O O O
R–C R–C + H2O R–C R–C + H2O
OH + HO–R’ O-R’ OH + H N-R’
N-R’ H
H

O O
R-OH + HO-P-OH R-O-P-OH + H2O
O- O-
Fig. 4.6: Ester bonds link fatty acid carboxyl groups to
OH- groups of Glycerol

Nucleus

Fat droplets

10 µm
(a) Part of a human adipose cell (b) A fat molecule
a.k.a. Triglyceride
Isomers: Molecules that have the same chemical formula,
i.e. the same number of each of the different kinds of atoms.
Fig. 4.7: There are different classes of Isomers

cis isomer: The two X’s trans isomer: The two X’s
are on the same side. are on opposite sides.

L isomer D isomer
Fig. 4-8 Fig. 4.8: Pharmacological Importance of Enantiomers

Effective Ineffective
Drug Condition
Enantiomer Enantiomer

Ibuprofen Pain;
inflammation
S-Ibuprofen R-Ibuprofen

Albuterol Asthma

R-Albuterol S-Albuterol
Thalidomide was first used as a sedative and anti-nausea medication, but
was found to cause serious birth defects when pregnant women take it
during their first trimester.