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Alkyne Nomenclature

Alkyne Nomenclature. Common names (derivatives of acetylene). Alkyne Nomenclature. Replace “-ane” with “-yne” Terminal alkynes 1-butyne Internal alkynes 2-pentyne. Alkyne Nomenclature. Replace “-ane” with “-yne” Terminal alkynes 1-butyne Internal alkynes 2-pentyne

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Alkyne Nomenclature

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  1. Alkyne Nomenclature • Common names (derivatives of acetylene)

  2. Alkyne Nomenclature • Replace “-ane” with “-yne” • Terminal alkynes 1-butyne • Internal alkynes 2-pentyne

  3. Alkyne Nomenclature • Replace “-ane” with “-yne” • Terminal alkynes 1-butyne • Internal alkynes 2-pentyne • Alkyne is given lowest number

  4. Alkyne Nomenclature • When more than one triple bond use diene, triene....... • If a double and a triple bond are present, number to give the lowest # • If multiple functional groups are present, use both suffixes.

  5. Alkyne Nomenclature • Practice:

  6. Alkyne Nomenclature • Propargyl group is used in common names (similar to the allyl group)

  7. Physical Properties • All hydrocarbons have similar properties • Alkynes similar to alkenes and alkanes • Less dense than water • Low polarity • Bp increase with MW • Alkynes are more linear than alkenes • Triple bond is more polarizable than C=C • Stronger van der Waals interactions

  8. Structure of Alkynes • sp hybridized carbons • Bond angle is 180o

  9. Structure of Alkynes • sp hybridized carbons • Overlap of p orbitals to form p bonds

  10. Reaction Considerations • Alkynes are e- rich (they are nucleopliles) • Alkynes undergo electrophilic addition Rx • Regioselective addition (Markovnikov’s Rule) • The resulting alkene can also react

  11. Priorities and Stability

  12. Alkyne Reactions • Hydrogen Halide addition • Addition of Water • Mercuric-ion-catalyzed hydration • Hydroboration – oxydation • Hydrogenation • Pd or Pt • Lindlars • Na or Li • Acetylice ion

  13. Acidity of H on an sp C • The H attached to an sp hybridized C is acidic • This explains some reactions of alkynes Alkynes

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