Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
The relative yield of the following alkenes produced by the reaction of trans -1-chloro-2-methylcyclohexane with KOH and heat is: (i) 1-Methylcyclohexene (ii) Methylenecyclohexane (iii) 3-Methylcyclohexene
Options
- A(i) > (iii) > (ii)
- B(iii) > (i) > (ii)
- C(ii) > (iii) > (i)
- D(i) > (ii) > (iii)
Correct answer
B. (iii) > (i) > (ii)
Step-by-step solution
The reaction of an alkyl halide with KOH and heat proceeds via the E2 elimination mechanism. E2 elimination in cyclohexanes requires an anti-periplanar geometry between the leaving group (Cl) and the -hydrogen. This means both must occupy axial positions in the chair conformation. In trans -1-chloro-2-methylcyclohexane, the molecule exists in an equilibrium between the diequatorial (e,e) and diaxial (a,a) conformations. For E2 elimination to occur, the ring must adopt the conformation where the Cl atom is axial. In