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The Star of The Show(Ch.

4)
#5alldayerrday

Organic versus Inorganic Molecules


Contains Carbon
Large covalent molecules
Plays a role in living things,
necessary element of life

Does not contain Carbon


Smaller ionic molecules

Why study Carbon?


All of life is built on carbon
Backbone of Biological Molecules
Cells
~72% H2O
~25% carbon compounds

carbohydrates
lipids
proteins
nucleic acids

~3% salts

Na, Cl, K

Chemistry of Life
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
Ball-andName and
Comments

Molecular Structura
Formula l Formula

(a) Methane

CH4

(b) Ethane

C2H
6

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

C2H
4

H
H C H
H
H H
H C C H
H H
H
H

C C

H
H

Stick
Model

SpaceFilling
Model

The bonding versatility of carbon allows it


to form many diverse molecules,
including carbon skeletons
Name and
Comments
(a) Methane

Molecular Structural
Formula Formula
H

CH4

H C

(b) Ethane

C2H

H H
H C C H

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

C2H4

H H
H
H

C C

H
H

Ball-andStick
Model

SpaceFilling
Model

The electron configuration of carbon gives it covalent


compatibility with many different elements
Carbon has four valence electrons and
may form single, double, triple, or quadruple bonds
Can form FOUR stable covalent bonds at same time
(=tetravalence)
Common partners = O, H, N [4 main CHON]

TETRAVALENCE makes large complex


molecules with a variety of shapes possible

Carbon may bond to itself forming carbon


chains
Carbon chains vary in length and shape

ure 4.5 A-D

(a) Length

H H
Ethane

H H
Propane
H

(b) Branching

H
H

H
H

Butane

(c) Double bonds

isobutane

1-Butene
(d) Rings

H
H
H
H

H
C
C

C
C

H
C
C

H
H
H
H

Cyclohexane

H
2-Butene
H

C
C

C
C

Benzene

Hydrocarbons
Hydrocarbons are molecules consisting of only carbon
and hydrogen. Hydrocarbons are found in many of a
cells organic molecules. Major component of petroleum
(aka fossil fuel). Ex. fats
Covalent bonding; nonpolar
High energy storage

Isomers
Molecules with same molecular formula but
different structures (shapes)
different chemical properties
different biological functions

6 carbons
6 carbons
6 carbons

Isomer Types
-Structural
-Geometric
-Enantiomers

STRUCTURAL isomers

differing covalent bonding arrangement

C6H12O6

C6H12O6

C6H12O6

GEOMETRIC isomers - differ in


arrangement around a DOUBLE BOND

trans- form

cis- form

ENANTIOMER isomers - differ in


arrangement around a ASYMMETRIC
carbon

. . . Mirror images

Form/Structure affects function


Structural differences create important functional
differences
Two molecules can have the same amount of atoms but
different structures would result in different functions
Thalidomide
prescribed to pregnant women in 50s & 60s
reduced morning sickness, butcaused severe birth defects

Importance of Structure

Functional groups
They are the chemically reactive groups of
atoms within an organic molecule
Give organic molecules distinctive chemical
properties
give organic molecules distinctive properties
hydroxyl
carbonyl
carboxyl

amino
sulfhydryl
phosphate

Affect reactivity
increase solubility in water

Methyl group not reactive, used as a tag on


biological molecules

Importance of Functional groups


Basic structure of male and female hormones are
identical
Identical C skeleton
Attachment of different functional groups
Interact with different targets in the body

Hydroxyl
OH or HO-

Polar due to O, attract water molecules


which help dissolve compounds like sugars
organic compounds with OH = alcohols
names typically end in -ol
Ethanol

Carbonyl
C=O

Examples: acetone and propanal


Found in sugars
O double bonded to C
if C=O at end molecule = aldehyde, end in -al
if C=O in middle of molecule = ketone, end in-one

Carboxyl
COOH
C double bonded to O & single bonded to OH
group
compounds with COOH = acids, ends in-oic
fatty acids
amino acids

Amino

-NH2
N attached to 2 H
compounds with NH2 = amines or amino,-ine
amino acids

NH2 acts as base


ammonia picks up H+ from solution

Sulfhydryl

SH or HS S bonded to H
compounds with SH = thiols
SH groups stabilize the structure of proteins by
building protein bridges, ex. Curly hair

Phosphate

PO4, polar, acid, hydrophilic


P bound to 4 O
connects to C through an O
lots of O = lots of negative charge
highly reactive

transfers energy between


organic molecules
ATP, GTP, etc.

Methyl
-CH3, nonpolar/hydrophobic
Can be attached to carbon or to different atom
Addition of methyl group to DNA, affects gene
expression of genes
Arrangement of methyl groups in male and
female sex hormones affect shape and function

Organic Compounds
Organic compounds often form Polymers
Long chains of smaller molecules called
monomers, bind to form huge macromolecules
4 Types: Carbohydrates, Lipids, Proteins, and
Nucleic Acids

What are the Functional Groups?


H
O

H
H

OH

OH

OH

OH

A. ROH

B. R=O

C. R-COOH

D. R-SH

E. R-PO4

R = organic compound

1. Produces hydronium ions in water (C)


2. Placement determines whether the
molecule is an aldehyde or a ketone (B)
3. Contains the major high energy bond in
biological molecules (E)
4. Used in proteins to stabilize structure (D)
5. Presence of this group classifies molecules
as alcohols. (A)