Transcript Document

Chapter 4
Carbon and the
Molecular Diversity of
Life
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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
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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
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• The bonding versatility of carbon allows
it to form many diverse molecules,
including carbon skeletons
Name and
Comments
(a) Methane
Molecular Structural
Formula
Formula
Ball-andStick
Model
SpaceFilling
Model
H
CH4
H C
H
H
(b) Ethane
C2H
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(c) Ethene
Figure 4.3 A-C (ethylene)
C2H4
H H
H C C H
H H
H
H
C C
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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• 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 C C C C
H H H H
Butane
(b) Branching
(c) Double bonds
(d) Rings
Figure 4.5 A-D
H H H
H H
H C C H
H H
Ethane
(a) Length
H
H
H
H
H
H H H H
H C C C C
H H
1-Butene
H
H
H
C
C
C H
C
C H
H
C
Cyclohexane
H C C C H
H H H
Propane
H
H C H
H
H
H C C C H
H H H
isobutane
H
H H H H
H C C C C H
H
H
2-Butene
H
H
C C H
C
C
C
Benzene
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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)
Figure 4.6 A, B
(a) A fat molecule
100 µm
(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
H
– Geometric
H C H
H C H
H H H H H
H
H
– Enantiomers
H C C C C C H
H C C C H
(a) Structural isomers
H H H
H H H H H
(b) Geometric isomers
X
H
C C
X
H
H
X
CO2H
(c) Enantiomers
Figure 4.7 A-C
H
C
CH3
C
C
X
H
CO2H
NH2 NH2
C
CH3
H
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• Enantiomers Are important in the
pharmaceutical industry
Figure 4.8
L-Dopa
D-Dopa
(effective against
Parkinson’s disease)
(biologically
inactive)
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Concept check
• 1. Draw a structural formula for C2H4.
• 2. Which molecules in Figure 4.5 are isomers?
Identify the types seen.
• 3. How are gasoline and fat chemically similar?
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Fig. 4.4
Copyright © 2002 Pearson Education, Inc., publishing as Benjamin Cummings
Functional Groups
• Functional groups are
the parts of
molecules involved in
chemical reactions
• They Are the
chemically reactive
groups of atoms
within an organic
molecule
• Give organic
molecules distinctive
chemical properties
Estradiol
HO
Female lion
OH
CH3
CH3
O
Figure 4.9
OH
CH3
Testosterone
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
GROUP
HYDROXYL
CARBONYL
O
OH
(may be written HO
STRUCTURE
Figure 4.10
CARBOXYL
C
C
OH
)
In a hydroxyl group (—
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
ion, OH–.)
O
The carbonyl group
( CO) consists of a
carbon atom joined to
an oxygen atom by a
double bond.

When an oxygen atom is
double-bonded to a carbon
atom that is also bonded to a
hydroxyl group, the entire
assembly of atoms is called a
carboxyl group (—COOH).
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Some important functional groups of
organic compounds
NAME OF
COMPOUNDS
Alcohols (their specific
names usually end in -ol)
Ketones if the carbonyl group
is within a carbon skeleton
Aldehydes if the carbonyl
Carboxylic acids, or organic
acids
group is at the end of the
carbon skeleton
EXAMPLE
H
H
H
C
C
H
H
H
OH
H
Ethanol, the alcohol
present in alcoholic
beverages
H
C
H
C
H
H
Acetone, the simplest ketone
H
Figure 4.10
C
H
H
O
H
H
C
C
H
H
C
H
O
C
OH
Acetic acid, which gives vinegar
its sour tatste
O
C
H
Propanal, an aldehyde
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• Some important functional groups of
organic compounds
AMINO
SULFHYDRYL
H
N
H
The amino group (—NH2)
consists of a nitrogen
atom bonded to two
hydrogen atoms and to
the carbon skeleton.
Figure 4.10
PHOSPHATE
O
SH
(may be written HS
)
O
P OH
OH
The sulfhydryl group
consists of a sulfur atom
bonded to an atom of
hydrogen; resembles a
hydroxyl group in shape.
In a phosphate group, a
phosphorus atom is bonded to
four oxygen atoms; one oxygen is
bonded to the carbon skeleton;
two 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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Concept Check
• 1. What does the term amino acid signify
about the structure of such a molecule?
• 2. What chemical change occurs when ATP
reacts with water and releases energy?
• 3. Suppose you had an organic molecule such
as glycine and you chemically removed the –
NH2 group and replaced it with –COOH. Draw
the structural formula for this molecule and
speculate about its chemical properties.
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