Carbon and the Molecular

Diversity of Life
Carbon—The Backbone of Biological Molecules

All living organisms

Are made up of chemicals based mostly on
the element carbon

Figure 4.1
 Organic chemistry is the study of carbon
compounds
 Organic compounds
– Range from simple molecules to colossal
ones
The concept of vitalism
Is the idea that organic compounds arise only within living organisms
Was disproved when chemists synthesized the compounds in the
laboratory

In 1953, Stanley Miller simulated what were thought to be environmental

EXPERIMENT conditions on the lifeless, primordial Earth. As shown in this recreation,
Miller used electrical discharges (simulated lightning) to trigger reactions
in a primitive “atmosphere” of H 2O, H2, NH3 (ammonia), and CH4 (methane)
—some of the gases released by volcanoes.

A variety of organic compounds that play key roles in living cells were
RESULTS synthesized in Miller’s apparatus.
Organic compounds may have been synthesized abiotically on the
CONCLUSION early Earth, setting the stage for the origin of life. (We will explore
Figure 4.2 this hypothesis in more detail in Chapter 26.)
 Carbon atoms can form diverse molecules by
bonding to four other atoms

• Carbon has four valence electrons

• This allows it to form four covalent bonds with a
variety of atoms
The bonding versatility of carbon
Allows it to form many diverse molecules, including carbon skeletons

Name and Molecular Structural Ball-and- Space-

Comments Formula Formula Stick Model Filling
Model
H
(a) Methane CH4 H C H
H

H H
(b) Ethane
C2H6 H C C H
H H

(c) Ethene H H
C2H4 C C
Figure 4.3 A-C (ethylene) H H
The electron configuration of carbon
Gives it covalent compatibility with many different elements

Hydrogen Oxygen Nitrogen Carbon

(valence = 1) (valence = 2) (valence = 3) (valence = 4)

H O N C

Figure 4.4
Molecular Diversity Arising from Carbon Skeleton
Variation
Carbon chains form the skeletons of most organic
molecules vary in length and shape

H H H H H
(a) Length H C C C H
H C C H
H H H H H
Ethane Propane
H
H C H
H H H H H H
(b) Branching H C C C C H H C C C H
H H H H H H H
Butane 2-methylpropane
(commonly called isobutane)
H H H H H H H H
(c) Double bonds H C C C C H H C C C C H
H H H H
1-Butene 2-Butene
H H H
H C H H
(d) Rings H C C H C C H
C
H
H C C H H C C
C

Figure 4.5 A-D Cyclohexane Benzene

 Hydrocarbons
• Are molecules consisting of only carbon and
hydrogen
• Are found in many of a cell’s organic
molecules Fat droplets (stained red)

100 µm
Figure 4.6 A, B (a) A fat molecule (b) Mammalian adipose cells
Isomers
Isomers
Are molecules with the same molecular formula but
different structures and properties
 Three types of isomers are

Structural
Geometric
Enantiomers
H
H C H
H C H
H H H H H H H
(a) Structural isomers H C C C C C H H C C C H
H H H H H H H H
X X H X
(b) Geometric isomers C C C C
H H X H
CO2H CO2H

(c) Enantiomers C C
H NH2 NH2 H
CH3 CH3

Figure 4.7 A-C

Enantiomers
Are important in the pharmaceutical industry

L-Dopa D-Dopa
(effective against (biologically
Figure 4.8 Parkinson’s disease) inactive)
The Functional Groups Most Important in
the Chemistry of Life

Are the chemically reactive groups of atoms within an organic molecule

CH3OH
Estradiol

HO

Female lion

CH3OH
CH3

O Testosterone
Figure 4.9 Male lion
Six functional groups are important
in the chemistry of life
Hydroxyl
Carbonyl
Carboxyl
Amino
Sulfhydryl
Phosphate
 • Some important functional groups of organic
compounds
FUNCTIONAL
HYDROXYL
GROUP
OH
(may be written HO
STRUCTURE In a hydroxyl group (—OH), a
hydrogen atom is bonded to
an oxygen atom, which in
turn is bonded to the carbon
skeleton of the organic
molecule. (Do not confuse
this functional group with
Figure 4.10 the hydroxide ion, OH–.)
CARBONYL CARBOXYL
O O
C C
) OH
The carbonyl group When an oxygen atom is double-

( CO) consists of a
carbon atom joined to
bonded to a carbon atom that is
also bonded to a hydroxyl group,
an oxygen atom by a the entire assembly of atoms is
double bond. called a carboxyl group (—
COOH).
 • Some important functional groups of organic
compounds
NAME OF Alcohols (their specific Ketones if the carbonyl group is
within a carbon skeleton Carboxylic acids, or organic acids
COMPOUNDS names usually end in -ol)
Aldehydes if the carbonyl group
is at the end of the carbon
skeleton
EXAMPLE H H H O H O
H C C OH H C C H C C
H OH
H H H C H
Ethanol, the alcohol
H
present in alcoholic H Acetic acid, which gives vinegar its
beverages
Acetone, the simplest ketone sour tatste

H H
O
H C C C
H H H
Figure 4.10 Propanal, an aldehyde
 • Some important functional groups of organic
compounds
FUNCTIONAL  Is polar as a result of the
PROPERTIES electronegative oxygen atom
drawing electrons toward
itself.
 Attracts water molecules,
helping dissolve organic
compounds such as sugars
(see Figure 5.3).
Figure 4.10
 A ketone and an
 Has acidic properties because it
aldehyde may be
is a source of hydrogen ions.
structural isomers with
The covalent bond between
different properties, as
oxygen and hydrogen is so polar
is the case for acetone
that hydrogen ions (H+) tend to
and propanal.
dissociate reversibly; for example,
H O H O
H C C H C C + H+
H OH H O
 In cells, found in the ionic
form, which is called a
carboxylate group.
 • Some important functional groups of organic
compounds

AMINO SULFHYDRYL PHOSPHATE

H SH O
N (may be written HS ) O P OH
H OH

The amino group (—NH2) In a phosphate group, a

The sulfhydryl group consists
consists of a nitrogen atom phosphorus atom is bonded to four
of a sulfur atom bonded to an
bonded to two hydrogen oxygen atoms; one oxygen is bonded
atom of hydrogen; resembles a
atoms and to the carbon to the carbon skeleton; two oxygens
hydroxyl group in shape.
skeleton. carry negative charges; abbreviated
P . The phosphate group (—OPO32–)
is an ionized form of a phosphoric
acid group (—OPO3H2; note the two
Figure 4.10 hydrogens).
 H H H H OH OH H O
O
C C N H C C SH H C C C O P O

HO H H H H H O
H H

Glycine Ethanethiol
Glycerol phosphate

Because it also has a carboxyl

group, glycine is both an amine
and a carboxylic acid;
compounds with both groups
Figure 4.10 are called amino acids.