Match List - I with List - II.
| List I | List II |
| (A) Williamsons Synthesis | (I) \(C_6H_5Cl + NaOH \underset{\text{high P}}{\overset{350^oC}{\longrightarrow}}\) |
| (B) Reimer Tiemann reaction | (II) \(C_6H_5OH + C_6H_5COCl \overset{\text{aq. NaOH}}{\longrightarrow}\) |
| (C) Dow's Process | (III) \(CH_3CH_2ONa + CH_3Cl \overset{\text{heat}}{\longrightarrow}\) |
| (D) Schotten Baumann reaction | (IV) \(C_6H_5OH + CHCl_3 + NaOH \overset{heat}{\longrightarrow}\) |
Choose the correct answer from the options given below:
Answer & explanation
Correct answer: option 1
The correct answer is Option (1) → (A)-(III), (B)-(IV), (C)-(I), (D)-(II)
These are the named reactions used to make and use phenols and ethers: Williamson synthesis (alkyl halide + sodium alkoxide → ether), Dow’s process (chlorobenzene + NaOH at high temperature and pressure → phenol), Reimer-Tiemann reaction (phenol + \( \ce{CHCl3} \)/NaOH → salicylaldehyde) and Schotten-Baumann reaction (benzoylation of a phenol or amine with benzoyl chloride in aqueous NaOH).
(A) Williamsons Synthesis — This matches (III) CH3CH2ONa + CH3Cl, heat. The alkoxide ion attacks the primary alkyl halide (SN2) and gives an ether:
\( \ce{CH3CH2ONa} \) + \( \ce{CH3Cl} \) → \( \ce{CH3CH2OCH3} \) + NaCl
(B) Reimer Tiemann reaction — This matches (IV) C6H5OH + CHCl3 + NaOH, heat. A –CHO group is introduced at the ortho position of phenol:
\( \ce{C6H5OH} \) + \( \ce{CHCl3} \) + aq. NaOH → o-\( \ce{HOC6H4CHO} \) (salicylaldehyde, after acidification)
(C) Dow’s Process — This matches (I) C6H5Cl + NaOH, 350°C, high P. Chlorobenzene fused with NaOH at about 623 K and high pressure gives sodium phenoxide, which on acidification gives phenol:
\( \ce{C6H5Cl} \) + 2NaOH → \( \ce{C6H5ONa} \) + NaCl + \( \ce{H2O} \); \( \ce{C6H5ONa} \) + HCl → \( \ce{C6H5OH} \) + NaCl
(D) Schotten Baumann reaction — This matches (II) C6H5OH + C6H5COCl, aq. NaOH. The phenol is benzoylated to an ester; the NaOH removes the HCl formed:
\( \ce{C6H5OH} \) + \( \ce{C6H5COCl} \) → \( \ce{C6H5OCOC6H5} \) (phenyl benzoate) + HCl
Shortcut: (A)-(III) appears only in Option (1).