Chapter 4

Carbon: The
Basis of
Molecular
Diversity

Lecture Presentations by
Nicole Tunbridge and
© 2018 Pearson Education Ltd.
Kathleen Fitzpatrick
Carbon: The Backbone of Life

 Living organisms consist mostly of carbon-based

compounds
 Carbon is unparalleled in its ability to form large,
complex, and varied molecules
 Proteins, DNA, carbohydrates, and other molecules
that distinguish living matter are all composed of
carbon compounds

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Figure 4.1

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Concept 4.1: Organic chemistry is the study of
carbon compounds
 Organic chemistry is the study of compounds that
contain carbon, regardless of origin
 Organic compounds range from simple molecules to
colossal ones

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Organic Molecules and the Origin of Life on
Earth
 Stanley Miller’s classic experiment demonstrated the
abiotic synthesis of organic compounds
 Experiments support the idea that abiotic synthesis
of organic compounds, perhaps near volcanoes,
could have been a stage in the origin of life

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Figure 4.2
“Atmosphere”
CH4
Water vapor
Electrode

Condenser

Cooled “rain”
containing Cold
organic water
molecules

H2O
“sea”

Sample for
chemical analysis
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 The overall percentages of the major elements of
life—C, H, O, N, S, and P—are quite uniform from
one organism to another
 Because of carbon’s ability to form four bonds, these
building blocks can be used to make an
inexhaustible variety of organic molecules
 The great diversity of organisms on the planet is due
to the versatility of carbon

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Concept 4.2: Carbon atoms can form diverse
molecules by bonding to four other atoms
 Electron configuration is the key to an atom’s
characteristics
 Electron configuration determines the kinds and
number of bonds an atom will form with other atoms

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The Formation of Bonds with Carbon

 With four valence electrons, carbon can form four

covalent bonds with a variety of atoms
 This makes large, complex molecules possible
 In molecules with multiple carbons, each carbon
bonded to four other atoms has a tetrahedral shape
 However, when two carbon atoms are joined by a
double bond, the atoms joined to the carbons are
in the same plane as the carbons

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Figure 4.3

Molecule Molecular Structural Ball-and-Stick Model Space-Filling

Formula Formula Model

(a) Methane

CH4

(b) Ethane

C2H6

(c) Ethene (ethylene)

C2H4

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 The number of unpaired electrons in the valence
shell of an atom is generally equal to its valence, the
number of covalent bonds it can form

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Figure 4.4

Hydrogen Oxygen Nitrogen Carbon

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

H O N C

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 The electron configuration of carbon gives it covalent
compatibility with many different elements
 The valences of carbon and its most frequent
partners (hydrogen, oxygen, and nitrogen) are the
building code for the architecture of living molecules

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 Carbon atoms can partner with atoms other than
hydrogen, such as the following:
 Carbon dioxide: CO2

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  Urea: CO(NH2)2

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Molecular Diversity Arising from Variation in
Carbon Skeletons
 Carbon chains form the skeletons of most organic
molecules
 Carbon chains vary in length and shape

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Figure 4.5

(a) Length (c) Double bond position

Ethane Propane 1-Butene 2-Butene

(b) Branching (d) Presence of rings

Butane 2-Methylpropane Cyclohexane Benzene

(isobutane)

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Animation: Carbon Skeletons

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Hydrocarbons

 Hydrocarbons are organic molecules consisting of

only carbon and hydrogen
 Many organic molecules, such as fats, have
hydrocarbon components
 Hydrocarbons can undergo reactions that release a
large amount of energy

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Figure 4.6

Nucleus
Fat droplets

10 µm

(a) Part of a human adipose cell (b) A fat molecule

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Isomers

 Isomers are compounds with the same molecular

formula but different structures and properties
 Structural isomers have different covalent
arrangements of their atoms
 Cis-trans isomers have the same covalent bonds but
differ in their spatial arrangements
 Enantiomers are isomers that are mirror images
of each other

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Figure 4.7

(a) Structural isomers (c) Enantiomers

Pentane 2-Methylbutane L isomer D isomer

(b) Cis-trans isomers

cis isomer: trans isomer:

The two Xs are on The two Xs are
the same side. on opposite sides.

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Figure 4.7a

(a) Structural isomers

Pentane 2-Methylbutane

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Figure 4.7b

(b) Cis-trans isomers

cis isomer: The two Xs trans isomer: The two Xs

are on the same side. are on opposite sides.

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Figure 4.7c

(c) Enantiomers
CO2H CO2H

C C
H NH2 NH2 H
CH3 CH3

L isomer D isomer

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Animation: Isomers

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 Enantiomers are important in the pharmaceutical
industry
 Two enantiomers of a drug may have different
effects
 Usually, only one isomer is biologically active
 Differing effects of enantiomers demonstrate that
organisms are sensitive to even subtle variations
in molecules

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Figure 4.8

Effective Ineffective
Drug Effects Enantiomer Enantiomer

Reduces
Ibuprofen inflammation
and pain
S-Ibuprofen R-Ibuprofen

Relaxes bronchial
(airway) muscles,
Albuterol improving airflow
in asthma
patients R-Albuterol S-Albuterol

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Animation: L-Dopa

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Concept 4.3: A few chemical groups are key to
molecular function
 Distinctive properties of organic molecules depend
on the carbon skeleton and on the chemical groups
attached to it
 A number of characteristic groups can replace
the hydrogens attached to skeletons of organic
molecules

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The Chemical Groups Most Important in the
Processes of Life
 Estradiol and testosterone are both steroids with
a common carbon skeleton, in the form of four fused
rings
 These sex hormones differ only in the chemical
groups attached to the rings of the carbon skeleton

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Figure 4.UN04

Estradiol Testosterone

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 Functional groups are the components of organic
molecules that are most commonly involved in
chemical reactions
 The number and arrangement of functional groups
give each molecule its unique properties

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 The seven functional groups that are most important
in the chemistry of life are the following:
 Hydroxyl group
 Carbonyl group
 Carboxyl group
 Amino group
 Sulfhydryl group
 Phosphate group
 Methyl group

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Figure 4.9
Chemical Group Group Properties Examples

Hydroxyl group (—OH) Alcohol

Ethanol

Carbonyl group ( C ═ O) Ketone

Aldehyde

Acetone Propanal

Carboxyl group (—COOH) Carboxylic acid

or organic acid

Acetic acid

Amino group (—NH2) Amine

Glycine

Sulfhydryl group (—SH) Thiol

Cysteine

Phosphate group (—OPO32−) Organic

phosphate
Glycerol
phosphate

Methyl group (—CH3) Methylated

compound
5-Methylcytosine

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Figure 4.9a

Chemical Group Compound Name Examples

Hydroxyl group (—OH) Alcohol
Ethanol

Carbonyl group ( C ═ O) Ketone

Aldehyde

Acetone Propanal

Carboxyl group (—COOH) Carboxylic acid

or organic acid

Acetic acid

Amino group (—NH2) Amine

Glycine

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Figure 4.9aa

Hydroxyl group (—OH)

Ethanol, the alcohol
present in
alcoholic beverages
(may be written HO—)

Polar due to electronegative oxygen. Forms hydrogen bonds with water.

Compound name: Alcohol

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Figure 4.9ab

Carbonyl group ( C ═ O)

Acetone, Propanal,
the simplest ketone an aldehyde

Sugars with ketone groups are called ketoses; those with aldehydes
are called aldoses.
Compound name: Ketone or aldehyde

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Figure 4.9ac

Carboxyl group (—COOH)

Acetic acid, which Ionized form of —COOH

gives vinegar its (carboxylate ion),
sour taste found in cells
Acts as an acid.
Compound name: Carboxylic acid, or organic acid

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Figure 4.9ad

Amino group (—NH2)

Glycine, an amino acid Ionized form

(note its carboxyl group) of —NH2,
found in cells
Acts as a base.
Compound name: Amine

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Figure 4.9b

Chemical Group Compound Name Examples

Sulfhydryl group (—SH) Thiol

Cysteine

Phosphate group Organic

(—OPO32−) phosphate

Glycerol
phosphate

Methyl group (—CH3) Methylated

compound 5-Methylcytosine

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Figure 4.9ba

Sulfhydryl group (—SH)

Cysteine, a sulfur-
containing amino acid

(may be written HS—)

Two —SH groups can react, forming a “cross-link” that helps stabilize
protein structure.
Compound name: Thiol

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Figure 4.9bb

Phosphate group (—OPO32−)

Glycerol phosphate,
which takes part in
many important
chemical reactions
in cells

Contributes negative charge. When attached, confers on a molecule the

ability to react with water, releasing energy.
Compound name: Organic phosphate

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Figure 4.9bc

Methyl group (—CH3)

5-Methylcytosine, a
component of DNA
that has been modified
by addition of a methyl
group

Affects the expression of genes. Affects the shape and function of

sex hormones.
Compound name: Methylated compound

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ATP: An Important Source of Energy for
Cellular Processes
 An important organic phosphate is adenosine
triphosphate (ATP)
 ATP consists of an organic molecule called
adenosine attached to a string of three phosphate
groups
 ATP stores the potential to react with water
 This reaction releases energy that can be used by
the cell

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Figure 4.UN05

Adenosine

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Figure 4.UN06

Reacts
with H2O
P P P Adenosine P P Adenosine Pi Energy

ATP ADP Inorganic

phosphate

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