Integrated SequencePhysics Chemistry Organic Biology

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The Chemical Bond

Chemical Thermodynamics and the Equilibrium State

Acids and Bases

Organic Acids and Bases

Nucleophiles and Electrophiles

Reactions of Alkynes

The triple bond of an alkyne is comprised of an sp-sp σ bond and two p-p π bonds. As with alkenes, the π electrons of alkynes are subject to attack by Lewis acids (electrophiles), and so alkynes can undergo electrophilic addition reactions. Additionally, though, unlike alkanes and alkenes, terminal alkynes and acetylene possess significant (though still very weak) acidity. This is due to the fact that upon ionization, the unshared electron pair of the anion is bound within an sp hybrid orbital, which, having more s character than sp2 or sp3 orbitals, binds the electron pair at lower energy than those types. The capacity of terminal alkynes to form their anion conjugate bases is an important tool in organic synthesis for forming new carbon-carbon bonds because these anions can be employed as nucleophiles.

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