1-methyl-1-quarternary ammonium cation(with methyl groups) cyclohexane is heated with hydroxyl ion. I want to find the major product.
In the solution, it is given that a hydrogen attached to the methyl group is eliminated.
1. the methyl group and the cation are not placed in an anti-periplanar configuration, so there would be considerable amount of energy needed (just a guess) to distort the ring;
2. the hydrogen atom attached to the beta carbon on the ring is equally acidic;
3. The transition state for OH eliminating the hydrogen attached to the beta carbon is not crowded. I don't think sterics play a role here.
So I feel like the hydrogen attached to the beta carbon should be eliminated. Why am I wrong?