04- carbon chemistry text

Copyright © 2005 Pearson Education, Inc. publishing as Benjamin Cummings

PowerPoint Lectures for Biology, Seventh Edition

Neil Campbell and Jane Reece

Lectures by Chris Romero

Chapter 4

Carbon and the Molecular Diversity of Life


• Overview: Carbon—The Backbone of Biological Molecules

• All living organisms

– Are made up of chemicals based mostly on the element carbon

Figure 4.1


• Concept 4.1: Organic chemistry is the study of carbon compounds

• Organic compounds

– Range from simple molecules to colossal ones


• 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 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 synthesized in Miller’s apparatus.

EXPERIMENT

RESULTS

CONCLUSIONOrganic compounds may have been synthesized abiotically on the early Earth, setting the stage for the origin of life. (We will explore this hypothesis in more detail in Chapter 26.)Figure 4.2


• Concept 4.2: Carbon atoms can form diverse molecules by bonding to four other atoms


The Formation of Bonds with Carbon

• Carbon has four valence electrons

• This allows it to form four covalent bonds with a variety of atoms


• The bonding versatility of carbon

– Allows it to form many diverse molecules, including carbon skeletons

(a) Methane

(b) Ethane

(c) Ethene (ethylene)

Molecular Formula

Structural Formula

Ball-and-Stick Model

Space-Filling Model

H

H

H

H

H

HH

H

HH

H H

HH

C

C C

C C

CH4

C2H6

C2H4

Name and Comments

Figure 4.3 A-C


• The electron configuration of carbon

– Gives it covalent compatibility with many different elements

H O N C

Hydrogen

(valence = 1)

Oxygen

(valence = 2)

Nitrogen

(valence = 3)

Carbon

(valence = 4)

Figure 4.4


Molecular Diversity Arising from Carbon Skeleton Variation

• Carbon chains

– Form the skeletons of most organic molecules

– Vary in length and shape

HHH

HH

H H H

HH

H

H H H

H H HH H

H

H

H

H

H

H

HH

HH H H H

H HH H

H H H H

H H

H H

HHHH H

HH

C C C C C

C C C C C C C

CCCCCCCC

C

CC

CC

C

C

CCC

CC

H

H

H

HHH

H

(a) Length

(b) Branching

(c) Double bonds

(d) Rings

Ethane Propane

Butane 2-methylpropane(commonly called isobutane)

1-Butene 2-Butene

Cyclohexane Benzene

H H H HH

Figure 4.5 A-D


Hydrocarbons

• Hydrocarbons

– Are molecules consisting of only carbon and hydrogen


• Hydrocarbons

– Are found in many of a cell’s organic molecules

(a) A fat molecule (b) Mammalian adipose cells100 µm

Fat droplets (stained red)

Figure 4.6 A, B


Isomers

• Isomers

– Are molecules with the same molecular formula but different structures and properties


• Three types of isomers are

– Structural

– Geometric

– Enantiomers

H H H H HH

H H H H HH

HHH

HH

H

H

H

H

HHH

H

H

H

H

CO2H

CH3

NH2C

CO2H

HCH3

NH2

X X

X

X

C C C C C

CC

C C C

C C C C

C

(a) Structural isomers

(b) Geometric isomers

(c) Enantiomers

H

Figure 4.7 A-C


• Enantiomers

– Are important in the pharmaceutical industry

L-Dopa

(effective against Parkinson’s disease)

D-Dopa

(biologically inactive)Figure 4.8


• Concept 4.3: Functional groups are the parts of molecules involved in chemical reactions


The Functional Groups Most Important in the Chemistry of Life

• Functional groups

– Are the chemically reactive groups of atoms within an organic molecule


– Give organic molecules distinctive chemical properties

CH3

OH

HO

O

CH3

CH3

OH

Estradiol

Testosterone

Female lion

Male lionFigure 4.9


• Six functional groups are important in the chemistry of life

– Hydroxyl

– Carbonyl

– Carboxyl

– Amino

– Sulfhydryl

– Phosphate


• Some important functional groups of organic compounds

FUNCTIONALGROUP

STRUCTURE

(may be written HO )

HYDROXYL CARBONYL CARBOXYL

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–.)

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).

C

O O

COH

Figure 4.10

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



Acetic acid, which gives vinegar its sour tatste

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 group is at the end of the carbon skeleton

Carboxylic acids, or organic acids

EXAMPLE

Propanal, an aldehyde

Acetone, the simplest ketone

Ethanol, the alcohol present in alcoholic beverages

H

H

H

H H

C C OH

H

H

H

HH

H

HC C H

C

C C

C C C

O

H OH

O

H

H

H H

H O

H

Figure 4.10



FUNCTIONALPROPERTIES

Is polar as a result of the electronegative oxygen atom drawing electrons toward itself. Attracts water molecules, helping dissolve organic compounds such as sugars (see Figure 5.3).

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,

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

H

H

C

H

H

C

O

OH

H

H

C

O

C

O

+ H+

Figure 4.10



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

AMINO SULFHYDRYL PHOSPHATE

(may be written HS )

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 (—OPO3

2–) is an ionized form of a phosphoric acid group (—OPO3H2; note the two hydrogens).

NH

H

SHO P

O

OH

OH

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.

Glycine EthanethiolGlycerol phosphate

O

C

HO

C

HH

N

H

H

H

C C SH

H

H H

H

H

OH

C C C O P O

OHHH

OH OH

Figure 4.10



Acts as a base; can pick up a proton from the surrounding solution:

Ionized, with a charge of 1+, under cellular conditions.

(nonionized) (ionized)

N

H

H H

+N H

H

Two sulfhydryl groups can interact to help stabilize protein structure (see Figure 5.20).

Makes the molecule of which

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

Figure 4.10


The Chemical Elements of Life: A Review

• The versatility of carbon

– Makes possible the great diversity of organic molecules

04- carbon chemistry text

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