Question

Complete the curved arrow mechanism of the following double elimination reaction when 2,2-dichloro-3,3-dimethylbutane is treated with two equivalents of sodium amide and heated in mineral oil.

Answer 1

The base abstracts the proton and the simultaneous loss of chloro group resulting in the formation of an alkene and ammonia and chloride ion as by-products. Second mole of the base abstracts another proton by the simultaneous loss of ammonia and chloride ion and resulting in the formation of alkyne as the product The curved arrow mechanism is as follows : NH3 H_N :Cl: CH3 CH3 CH3 CH3 CH3 CH3 Cl: NH3 Cl H_N_H CHj CH3 CH3