Reaction of Alkynes

Basic Chemistry_Derio Gusvandi_RSA1C111014

With the fog of electrons (bonding ) surrounding the bond, alkyne compound is a nucleophile, which will react with an electrophile. Alkyne has two bonds, so it can mengadisi to 2 molecules, depending on the reagents and conditions.

Alkyne compound is less reactive than alkene compounds.

The relative stability of several carbocations:

1. Addition of Hydrogen Halides Addition of hydrogen halides (HX) on the last alkyne compounds similar to those seen in the alkene compounds. If the triple bond is at the end of the alkyne compound (terminal alkyne), the H+ will be bound to the sp carbon atoms that have bonded with hydrogen, producing secondary vinyl cation (according to the Markovnikov rule).

REACTION MECHANISM Suppose for the reaction between HCl with alkyne compound: bond is relatively weak will split because the electrons in the bond was withdrawn by the protons on the electrophile compounds.

Intermediate in the form of positively charged carbocation will quickly react with the negatively charged chloride ions.

 If the addition of HX occurs in an internal alkyne, it will form two kinds of geminal dihalides, the first proton adducts can occur at C-2 or C-3 (carbon sp) with the same ease.

2.

Water Addition With the acid, alkyne compounds undergo addition reactions in water.

In the case of water addition reactions, terminal alkyne is less reactive than the internal alkyne. Terminal alkyne would mengadisi water if Hg2 + ion is added to the reaction mixture acidic.

3.

Hydrogen Addition A. Catalytic hydrogenation of alkanes With the presence of metal catalysts such as Pt, Pd or Ni, alkyne compound may be a compound of hydrogen alkanes additioned.

Catalytic hydrogenation takes 2 stages with intermediate form alkene compounds. With an efficient catalyst such as Pt, Pd, or Ni, the reaction may be terminated only on the product alkene.

B. CIS-catalytic hydrogenation of alkenes Alkyne hydrogenation of alkenes can be stopped at this stage by using a catalyst partially deactivated. Lindlar catalyst is a catalyst made of Pd and poisoned with quinoline. Nickel boride (Ni2B is the latest alternative to Lindlar catalyst that made it easier and gives better results.

4. Halogen Adducts Bromine and chlorine could mengadisi the alkyne as occurs in alkenes. Jika1 mol mol alkyne pada1 mengadisi halogen, it will produce dihaloalkena.

5. Halogen Halide Adducts Hydrogen halide (HX) can mengadisi the three compounds alkyne bond as occurs in addition to the two compounds alkene double bond, with the initial product is the vinyl halide. If HX adduct the alkyne end, it will produce products with Markovnikov orientation following the rules. Second adduct of HX molecule orientation as the first.

MECHANISM

If 2 mol mol HX adduct to 1 alkyne, then the second mole adduct usually the same orientation with the first addition.