Chapter 1 Structure and Bonding

I. What is Organic Chemistry?

A. Organic Chemistry = chemistry of carbon containing (organic) molecules

B. Most Familiar compounds are “organic”

1) Cotton in clothing 4) Plastics
2) Gasoline 5) Drugs
3) Food 6) Dyes

C. Natural Products vs. Synthetic Organic compounds

1) Natural Products are compounds we find in the environment
a) May need to be refined or isolated from the source
b) Are starting materials for synthetic compounds
2) Synthetic Organic compounds do not occur naturally and must be
O
synthesized from simpler compounds CH3
CH3 N
N

D. Caffeine: an important organic molecule O N N

CH3
 In 1998, Americans guzzled 15 billion gallons of soda, an average of about
585 cans per person.

Caffeine in sodas aims to addict, study suggests

Researchers draw comparison to nicotine’s use in cigarettes
MSNBC Staff and Wire Reports 8/15/00
Caffeine in soft drinks — which Americans drink more of
than water — is added to addict consumers, not to
enhance flavor as soft drink manufacturers claim, said
researchers who compared caffeine’s use in sodas to
nicotine in cigarettes.

Select an addictive substance from the menu below to read about the
psychological and physical effects each drug has on the human body.
Source: 'Principles of Addiction Medicine', 1994

Caffeine is the world’s most widely consumed and only entirely unregulated
psychoactive agent. It works by blocking a sedating compound in the brain.
Blood levels peak within 30 to 45 minutes, and withdrawal symptoms --
including headache, fatigue and an inability to concentrate -- set in after 12 to 24
hours. About 10 percent of the population develops a dependence syndrome
called caffeinism, which is indistinguishable from panic disorder or general
anxiety. The more caffeine you consume, the more likely you are to use anti-
anxiety medications. Fatal oral overdoses are extremely rare, requiring the
consumption of 50 to 100 cups of regularly brewed coffee.

http://www.msnbc.com/news/446035.asp?bt=nm&btu=http://www.msnbc.com/tools/newstools/d/news_menu.asp&cp1=1
 Course Overview
II. How will we study Organic Chemistry
A. Relationship of a molecule’s Structure with its Reactivity

B. Functional Group = a group of atoms that controls a molecule’s reactivity

1) Method of classifying organic molecules
2) Similar reactivity for compounds having the same functional group
O
CH3CH2CH2CH2CH3 CH3CH2CH2CH2OH
CH3CH2CH2CH2COCH3
Alkane Alcohol Ester

C. Nomenclature = systematic naming of organic compounds

D. Reactivity
1) How to synthesize a functional group
2) The reactions a functional group can undergo
3) Mechanism = detailed intermediate steps in a reaction
 Course Overview 2

Text: Reactions are like Words Need Both to

Mechanisms are like Grammar “Speak” Organic Chemistry

E. Stereochemistry = exact arrangement in space of the atoms in a molecule

H H
C C
I Cl F
F Cl
I

F. Synthesis = making molecules from simpler starting materials

O O
CH3CH2CH2CH2COH + HOCH3 CH3CH2CH2CH2COCH3
 Simple Bonding
III. Coulomb Forces as a Simple Bonding Model
A. Chemical Bond = energetically favorable interaction of 2 atoms which holds
them together at a defined distance from each other
1) Energy (heat) is released as 2 atoms come together to form a bond (energy
input is required to break a chemical bond)
a) Opposite charges attract
b) Electrons spread out to fill a defined space

Covalent Bond =
shared electrons

Ionic Bond =
transferred electrons
B. Coulomb’s Law is a basis for chemical bonding

 [  ]  [ ] 
F  c 
 d 
2

Bond Length = distance between nuclei at minimum energy

IV. The Octet Rule
A. Periodic Table Review

1) Atomic Number = # of protons = # of electrons in neutral atom

2) Electron Shells: 2, 8, 18, …
3) Valence Shell = outermost shell
a) Filled electron shells are energetically desirable so atoms react
accordingly
b) Noble gases (He, Ne, Ar, Kr, Xe) have filled shells, are unreactive
c) Duet important for H, He
d) Octet important for C, N, O, …
B. Pure Ionic Bonds
1) Transfer of valence electrons from one neutral atom to another creates a
cation and and anion and forms an ionic bond

2) Ionization Potential = energy input to remove an electron

Na Na+ + e- DE = 119 kcal/mol

3) Electron Affinity = energy released upon binding an electron

Cl + e- Cl- DE = -83 kcal/mol

4) Formation of an Ionic Bond

Na + Cl Na+Cl- Ionization Potential = +119 kcal/mol

Electron Affinity = -83 kcal/mol
Coulomb Attraction = -120 kcal/mol
Total DE = -84 kcal/mol
C. Electron Dot Notation
1) Core Configuration: Atomic symbol = nucleus + inner shell electrons
2) Valence Electrons: represented by dots around the core

Na + Cl Na Cl

3) Types of Hydrogen
a) Hydrogen atom H
b) Proton
H
c) Hydride H

D. Covalent Bonds
1) Sharing Electrons to reach octet configuration forms a bond
2) Why aren’t all bonds ionic?

2H H H DE = +300 kcal/mol

4+ 4-
2 C C C DE = Very Large
 3) Sharing reduces charge and maximizes e- exchange
2H H H = H H
= = single bond
H + Cl H Cl = H Cl
H
H H H = = double bond
3H + N NH HNH = H N H
H H H = = triple bond
H H H H
2 HC C C = C C
H H H H
4) Unequal Sharing gives Polar Covalent Bonds
a) Electropositive = electron donating atoms (Na, K, left side of P.T.)
b) Electronegative = electron accepting atoms (Cl, N, O, right side P.T.)

H
2.2
Li Be B C N O F
1.0 1.6 2.0 2.6 3.0 3.4 4.0
Na Mg Al Si P S Cl
0.9 1.3 1.6 1.9 2.2 2.6 3.2
K Br
0.8 3.0
c) Ionic Bonds form between extremes

Na + Cl Na Cl

d) Covalent Bonds form between like electronegativities

2H H H = H H

H + Cl H Cl = H Cl

e) A Polar Covalent Bond is one between unequal electronegativities

- - 
+
F
+
 H
H2N CH3
f) Symmetry can cancel out the dipole moment for the whole molecule
even if the individual bonds are polar
-

Cl
- + 
-

-
+ -
Cl C Cl 
O C O
Cl-

 VSEPR Theory
E) Valence Shell Electron Pair Repulsion: VSEPR
1) Shape of molecules is determined by repulsion between valence electrons
a) Diatomic molecules are linear

H Cl = H Cl Linear

b) Triatomic molecules can be linear or bent

F Be F = F Be F
Linear
180o
c) AB3 molecules
Cl Cl
B Cl = B Cl Trigonal
Cl Cl 120o
d) AB4 molecules
F
F F
109.5o Tetrahedral
FCF = C
F F F