Match the LIST-I with LIST-II.
| LIST-I Reaction | LIST-II Reagent |
| A. Rosenmund reaction | I. SnCl2, HCl |
| B. Stephen reaction | II. H2 , Pd-BaSO4 |
| C. Etard reaction | III. CrO2Cl2 , CS2 , H3O+ |
| D. Friedel-Crafts reaction | IV. Anhyd. AlCl3 |
Choose the correct answer from the options given below:
Answer & explanation
Correct answer: option 1
The correct answer is Option (1) → A-II, B-I, C-III, D-IV
The named reactions in this list make aldehydes and ketones. They can be recognised from the starting material and the reagent:
From acid derivatives (reduction): Rosenmund reduction — acyl chloride + H2, Pd-BaSO4 gives an aldehyde; Stephen reaction — nitrile + SnCl2, HCl, then hydrolysis, gives an aldehyde (DIBAL-H does the same change for nitriles and esters).
From hydrocarbons (oxidation of a methyl group): Etard reaction — toluene + chromyl chloride (CrO2Cl2) in CS2, then hydrolysis, gives benzaldehyde; Gattermann–Koch reaction — benzene + CO and HCl with anhydrous \( \ce{AlCl3} \)/CuCl gives benzaldehyde.
Acylation of arenes: Friedel–Crafts acylation — benzene + acyl chloride with anhydrous AlCl3 gives an aromatic ketone.
A. Rosenmund reaction — This matches II. H2 , Pd-BaSO4. The acyl chloride is hydrogenated over palladium on barium sulphate; the catalyst is partially poisoned so that reduction stops at the aldehyde.
\( \displaystyle \ce{R-COCl + H2} \xrightarrow{\ce{Pd-BaSO4}} \ce{R-CHO + HCl} \)
B. Stephen reaction — This matches I. SnCl2, HCl. The nitrile is reduced by stannous chloride and HCl to an imine, which is hydrolysed to the aldehyde.
\( \displaystyle \ce{R-CN} \xrightarrow{\ce{SnCl2},\ \ce{HCl}} \ce{R-CH=NH} \xrightarrow{\ce{H3O^+}} \ce{R-CHO} \)
C. Etard reaction — This matches III. CrO2Cl2 , CS2 , H3O+. Chromyl chloride oxidises the methyl group of toluene to a chromium complex, which is hydrolysed to benzaldehyde.
\( \displaystyle \ce{C6H5-CH3} \xrightarrow[\ce{H3O^+}]{\ce{CrO2Cl2},\ \ce{CS2}} \ce{C6H5-CHO} \)
D. Friedel-Crafts reaction — This matches IV. Anhyd. AlCl3. The Lewis acid AlCl3 generates the acylium ion from the acyl chloride, which attacks the benzene ring to give a ketone.
\( \displaystyle \ce{C6H6 + CH3COCl} \xrightarrow{\text{anhyd. }\ce{AlCl3}} \ce{C6H5-CO-CH3 + HCl} \)
Shortcut: The pair A–II appears only in Option (1).