Chapter 4

Carbon and the

Molecular Diversity of
Life

1
 Carbon Chemistry
• Carbon is the Backbone of Biological
Molecules (macromolecules)
• All living organisms Are made up of chemicals
based mostly on the element carbon

Figure 4.1
2
 Carbon Chemistry
• Organic chemistry is the study of carbon
compounds
• Carbon atoms can form diverse molecules by
bonding to four other atoms
• Carbon compounds range from simple
molecules to complex ones
• Carbon has four valence electrons and may
form single, double, triple, or quadruple
bonds

3
 • The bonding versatility of carbon allows
it to form many diverse molecules,
including carbon skeletons
Ball-and-
Name and Molecular Structural Space-
Stick
Comments Formula Formula Filling
Model
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

4
 • 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

5
• Carbon may bond to itself forming carbon
chains
• Carbon chains form the skeletons of most
organic molecules
• Carbon chains vary in length and shape
H H H H H
(a) Length C C H H C C C H
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 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 HH C C
C

Figure 4.5 A-D Cyclohexane Benzene

6
 Hydrocarbons
• Hydrocarbons are molecules consisting of only
carbon and hydrogen
• Hydrocarbons 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
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 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

8
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) 9
 Functional Groups
• Functional groups are
the parts of
molecules involved in OH
chemical reactions Estradiol
CH3

• They Are the

chemically reactive
groups of atoms HO

within an organic Female lion

molecule
OH
• Give organic CH3

molecules distinctive CH3

chemical properties
O
Testosterone

Figure 4.9 Male lion

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• Six functional groups are important in the chemistry of
life
– Hydroxyl
– Carbonyl
– Carboxyl
– Amino
– Sulfhydryl
– Phosphate

11
 Some important functional groups of organic
compounds
FUNCTIONAL
HYDROXYL CARBONYL CARBOXYL
GROUP

O O
OH C C
(may be written HO ) OH

In a hydroxyl group (—
STRUCTURE
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 the hydroxide
Figure 4.10 –
ion, OH .)
The carbonyl group When an oxygen atom is

( CO) consists of a
carbon atom joined to
double-bonded to a carbon
atom that is also bonded to a
an oxygen atom by a hydroxyl group, the entire
double bond. assembly of atoms is called a
carboxyl group (—COOH).

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 Some important functional groups of
organic compounds
NAME OF Alcohols (their specific Ketones if the carbonyl group Carboxylic acids, or organic
COMPOUNDS names usually end in -ol) is within a carbon skeleton acids
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
beverages
Acetone, the simplest ketone its sour tatste

H H
O
H C C C
H H H
Figure 4.10 Propanal, an aldehyde

13
 • 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) The sulfhydryl group In a phosphate group, a

consists of a nitrogen consists of a sulfur atom phosphorus atom is bonded to
atom bonded to two bonded to an atom of four oxygen atoms; one oxygen is
hydrogen atoms and to hydrogen; resembles a bonded to the carbon skeleton;
the carbon skeleton. hydroxyl group in shape. two oxygens 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).

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