Chem Introduction Part 1

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Introduction

Organic Chemistry
The chemistry of the compounds of carbon
The human body is largely composed of organic
compounds
Organic chemistry plays a central role in medicine,
bioengineering etc.

Vitalism
Organic compounds could be made only by living things by
intervention of a vital force
Fredrich Whler disproved vitalism in 1828

CRITERIA

INORGANIC

ORGANIC

1. Elements involved

All of the elements

Relatively few elements


(mainly C, H, N, O, S, P, X)

2. Type of bonding
- within a unit
- between units

Mostly ionic
Mostly electrostatic

Covalent
Dispersion forces, dipoledipole, H-bonding

Ions

Molecules

Generally fast
Very fast

Generally slow
Moderately fast to explosive

sometimes

Often

6. Side reactions

None, many are quantitative

Yes, nearly always

7. combustibility

Non-combustible

Usually combustible

Mostly soluble
Insoluble
Yes
Relatively high
High
Nonvolatile

Mostly insoluble
Mostly soluble
No
Relatively low
Low
Usually volatile

3. Units of structure

4. Rates of reaction
- at room temperature
- at higher
temperature
5. Catalyst requirement

8. Physical properties
- solubility
-- in water
-- in organic
solvents
- electrical conduction
- melting point
- boiling point
- volatility

Structural Theory
Central Premises
Valency: atoms in organic compounds form a fixed
number of bonds (covalency number)

Carbon can form one or more bonds to other carbons

Isomers
Isomers are different molecules with the same molecular
formula
Many types of isomers exist
Example
Consider two compounds with molecular formula C2H6O
These compounds cannot be distinguished based on molecular
formula; however they have different structures
The two compounds differ in the connectivity of their atoms

Three Dimensional Shape of Molecules


Virtually all molecules possess a 3-dimensional shape
which is often not accurately represented by drawings

Chemical Bonds:
Octet Rule
Electronegativity
Electronegativity is the ability of an atom to attract electrons
It increases from left to right and from bottom to top in the periodic table
(noble gases excluded)

Fluorine is the most electronegative atom and can stabilize excess electron density the best

Writing Lewis Structures


Atoms bond by using their valence electrons
The number of valence electrons is equal to the group
number of the atom

Carbon is in group 4A and has 4 valence electrons


Hydrogen is in group 1A and has 1 valence electron
Oxygen is in group 6A and has 6 valence electrons
Nitrogen is in group 5A and has 5 valence electrons

To construct molecules the atoms are assembled with


the correct number of valence electrons
If the molecule is an ion, electrons are added or
subtracted to give it the proper charge
The structure is written to satisfy the octet rule for each
atom and to give the correct charge
If necessary, multiple bonds can be used to satisfy the
octet rule for each atom

Chapter 1

Propane (C3H8)

Acetylene (C2H2)

Ethanol (C2H5OH)

Acetone (C3H6O)

Try these

Acetonitrile (CH3CN)

Acetic acid (C2H4O2)

Formal charge
A formal charge is a positive or negative charge on
an individual atom
The sum of formal charges on individual atoms is
the total charge of the molecule or ion
The formal charge is calculated by subtracting the
assigned electrons on the atom in the molecule
from the electrons in the neutral atom
Electrons in bonds are evenly split between the
two atoms; one to each atom
Lone pair electrons belong to the atom itself

Ethene (C2H4)

Aminomethane (CH3NH2)

Methaniminium

Ethyl acetate

Try these

Nitromethane

A Summary of Formal Charges

Representing Organic Compounds

1) Molecular Formula

C2H6O

Ethanol/ethyl alcohol

2) Lewis Dot Structures

3) Condensed structures

CH3OH

CH3CH2OH

Representing Organic Compounds


4) Dash Structural Formula

- using lines to show covalent bonds

Representing Organic Compounds

5) Bond Line Structural Formula

line structures:
each intersection is a carbon
H on carbon is invisible assume carbons are saturated

line structure:

Br

Cl

Representing Organic Compounds

6) 3D Structural Formula

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