further chem

  • useful for addition to carbonyl carbons
  • good for lengthening carbon chains

alkynes are acidic enough (sp) that they can be deprotonated by nitrogen bases () and form sodium acetylides that react similarly as other organometallics

reacts with to get carboxylic acids
reacts with for primary alcohols

reduces carbonyl compounds

18-electron rule to determine stability

  • unstable complexes break down

  • no more than 18 electrons for a stable complex

  • organolithiums in non-polar is okay

  • when using organometallics to make other organometallic reagents, substituent group needs to be more basic

reactions of organometallics

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