Chapter 18 Benzene Mechanisms

Benzenes & synthesis

Bromination

Reagent:

Br2 & AlBr3

chlorination

Reagent:

Cl2 & AlCl3

nitration

Reagent:

HNO3 & H2SO4

Reduction

Reagent:

1.) Fe, Zn, HCl & 2.) NaOH

sulfonation

fuming H2SO4

Desulfination

Starting product: benzene w/ SO3H

Dilute H2SO4

product: normal benzene

Friedel craft alkylation

Reagent:

CH3Cl & AlCl3

The Cl will get picked up by AlCl3

Oxidation

Reagent:

1.) KMnO4, H2O, Heat & 2.) H3O+

will produce COOH directly onto ring!

Friedel craft acylation

Clemmensen reduction

Reagent:

Zn(Hg), HCl & heat

intramolecular attack; form a ring

When the starting product contains an aromatic ring and an acyl halide, what is this called? What do we form?

Reagent: AlCl3

Strong activating groups

more than capable of donating electrons to ring instead of elsewhere

Moderate activating groups

less likely to donate electrons to the ring, but still can do so

Weak activating groups

can only donate electrons by inductive effect

Weak deactivating groups

ortho / para

Halides are considered deactivating groups, but they are _______ directors.

Moderately deactivating groups

strong deactivating groups

Activating groups

Which groups have para & ortho directors?

Deactivating groups

Which groups have meta directors?