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CHAPTER 1

Bonding and Isomerism

ATOMS and ELECTRONS

ATOMS = NUCLEUS and ELECTRONS

Protons, Neutrons, Atomic Number and Atomic Weight

Number and Arrangement of Electrons

Orbitals, Shells and Valence Electrons

p. 2, Table 1-1

p. 3, Table 1-2

p. 3, Table 1-3

p. 4a

IONIC BONDS

p. 6a

Covalent Bonds

p. 7a

Carbon and the Covalent Bond

p. 8a

Carbon-Carbon Single Bond

Bond Length and Bond Energy

p. 9a

Polar Covalent Bonds

p. 10

p. 11a

Multiple Covalent Bonds

Nonbonding Electrons vs Unshared Electron Pairs

p. 12a

Carbon-Carbon Covalent Bonds

p. 12, Table 1-5

Valence

Number of bonds an atom can form

p. 13

Possible Structures for C3H4 with Correct Valences

p. 14

Isomers

Isomer =

p. 15a

Writing Structural Formulas

Structural Formulas for C5H12

First write all carbon atoms in a continuous chainThen add hydrogen atoms

p. 15b

Next, consider branched chain of carbon atoms

p. 15d

Problems with Chains!

p. 15e

One more branched chain structure

p. 16b

To which isomer of C5H12 does each of the following belong?

p. 16c

Abbreviated Structural Formulas

p. 17a

OR

Abbreviated Structures for the 3 Pentane Isomers

Use Lines to Represent Carbon Framework

p. 18c

Another Example

p. 18f

Formal Charge Or where charge is located in a multi-atom ion or molecule

FC = # valence electrons in neutral atom - (# unshared electrons + half # shared electrons)

For water and hydronium ion, what is the formal charge on: a. hydrogen b. oxygen

p. 19a

Which atom contains formal charge?

What is the formal charge on nitrogen in: a. ammonia (NH3) b. ammonium ion (NH4

+) c. amide ion (NH2

-)

p. 20a

Resonance

p. 21b

Arrow Formalism

Curved Arrow: how electrons are moved during reactions and in resonance structures

Double Headed Arrow: indicates resonance structures

p. 22b

Single Headed Straight Arrow: point from reactants to products of a reaction

Arrows with Half a Head (Fishhook):indicate movement of single electron

p. 23, Fig. 1-2

Orbital View of Bonding: The Sigma Bond

Shapes of Orbitals

p. 23, Fig. 1-3

Atomic to Molecular OrbitalsMolecular Orbital Representation Covalent Bond Formation

s-s molecular orbital called a sigma orbital the bond is called a sigma bond

Sigma bond formation from s-atomic orbitals

p. 24, Fig. 1-4

Sigma bonds using p-atomic orbitals

p. 23

Two properly aligned p-atomic orbitals formanother type of covalent bond called a pi bond

p. 24, Fig. 1-5

Orbitals and Covalent Bonding with Carbon Atoms

p. 24, Fig. 1-6

Formation of sp3 Hybrid Orbitals on Carbon

sp3 orbital is 25% s and 75% p

p. 25, Fig. 1-7

An sp3 hybrid orbital 4 sp3 orbitals on a carbon atom

p. 25, Fig. 1-8

Sigma bonds using sp3 hybrid orbitals

p. 25, Fig. 1-9

Tetrahedral Carbon; Bonding in Methane

p. 26, Fig. 1-10

p. 26, Fig. 1-11

p. 27a

Classification According to Carbon Skeleton

Acyclic Compounds

p. 28, Fig. 1-13a

Carbocyclic Compounds

p. 29, Fig. 1-14

Heterocycle Compounds

p. 30, Table 1-6a

Classification According to Functional GroupFunctional Group =

p. 31, Table 1-6b