Chapter 4

Carbon and the Molecular

Diversity of Life
MATERIALS FOR
BIOLOGY OLYMPIAD PREPARATION
PowerPoint Lectures for DWIWARNA HIGH BOARDING SCHOOL, BOGOR
Biology, Seventh Edition INSTRUCTOR:
Neil Campbell and Jane Reece WIDIATI and SUGANDA KUSMANA
CORRESPONDENCE:
suganda_kusmana@yahoo.com
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 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 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 C2H
H C C H
6
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 NH2NH2 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 ( CO) consists of a bonded to a carbon atom that is
to an oxygen atom, which in carbon atom joined to 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 the
Figure 4.10 hydroxide ion, OH–.)

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 • Some important functional groups of organic
compounds
Ketones if the carbonyl group is Carboxylic acids, or organic
NAME OF Alcohols (their specific
within a carbon skeleton
COMPOUNDS names usually end in -ol) 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.
drawing electrons toward structural isomers with The covalent bond between
different properties, as oxygen and hydrogen is so polar
itself. that hydrogen ions (H+) tend to
is the case for acetone
 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

consists of a nitrogen atom
bonded to two hydrogen
atoms and to the carbon
skeleton.
Figure 4.10
In a phosphate group, a
consists of a sulfur atom
phosphorus atom is bonded to four
bonded to an atom of
oxygen atoms; one oxygen is
hydrogen; resembles a
bonded to the carbon skeleton; two
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).

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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 H H O

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 can  Makes the molecule of which

 Acts as a base; can pick
interact to help stabilize it is a part an anion (negatively
up a proton from the
protein structure (see charged ion).
surrounding solution:
Figure 5.20). Can transfer energy between
organic molecules.
H 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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