Chapter 4
Carbon and the Molecular
Diversity of Life
PowerPoint Lectures for
Biology, Seventh Edition
Neil Campbell and Jane Reece
Lectures by Chris Romero
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• Overview: Carbon—The Backbone of Biological
Molecules
• All living organisms
– Are made up of chemicals based mostly on the
element carbon
Figure 4.1
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• Concept 4.1: Organic chemistry is the study of
carbon compounds
• Organic compounds
– Range from simple molecules to colossal ones
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• 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
EXPERIMENT environmental 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 H2O, 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.)
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• Concept 4.2: Carbon atoms can form diverse
molecules by bonding to four other atoms
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The Formation of Bonds with Carbon
• Carbon has four valence electrons
• This allows it to form four covalent bonds with a
variety of atoms
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• 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
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• 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
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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
H C H C
H C H C C
C
Figure 4.5 A-D Cyclohexane Benzene
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Hydrocarbons
• Hydrocarbons
– Are molecules consisting of only carbon and
hydrogen
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• 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
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• 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
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• Enantiomers
– Are important in the pharmaceutical industry
L-Dopa D-Dopa
(effective against (biologically
Figure 4.8 Parkinson’s disease) inactive)
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• Concept 4.3: Functional groups are the parts of
molecules involved in chemical reactions
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The Functional Groups Most Important in the
Chemistry of Life
• Functional groups
– Are the chemically reactive groups of atoms
within an organic molecule
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– Give organic molecules distinctive chemical
properties
OH
CH3
Estradiol
HO
Female lion
OH
CH3
CH3
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
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• Some important functional groups of organic
compounds
FUNCTIONAL
HYDROXYL CARBONYL CARBOXYL
GROUP
O O
OH C C
(may be written HO ) OH
STRUCTURE In a hydroxyl group (—OH), The carbonyl group When an oxygen atom is double-
a hydrogen atom is bonded
to an oxygen atom, which in
>
( CO) consists of a
carbon atom joined to
bonded to a carbon atom that is
also bonded to a hydroxyl group,
turn is bonded to the carbon an oxygen atom by a the entire assembly of atoms is
skeleton of the organic double bond. called a carboxyl group (—
molecule. (Do not confuse COOH).
this functional group with
Figure 4.10 the hydroxide ion, OH–.)
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• Some important functional groups of organic
compounds
NAME OF Alcohols (their specific Ketones if the carbonyl group is Carboxylic acids, or organic
COMPOUNDS names usually end in -ol) 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
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• Some important functional groups of organic
compounds
FUNCTIONAL • Is polar as a result of the • A ketone and an • Has acidic properties because
PROPERTIES electronegative oxygen atom aldehyde may be it is a source of hydrogen ions.
structural isomers with The covalent bond between
drawing electrons toward
different properties, as oxygen and hydrogen is so polar
itself. is the case for acetone that hydrogen ions (H+) tend to
• Attracts water molecules, and propanal. dissociate reversibly; for
helping dissolve organic example,
compounds such as sugars
(see Figure 5.3).
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
Figure 4.10 carboxylate group.
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• 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 atom consists of a sulfur atom phosphorus atom is bonded to four
bonded to two hydrogen bonded to an atom of oxygen atoms; one oxygen is
atoms and to the carbon hydrogen; resembles a bonded to the carbon skeleton; two
skeleton. hydroxyl group in shape. oxygens carry negative charges;
abbreviated P . The phosphate
group (—OPO32–) is an ionized
form of a phosphoric acid group (—
OPO3H2; note the two hydrogens).
Figure 4.10
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• Some important functional groups of organic
compounds
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.
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• Some important functional groups of organic
compounds
• Two sulfhydryl groups • Makes the molecule of which
• Acts as a base; can pick
can interact to help
up a proton from the it is a part an anion (negatively
stabilize protein structure
surrounding solution: charged ion).
(see Figure 5.20).
Can transfer energy between
H organic molecules.
H
N +
N H
H H
(nonionized) (ionized)
• Ionized, with a charge
of 1+, under cellular
Figure 4.10 conditions.
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The Chemical Elements of Life: A Review
• The versatility of carbon
– Makes possible the great diversity of organic
molecules
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