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  Irreversible Addition Reactions Homework Help - K-12 Grade Level, College Level Chemistry

Introduction to Irreversible Addition Reactions

The variation between reversible and irreversible carbonyl addition reactions might be explained clearly by considering the stability of alcohols that having the structure displayed below in the shaded box of the diagram.

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If substituent Y is not a hydrogen, an aryl group or an alkyl group, there is a good possibility the compound will be unstable (not isolable), and will decompose in the way displayed. Many hydrates and hemiacetals (Y = OH & OR), for instance, are known to decompose spontaneously to the subsequent carbonyl compounds. Aminols (Y = NHR) are intermediates in imine formation and also revert to their carbonyl precursors if dehydration conditions are not used. Similarly, α-haloalcohols (Y = Cl, Br & I) cannot be isolated, because they instantaneously decompose with the loss of HY. In all these examples addition of H-Y to carbonyl groups is visibly reversible.
An alkyl group or an aryl group, the resulting alcohol is the stable compound and does not decompose with loss of hydrocarbons or hydrogen, yet on heating, if substituent Y is a hydrogen. It follows then, that if nucleophilic reagents subsequent to H:(-), R:(-) or Ar:(-) add to aldehydes and ketones, the alcohol results of such type of additions will form irreversibly. Free anions of this type would be very strong bases and nucleophiles, but their unexpected reactivity would make them hard to prepare and use. Providentially, metal derivatives of these alkyl, hydride and aryl and moieties are presented and allow their addition to carbonyl compounds.

  • Aldehydesandketones alsogo through addition reactions that are essentially irreversible.
  • These reactions make use of organometallicreagentsto add alkylgroups to thecarbonyl carbon atom.
  • Thosereactionsare nucleophilic additions; this meansthatthe organic groupadded is acting like a nucleophile in thereaction

We're accustomed to electrophilic nature of alkyl groups (that is carbocations), but how does an alkyl group act as a nucleophile, is shown in the diagram.

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