1. Carbon and the Molecular Diversity of Life
Chapter 4
Carbon and the Molecular Diversity of Life

2. Overview: Carbon: The Backbone of Life
Living organisms consist mostly of carbon-based compounds
Carbon is unparalleled in its ability to form large, complex, and diverse molecules
Proteins, DNA, carbohydrates, and other molecules that distinguish living matter are all composed of carbon compounds
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3. Figure 4.1
Figure 4.1 What properties make carbon the basis of all life?

4. Concept 4.1: Organic chemistry is the study of carbon compounds
Organic chemistry is the study of compounds that contain carbon
Organic compounds range from simple molecules to colossal ones
Most organic compounds contain hydrogen atoms in addition to carbon atoms
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5. Vitalism, the idea that organic compounds arise only in organisms, was disproved when chemists synthesized these compounds
Mechanism is the view that all natural phenomena are governed by physical and chemical laws
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6. 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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7. Cooled “rain” containing organic molecules Cold water
Figure 4.2
EXPERIMENT
“Atmosphere”
CH4
Water vapor
Electrode
NH3 H2
Condenser
Cooled “rain” containing organic molecules
Cold water
Figure 4.2 Inquiry: Can organic molecules form under conditions believed to simulate those on the early Earth?
H2O “sea”
Sample for chemical analysis

8. 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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9. The Formation of Bonds with Carbon
With four valence electrons, carbon can form four covalent bonds with a variety of atoms
This ability 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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10. Name and Comment Molecular Formula Structural Formula Ball-and-
Figure 4.3
Name and Comment
Molecular
Formula
Structural
Formula
Ball-and-
Stick Model
Space-Filling
Model
(a) Methane
CH4
(b) Ethane
C2H6
Figure 4.3 The shapes of three simple organic molecules.
(c) Ethene (ethylene)
C2H4

11. 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” that governs the architecture of living molecules
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12. Hydrogen (valence  1) Oxygen (valence  2) Nitrogen (valence  3)
Figure 4.4
Hydrogen
(valence  1)
Oxygen
(valence  2)
Nitrogen
(valence  3)
Carbon
(valence  4)
Figure 4.4 Valences of the major elements of organic molecules.

13. Carbon atoms can partner with atoms other than hydrogen; for example:
Carbon dioxide: CO2
Urea: CO(NH2)2
O = C = O
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14. Figure 4.UN01
Urea
Figure 4.UN01 In-text figure, p. 61

15. Molecular Diversity Arising from Carbon Skeleton Variation
Carbon chains form the skeletons of most organic molecules
Carbon chains vary in length and shape
Animation: Carbon Skeletons
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16. 2-Methylpropane (isobutane)
Figure 4.5
(a) Length
(c) Double bond position
Ethane
Propane
1-Butene
2-Butene
(b) Branching
(d) Presence of rings
Figure 4.5 Four ways that carbon skeletons can vary.
Butane
2-Methylpropane
(isobutane)
Cyclohexane
Benzene

17. (a) Length Ethane Propane Figure 4.5a
Figure 4.5 Four ways that carbon skeletons can vary.

18. (commonly called isobutane)
Figure 4.5b
(b) Branching
Figure 4.5 Four ways that carbon skeletons can vary.
Butane
2-Methylpropane
(commonly called isobutane)

19. (c) Double bond position
Figure 4.5c
(c) Double bond position
1-Butene
2-Butene
Figure 4.5 Four ways that carbon skeletons can vary.

20. (d) Presence of rings Cyclohexane Benzene Figure 4.5d
Figure 4.5 Four ways that carbon skeletons can vary.
Cyclohexane
Benzene

21. 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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22. (a) Part of a human adipose cell (b) A fat molecule
Figure 4.6
Nucleus
Fat droplets
Figure 4.6 The role of hydrocarbons in fats.
10 m
(a) Part of a human adipose cell
(b) A fat molecule

23. Nucleus Fat droplets 10 m Figure 4.6a
Figure 4.6 The role of hydrocarbons in fats.
10 m

24. 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 spatial arrangements
Enantiomers are isomers that are mirror images of each other
Animation: Isomers
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25. (a) Structural isomers
Figure 4.7
(a) Structural isomers
(b) Cis-trans isomers
cis isomer: The two Xs are on the same side.
trans isomer: The two Xs are on opposite sides.
Figure 4.7 Three types of isomers, compounds with the same molecular formula but different structures.
(c) Enantiomers
CO2H
CO2H H
NH2
NH2 H
CH3
CH3
L isomer
D isomer

26. (a) Structural isomers
Figure 4.7a
(a) Structural isomers
Figure 4.7 Three types of isomers, compounds with the same molecular formula but different structures.

27. cis isomer: The two Xs are on the same side.
Figure 4.7b
(b) Cis-trans isomers
cis isomer: The two Xs are on the same side.
trans isomer: The two Xs are on opposite sides.
Figure 4.7 Three types of isomers, compounds with the same molecular formula but different structures.

28. (c) Enantiomers CO2H CO2H H NH2 NH2 H CH3 CH3 L isomer D isomer
Figure 4.7c
(c) Enantiomers
CO2H
CO2H H
NH2
NH2 H
CH3
CH3
Figure 4.7 Three types of isomers, compounds with the same molecular formula but different structures.
L isomer
D isomer

29. 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
Animation: L-Dopa
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30. Effective Enantiomer Ineffective Enantiomer Pain; inflammation
Figure 4.8
Effective
Enantiomer
Ineffective
Enantiomer
Drug
Condition
Pain; inflammation
Ibuprofen
S-Ibuprofen
R-Ibuprofen
Figure 4.8 The pharmacological importance of enantiomers.
Albuterol
Asthma
R-Albuterol
S-Albuterol

31. Concept 4.3: A few chemical groups are key to the functioning of biological molecules
Distinctive properties of organic molecules depend on the carbon skeleton and on the molecular components attached to it
A number of characteristic groups can replace the hydrogens attached to skeletons of organic molecules
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32. The Chemical Groups Most Important in the Processes of Life
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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33. Estradiol Testosterone Figure 4.UN02
Figure 4.UN02 In-text figure, p. 63

34. The seven functional groups that are most important in the chemistry of life:
Hydroxyl group
Carbonyl group
Carboxyl group
Amino group
Sulfhydryl group
Phosphate group
Methyl group
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35. Figure 4.9 Exploring: Some Biologically Important Chemical Groups
Figure 4.9-a
CHEMICAL
GROUP
Hydroxyl
Carbonyl
Carboxyl
STRUCTURE
(may be written HO—)
NAME OF
COMPOUND
Alcohols (Their specific names usually end in -ol.)
Ketones if the carbonyl group is within a carbon skeleton
Carboxylic acids, or organic acids
Aldehydes if the carbonyl group is at the end of the carbon skeleton
EXAMPLE
Ethanol
Acetone
Acetic acid
Figure 4.9 Exploring: Some Biologically Important Chemical Groups
Propanal
FUNCTIONAL
PROPERTIES
• Is polar as a result of the electrons spending more time near the electronegative oxygen
atom.
• A ketone and an aldehyde may be structural isomers with different
properties, as is the case for acetone and propanal.
• Acts as an acid; can donate an
H+ because the covalent bond
between oxygen and hydrogen
is so polar:
• Can form hydrogen bonds with water molecules, helping dissolve
organic compounds such as sugars.
• Ketone and aldehyde groups are also found in sugars, giving rise to two major groups of sugars:
ketoses (containing ketone
groups) and aldoses (containing
aldehyde groups).
Nonionized
Ionized
• Found in cells in the ionized form
with a charge of 1 and called a
carboxylate ion.

36. Figure 4.9 Exploring: Some Biologically Important Chemical Groups
Figure 4.9-b
Amino
Sulfhydryl
Phosphate
Methyl
(may be written HS—)
Amines
Thiols
Organic phosphates
Methylated compounds
Glycine
Cysteine
Glycerol phosphate
5-Methyl cytidine
• Acts as a base; can
pick up an H+ from the
surrounding solution (water, in living
organisms):
• Two sulfhydryl groups can react, forming a covalent
bond. This “cross-linking”
helps stabilize protein
structure.
• Contributes negative charge to
the molecule of which it is a part
(2– when at the end of a molecule,
as above; 1– when located
internally in a chain of
phosphates).
• Addition of a methyl group
to DNA, or to molecules
bound to DNA, affects the
expression of genes.
Figure 4.9 Exploring: Some Biologically Important Chemical Groups
• Arrangement of methyl
groups in male and female
sex hormones affects their
shape and function.
• Cross-linking of cysteines
in hair proteins maintains
the curliness or straightness
of hair. Straight hair can be
“permanently” curled by
shaping it around curlers
and then breaking and
re-forming the cross-linking
bonds.
• Molecules containing phosphate
groups have the potential to react
with water, releasing energy.
Nonionized
Ionized
• Found in cells in the
ionized form with a
charge of 1+.

37. Hydroxyl STRUCTURE NAME OF COMPOUND EXAMPLE FUNCTIONAL PROPERTIES
Figure 4.9a
Hydroxyl
STRUCTURE
Alcohols
(Their specific
names usually
end in -ol.)
NAME OF
COMPOUND
(may be written HO—)
EXAMPLE
• Is polar as a result
of the electrons
spending more
time near the
electronegative
oxygen atom.
FUNCTIONAL PROPERTIES
Figure 4.9 Exploring: Some Biologically Important Chemical Groups
Ethanol
• Can form hydrogen
bonds with water
molecules, helping
dissolve organic
compounds such
as sugars.

38. Carbonyl STRUCTURE NAME OF COMPOUND EXAMPLE FUNCTIONAL PROPERTIES
Figure 4.9b
Carbonyl
STRUCTURE
Ketones if the carbonyl
group is within a
carbon skeleton
NAME OF
COMPOUND
Aldehydes if the carbonyl
group is at the end of the
carbon skeleton
EXAMPLE
A ketone and an
aldehyde may be
structural isomers
with different properties,
as is the case for
acetone and propanal.
FUNCTIONAL PROPERTIES
Ketone and aldehyde
groups are also found
in sugars, giving rise
to two major groups
of sugars: ketoses
(containing ketone
groups) and aldoses
(containing aldehyde
groups).
Figure 4.9 Exploring: Some Biologically Important Chemical Groups
Acetone
Propanal

39. Carboxyl • Acts as an acid; can donate an H+ because the
Figure 4.9c
Carboxyl
STRUCTURE
Carboxylic acids, or organic
acids
NAME OF
COMPOUND
EXAMPLE
• Acts as an acid; can donate an H+ because the
covalent bond between
oxygen and hydrogen is so
polar:
FUNCTIONAL PROPERTIES
Figure 4.9 Exploring: Some Biologically Important Chemical Groups
Acetic acid
Nonionized
Ionized
• Found in cells in the ionized
form with a charge of 1– and
called a carboxylate ion.

40. Amino • Acts as a base; can • Found in cells in the STRUCTURE Amines
Figure 4.9d
Amino
STRUCTURE
Amines
NAME OF
COMPOUND
EXAMPLE
• Acts as a base; can
pick up an H+ from the
surrounding solution
(water, in living
organisms):
FUNCTIONAL PROPERTIES
Figure 4.9 Exploring: Some Biologically Important Chemical Groups
Glycine
Nonionized
Ionized
• Found in cells in the
ionized form with a
charge of 1.

41. Sulfhydryl • Two sulfhydryl groups can • Cross-linking of cysteines
Figure 4.9e
Sulfhydryl
STRUCTURE
Thiols
NAME OF
COMPOUND
(may be
written HS—)
EXAMPLE
• Two sulfhydryl groups can
react, forming a covalent
bond. This “cross-linking”
helps stabilize protein
structure.
FUNCTIONAL PROPERTIES
• Cross-linking of cysteines
in hair proteins maintains
the curliness or straightness
of hair. Straight hair can be
“permanently” curled by
shaping it around curlers
and then breaking and
re-forming the cross-linking
bonds.
Figure 4.9 Exploring: Some Biologically Important Chemical Groups
Cysteine

42. • Contributes negative
Figure 4.9f
Phosphate
STRUCTURE
Organic phosphates
NAME OF
COMPOUND
EXAMPLE
• Contributes negative
charge to the molecule
of which it is a part
(2– when at the end of
a molecule, as at left;
1– when located
internally in a chain of
phosphates).
FUNCTIONAL PROPERTIES
Figure 4.9 Exploring: Some Biologically Important Chemical Groups
Glycerol phosphate
• Molecules containing
phosphate groups have
the potential to react
with water, releasing
energy.

43. • Addition of a methyl group
Figure 4.9g
Methyl
STRUCTURE
Methylated compounds
NAME OF
COMPOUND
EXAMPLE
• Addition of a methyl group
to DNA, or to molecules
bound to DNA, affects the
expression of genes.
FUNCTIONAL PROPERTIES
Figure 4.9 Exploring: Some Biologically Important Chemical Groups
• Arrangement of methyl
groups in male and female
sex hormones affects their
shape and function.
5-Methyl cytidine

44. ATP: An Important Source of Energy for Cellular Processes
One phosphate molecule, adenosine triphosphate (ATP), is the primary energy-transferring molecule in the cell
ATP consists of an organic molecule called adenosine attached to a string of three phosphate groups
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45. Figure 4.UN03 a. b.
Figure 4.UN03 Figure legend question, Figure 4.9

46. Figure 4. UN04
Adenosine
Figure 4.UN04 In-text figure, p. 66

47. The Chemical Elements of Life: A Review
The versatility of carbon makes possible the great diversity of organic molecules
Variation at the molecular level lies at the foundation of all biological diversity
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48. Reacts with H2O Adenosine Adenosine Energy ATP Inorganic phosphate ADP
Figure 4. UN05
Reacts
with H2O
Adenosine
Adenosine
Energy
ATP
Inorganic
phosphate
ADP
Figure 4.UN05 In-text figure, p. 66

49. Figure 4. UN07
Figure 4.UN07 Test Your Understanding, question 2

50. Figure 4. UN08
Figure 4.UN08 Test Your Understanding, question 5

51. Figure 4. UN09
Figure 4.UN09 Test Your Understanding, question 6

52. Figure 4. UN10
Figure 4.UN10 Test Your Understanding, question 11

53. Figure 4. UN11
Figure 4.UN11 Appendix A: answer to Figure 4.4 legend question

54. Figure 4. UN12
Figure 4.UN12 Appendix A: answer to Figure 4.7 legend question

55. Figure 4. UN13
Figure 4.UN13 Appendix A: answer to Concept Check 4.2, question 1

56. Figure 4. UN14
Figure 4.UN14 Appendix A: answer to Concept Check 4.3, question 3

57. Figure 4. UN15
Figure 4.UN15 Appendix A: answer to Test Your Understanding, question 9