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Question:

(a) Write the mechanism of the following reaction: 2CH3CH2OH + H+ → CH3CH2OCH2CH3 (b) Write the equation involved in the acetylation of salicylic acid

Solution:

(a) The reaction is an acid-catalyzed dehydration of ethanol to diethyl ether. The mechanism involves the following steps:

Step 1: Protonation of ethanol

A proton from the acid catalyst (H+) adds to the oxygen atom of ethanol, making it a better leaving group.

CH3CH2OH + H+ → CH3CH2OH2+

Step 2: Nucleophilic attack

The oxygen atom of a second ethanol molecule acts as a nucleophile and attacks the carbon atom bearing the protonated hydroxyl group. This forms a new C-O bond.

CH3CH2OH + CH3CH2OH2+ → CH3CH2OCH2CH3 + H2O

Step 3: Deprotonation

A base (water or another ethanol molecule) abstracts a proton from the protonated ether, resulting in the formation of diethyl ether and regeneration of the acid catalyst.

CH3CH2OCH2CH3 + H2O → CH3CH2OCH2CH3 + H3O+

(b) Acetylation of salicylic acid involves the reaction of salicylic acid with acetic anhydride (or acetyl chloride) in the presence of a catalyst (usually a base like pyridine). The reaction forms acetylsalicylic acid (aspirin) and acetic acid (or HCl).

The equation is:

HO-C6H4-COOH + (CH3CO)2O → CH3COO-C6H4-COOH + CH3COOH