The REIMER-TIEMANN reaction converts phenol to salicylaldehyde. The reagents are
A$\mathrm{HCHO} + \mathrm{HCl}$
B$\mathrm{CHCl_3} + \mathrm{NaOH}$
C$\mathrm{CO_2} + \mathrm{NaOH}$
D$\mathrm{Cl_2} + \mathrm{H_2O}$
Answer & Solution
Correct answer: B. $\mathrm{CHCl_3} + \mathrm{NaOH}$
1. Your syllabus: Reimer-Tiemann introduces a $\mathrm{-CHO}$ group at the ORTHO position of phenol.
2. REAGENTS: chloroform ($\mathrm{CHCl_3}$) and aqueous NaOH, followed by acid workup.
3. Mechanism: NaOH deprotonates $\mathrm{CHCl_3}$ to $\mathrm{CCl_3^-}$, which loses a chloride to generate a DICHLOROCARBENE ($\mathrm{:CCl_2}$).
The carbene attacks the ortho position of the phenoxide ion.
Hydrolysis of the resulting dichloro group gives the aldehyde.
4. Product: ortho-hydroxybenzaldehyde (SALICYLALDEHYDE).
5. Option A would be a Mannich-style attempt. Option C is the KOLBE reaction (which gives salicylic ACID, not salicylaldehyde). Option D is chlorination of phenol (different product).
_Source: syllabus Chemistry Part 2, Ch 7, §7.7 (Phenol reactions — Reimer-Tiemann), p. 18–19._
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