ChemistryNEB 2076 (old course)

Identify the major products A and B giving their IUPAC names in the given reaction sequence. Methoxy methane [ ]excess HI A Sodium phenoxide B

2

Answer

CH3OCH3methoxy methane+2HIexcess HI, ΔCH3I+CH3OH
Step 1: Cleavage of methoxy methane (CH₃OCH₃) by HI to form iodomethane (CH₃I) and methanol (CH₃OH)
  1. Reaction with excess HI: Methoxy methane () undergoes cleavage with excess HI to form iodomethane () as the major product (IUPAC name: methanamine is incorrect; the correct product is iodomethane). The reaction proceeds via an mechanism, breaking the C–O bond and replacing the methoxy group with iodide.
MethylamineMethylamine
Structure of Methylamine
  1. Reaction with sodium phenoxide: reacts with sodium phenoxide () in a nucleophilic substitution to form phenol methyl ether () as product (IUPAC name: methoxybenzene).
CH3I+C6H5ONanucleophilic substitutionanisoleanisole+NaI
Step 2: Reaction of iodomethane (CH₃I) with sodium phenoxide (C₆H₅ONa) to form anisole (C₆H₅OCH₃) and sodium iodide (NaI)

Final Products:

  • : Iodomethane ()
  • : Methoxybenzene ()

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