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I. PhCH3i. CrO2Cl2−−−−−−ii. H+/H2O

II. PhCCl3KOH−−excess

III. PhCH2OHPCC−−

IV. PhO||CClH2−−−−−−PdBaSO4

V. PhCNi. SnCl2/HCl−−−−−−−ii. H+/H2O

VI. PhHCO/HCl−−−−−−−anhyd. AlCl3

VII. PhHCH3Cl−−−−−−−anhyd. AlCl3H+,KMnO4−−−−−−Δ

Consider following reactions and give the number of reactions which prooduce benzaldehyde as final major product.


Solution

I. Etard's Reaction
 PhCH3i. CrO2Cl2−−−−−−ii. H+/H2OPhCHO

II. PhCCl3KOH−−excessPhCOOK

III. PhCH2OHPCC−−PhCHO

IV. Rosenmund reaction
 PhO||CClH2−−−−−−PdBaSO4PhCHO

V. Stephen's reaction
PhCNi. SnCl2/HCl−−−−−−−ii. H+/H2OPhCHO

VI. Gattermann Koch reaction
 PhHCO/HCl−−−−−−−anhyd. AlCl3PhCHO

VII. Friedel-Crafts alkylation followed by oxidation
 PhHCH3Cl−−−−−−−anhyd. AlCl3PhCH3H+,KMnO4−−−−−−ΔPhCOOH

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