AROMATIC SULFONATION

Aromatic rings can be sulfonated by reaction with fuming sulfuric acid, a

mixture of H2SO4 and SO3.

The reactive electrophile is either HSO3+ or neutral SO3, depending on

reaction conditions, and substitution occurs by the electrophilic two-step
mechanism.

Sulfonation reaction is readily reversible; it can occur either forward or

backward depending on the reaction conditions.

Sulfonation is favored in strong acid, but desulfonation is favored in hot,

dilute aqueous acid.
The electrophilic substitution mechanism

Step 1

Step 2
AROMATIC SULFONATION CONT

Benzene attack sulphur trioxide, forming a sigma complex.

Loss of proton on tetrahedral carbon and reprotonation of

oxygen gives benzenesulfonic acid.
AROMATIC DESULFONATION
AROMATIC DESULFONATIONCONT
 ALCOHOL
Alcohol from reduction of carbonyl compounds (Aldehyde).
Aldehydes are easily reduced to yield alcohols.
Aldehydes are converted into primary alcohols.

Many reagents are used to reduce aldehydes to alcohols, but lithium

aluminium hydride in dry ether followed by hydrolysis is usually
chosen.
 ALCOHOLCONT
Alcohol from reaction of aldehyde with Grignard reagents.
A Grignard reagents has a formula RMgX where X is halogen, and R is
alkyl or aryl (based on a benzene ring) group.

A typical
Grignard reagent
might be
CH3CH2MgBr.
 ALCOHOLCONT
The reaction between Grignard reagents and methanal

In methanal, both R groups are hydrogen.

Methanal is the simplest possible aldehyde.

Assuming that you are starting with CH3CH2MgBr and using the
general equation before, the alcohol you get always has the form;
 ALCOHOLCONT
The reaction between Grignard reagents and methanal

Since both R groups are hydrogen atoms, the final product will be:

A primary alcohol is formed. A primary alcohol has only one alkyl group
attached to the carbon atom with the OH group on it.

You could obviously get a different primary alcohol if you started from
different Grignard reagent.
 ALCOHOLCONT
The reaction between Grignard reagents and ethanal

As for ethanal one of the R groups is hydrogen and the

other CH3.

So this time the final product has one CH3 group and
one hydrogen attached:

A secondary alcohol has two alkyl groups attached to the carbon

with the OH group on it.
 ALCOHOLCONT
Oxidation of alcohols

Primary and secondary alcohols are oxidized to aldehydes and

ketones respectively.
Tertiary alcohols are stable to undergo oxidation.
In the case of primary alcohols, the final product could be carboxylic
acid as aldehyde can be oxidized further.
 Acid catalyzed condensation of
alcohols