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Introduction to Nucleophilic Addition Reactions & Reduction

The triple-bond's sp-hybrid carbon atoms cause to be alkynes more electrophilic than likewise substituted alkenes. As an effect, alkynes sometimes undergo addition reactions that are initiated by bonding to a nucleophile. This mode of reaction, demonstrated below, is normally not shown by alkenes, except the double-bond is activated by electronegative substituents, example- F2C=CF2, or by conjugation with an electron withdrawing group.

HC≡CH   +   KOC2H5 in C2H5OH at 150 ºC   -->   H2C=CH-OC2H5

HC≡CH   +   HCN   +   NaCN (catalytic)   -->   H2C=CH-CN        

The smallest one and most reactive nucleophilic species is possibly an electron. Electron addition to a functional group is from the definition of a reduction, and we noticed earlier that in liquid ammonia to trans-alkenes, alkynes are reduced by solutions of sodium. To identify how this reduction occurs we first need to make out two distinct reactions of sodium with liquid ammonia (boiling point -78 ºC). In the first, sodium dissolves in the pure liquid to give a deep blue solution containing very mobile and loosely bound electrons jointly with solvated sodium cations (first equation shown below). For practical purposes, we can refer such type of solutions to be a source of "free electrons" which might be used as powerful reducing agents. In the case second, with ammonia ferric salts catalyze the reaction of sodium, liberating hydrogen and forming the colorless salt sodium amide (second equation shown below). This is analogous to the reaction of sodium with water to give sodium hydroxide, but because ammonia is 1018 times weaker an acid than water, reaction is less violent. The worth of this reaction is that sodium amide, NaNH2, is an exceedingly strong base (18 powers of ten stronger than sodium hydroxide), which might be employed to convert very weak acids into their conjugate bases.

Na   +   NH3 (liquid, -78 ºC)   -->   Na(+)   +   e(-)   (a blue solution)

Na   +   NH3 (liquid, -78 ºC)   +   Fe   -->   H2   +   NaNH2   (a colorless solution)

Returning to the reducing ability of the blue electron solutions, we can write a probable technique for the reduction of alkynes to trans-alkenes, as displayed below in the diagram. In liquid ammonia the isolated carbon double-bonds are not reduced by sodium, confirming the electronegativity variation between sp and sp2 hybridized carbons.

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