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Making Ethers - Alkoxymercuration definitions

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  • Alkoxymercuration
    A synthesis method for ethers where alcohol acts as the nucleophile, following a mechanism similar to oxymercuration.
  • Oxymercuration
    A reaction mechanism where water is the nucleophile, leading to alcohol formation via a mercury-bridged intermediate.
  • Ether
    A compound featuring an oxygen atom bonded to two alkyl or aryl groups, produced here by using alcohol as the nucleophile.
  • Nucleophile
    A species, such as alcohol or water, that donates an electron pair to form a new chemical bond during the reaction.
  • Markovnikov Site
    The position on an alkene where the nucleophile adds, characterized by greater positive character and stability.
  • Mercury Bridge
    An intermediate structure where mercury forms partial bonds with two carbons, stabilizing the positive charge.
  • Reduction Step
    A process using NaBH4 and OH- to replace mercury with hydrogen and deprotonate oxygen, finalizing ether formation.
  • NaBH4
    A reducing agent used to convert the mercury intermediate into a hydrogen atom during the final step.
  • Deprotonation
    The removal of a proton from oxygen, resulting in the neutral ether product after reduction.
  • Hg(OAc)2
    A mercury(II) acetate reagent that initiates the formation of the mercury-bridged intermediate in the reaction.
  • Alcohol
    A nucleophile replacing water in alkoxymercuration, leading to ether rather than alcohol as the product.
  • Carbocation Shift
    A rearrangement not observed in this mechanism due to the absence of a true carbocation intermediate.
  • Intermediate
    A transient species, such as the mercury-bridged ion, formed during the multi-step reaction process.
  • Oxygen
    An atom central to ether formation, initially bearing a positive charge before deprotonation in the final product.
  • Product
    The final compound obtained, determined by the nucleophile used—ether if alcohol, alcohol if water.