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: CarbonThe 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
EXPERIMENT conditions on the lifeless, primordial Earth. As shown in this recreation,
In 1953, Stanley Miller simulated what were thought to be environmental 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.

RESULTS

A variety of organic compounds that play key roles in living cells were synthesized in Millers apparatus. Organic compounds may have been synthesized abiotically on the this hypothesis in more detail in Chapter 26.)

CONCLUSION early Earth, setting the stage for the origin of life. (We will explore Figure 4.2
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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 Comments Molecular Structural Formula Formula
H

Ball-andStick Model

SpaceFilling Model

(a) Methane

CH4

H C H H H

(b) Ethane

C2H
6

H C C H H H H H H

(c) Ethene Figure 4.3 A-C (ethylene)

C2H4

C C

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 The electron configuration of carbon

Gives it covalent compatibility with many different elements
Hydrogen (valence = 1) Oxygen (valence = 2) Nitrogen Carbon (valence = 4)

(valence = 3)

H
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
(a) Length H H H H C C C H H H H 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 2-methylpropane Butane (commonly called isobutane) H H H H H H H H (c) Double bonds H H C C C C H C C C C H H H H H 1-Butene 2-Butene H H H H C H H C C H C H (d) Rings H C C H C C H H H C C C H H H C C H H H Ethane Cyclohexane Benzene

Figure 4.5 A-D

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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 cells organic molecules
Fat droplets (stained red)

Figure 4.6 A, B

(a) A fat molecule

100 m (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
(a) Structural isomers

H H H H H H C C C C C H H H H H H X H

H H C H H C H H H H C C C H H H H H X CO2H

(b) Geometric isomers

C C

C C

X H

H CO2H C CH3 NH2NH2

(c) Enantiomers

C CH3

Figure 4.7 A-C

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 Enantiomers
Are important in the pharmaceutical industry

L-Dopa
Figure 4.8

D-Dopa (biologically inactive)

(effective against Parkinsons disease)

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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
Figure 4.9

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 CARBOXYL

O C OH

OH
(may be written HO )

STRUCTURE 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.) Figure 4.10

The carbonyl group ( CO) consists of a carbon atom joined to an oxygen atom by a double bond.

When an oxygen atom is doublebonded 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 Carboxylic acids, or organic within a carbon skeleton acids Aldehydes if the carbonyl group is at the end of the carbon skeleton

EXAMPLE

H H C H

H C H OH H

H C H H C

O H H C

H C H C

OH

Ethanol, the alcohol present in alcoholic beverages

H
Acetone, the simplest ketone

Acetic acid, which gives vinegar

its sour tatste

H H C H Figure 4.10

H C H C

Propanal, an aldehyde

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 Some important functional groups of organic compounds

FUNCTIONAL Is polar as a result of the PROPERTIES electronegative oxygen atom
drawing electrons toward itself. Attracts water molecules, helping dissolve organic compounds such as sugars A ketone and an aldehyde may be structural isomers with different properties, as is the case for acetone and propanal. Has acidic properties because it is a source of hydrogen ions. The covalent bond between oxygen and hydrogen is so polar that hydrogen ions (H+) tend to dissociate reversibly; for example,

(see Figure 5.3).

H H C H C OH O H H C H C O O

+ H+

Figure 4.10

In cells, found in the ionic form, which is called a carboxylate group.

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 Some important functional groups of organic compounds

AMINO
H N

SULFHYDRYL
SH (may be written HS )

PHOSPHATE
O O P OH OH

The amino group (NH2) consists of a nitrogen atom bonded to two hydrogen atoms and to the carbon skeleton.

The sulfhydryl group consists of a sulfur atom bonded to an atom of hydrogen; resembles a hydroxyl group in shape.

Figure 4.10

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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 Some important functional groups of organic compounds

O C HO

H C H

H H C H

H C H SH H

OH OH H C H C H C H O

O P O O

N
H

Glycine

Ethanethiol Glycerol phosphate

Figure 4.10

Because it also has a carboxyl group, glycine is both an amine and a carboxylic acid; compounds with both groups are called amino acids.

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 Some important functional groups of organic compounds

Acts as a base; can pick Two sulfhydryl groups can Makes the molecule of which

up a proton from the surrounding solution:

interact to help stabilize protein structure (see Figure 5.20).

H N H
(nonionized)

H
+N

it is a part an anion (negatively charged ion). Can transfer energy between organic molecules.

H
(ionized)

Ionized, with a charge

Figure 4.10

of 1+, under cellular 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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