(a) Mechanism of the reaction between ethanol and HBr:
Step 1: Protonation of the hydroxyl group
The oxygen atom in the hydroxyl group of ethanol has lone pairs of electrons. These lone pairs can attack the proton (H+) from the HBr molecule. This step protonates the hydroxyl group, making it a better leaving group.
CH3CH2OH + HBr ⇌ CH3CH2OH2+ + Br-
Step 2: Formation of a carbocation
The protonated hydroxyl group (-OH2+) is a good leaving group and departs from the molecule, leaving behind a carbocation.
CH3CH2OH2+ → CH3CH2+ + H2O
Step 3: Nucleophilic attack
The bromide ion (Br-), which is a nucleophile, attacks the carbocation, forming a new carbon-bromine bond.
CH3CH2+ + Br- → CH3CH2Br
Overall reaction:
CH3CH2OH + HBr → CH3CH2Br + H2O
(b) Reimer-Tiemann Reaction:
The Reimer-Tiemann reaction is an example of electrophilic aromatic substitution. It involves the ortho-formylation of phenols using chloroform (CHCl3) in the presence of a strong base, usually aqueous NaOH. The reaction proceeds through the formation of a dichlorocarbene intermediate.
The overall equation is:
C6H5OH + CHCl3 + 3NaOH → C6H4(OH)CHO + 3NaCl + 2H2O
where C6H5OH represents phenol and C6H4(OH)CHO represents salicylaldehyde (ortho-hydroxybenzaldehyde).