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Question 43 of 66

Q.Write the following reactions :

(i) Clemmenson reduction
(ii) Perkins reaction
Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2017Subjective· 5mImportance★★★★★
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Clemmensen reduction converts a carbonyl (aldehyde/ketone) directly to a methylene (−CH2−-CH_2-) group with Zn(Hg)Zn(Hg)/conc. HCl; the Perkin reaction condenses an aromatic aldehyde with an aliphatic acid anhydride, using the sodium salt of the same acid as catalyst, to build a cinnamic-acid-type α,β\alpha,\beta-unsaturated acid.

  1. Clemmensen reduction An aldehyde or ketone is refluxed with zinc amalgam, Zn(Hg)Zn(Hg), and concentrated hydrochloric acid. The carbonyl oxygen is completely removed and replaced by two hydrogen atoms, so C=OC=O is converted straight to CH2CH_2: R2C=O→conc. HCl, ΔZn(Hg)R2CH2+H2OR_2C=O \xrightarrow[conc.\,HCl,\ \Delta]{Zn(Hg)} R_2CH_2 + H_2O Example — acetophenone is reduced to ethylbenzene: C6H5COCH3→conc. HClZn(Hg)C6H5CH2CH3C_6H_5COCH_3 \xrightarrow[conc.\,HCl]{Zn(Hg)} C_6H_5CH_2CH_3 Because the reagent is strongly acidic, Clemmensen reduction is used only for substrates that are stable under acidic conditions; acid-sensitive molecules are instead reduced by the base-catalysed Wolff–Kishner method (hydrazine/KOH).
  2. Perkin reaction …

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