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Question of 87

Q.Write short notes on the following:

(a) Clemmensen reduction
(b) Wurtz reduction
(c) Hell-Volhard-Zelinsky reaction OR Identify 'X', 'Y' and 'Z' in the following:
(a) CH3COOH --(NH3, Heat, -H2O)--> 'X' --(Br2/KOH)--> 'Y'
(b) CH3COCH3 --(LiAlH4)--> 'X' --(H2SO4 conc., Heat)--> 'Y'
(c) Bromobenzene (a benzene ring with a -Br substituent) --(Mg/dry ether)--> 'Z'
Jharkhand JacJAC Intermediate Board 2020Subjective· 5mImportance★★★★★
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All three are named reactions used to build or transform carbon skeletons: Clemmensen strips a carbonyl down to CH2, Wurtz couples two haloalkanes into one longer alkane, and HVZ installs a halogen next to a carboxylic acid's -COOH group.

  1. Clemmensen reduction: An aldehyde or ketone's carbonyl group (C=O) is fully reduced to a methylene group (CH2) by treating it with zinc amalgam (Zn-Hg) and concentrated hydrochloric acid, under reflux: R-CO-R' --(Zn-Hg / conc. HCl)--> R-CH2-R' This is especially useful for aromatic ketones (e.g., converting an acyl-substituted benzene, made by Friedel-Crafts acylation, into the corresponding alkylbenzene), since it works under strongly acidic conditions (unlike Wolff-Kishner, which is base-mediated and preferred for acid-sensitive substrates).
  2. Wurtz reaction: Two molecules of an alkyl halide react with sodium metal in dry ether to couple together, forming a higher alkane with twice the carbon count (when both halide molecules are identical) and releasing NaX: 2 R-X + 2Na --(dry ether)--> R-R + 2NaX It is mainly useful for making symmetrical alkanes with an even number of carbon atoms. …

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