This question came in one of my school tests. They had given us an unsymmetrical pinacol i.e 1,1-diphenyl-2-methylpropane-1,2-diol and asked us whether it will give only one pinacolone or not.According to me, I had assumed that carbocation will be formed on the diphenyl-substituted carbon due to which a methyl shift will occur and we will get only one product. But my teacher marked it wrong and said that more than one pinacolone is possible here. Could anyone please explain HOW ??

This question came in one of my school tests. They had given us an unsymmetrical pinacol i.e 1,1-diphenyl-2-methylpropane-1,2-diol and asked us whether it will give only one pinacolone or not.

According to me, I had assumed that carbocation will be formed on the diphenyl-substituted carbon due to which a methyl shift will occur and we will get only one product. But my teacher marked it wrong and said that more than one pinacolone is possible here.

How is it possible?

This question came in one of my school tests. They had given us an unsymmetrical pinacol i.e 1,1-diphenyl-2-methylpropane-1,2-diol and asked us whether it will give only one pinacolone or not.According to me, I had assumed that carbocation will be formed on the diphenyl-substituted carbon due to which a methyl shift will occur and we will get only one product. But my teacher marked it wrong and said that MORE THAN ONE PINACOLONE is possible here. Could anyone please explain HOW ??

This question came in one of my school tests. They had given us an unsymmetrical pinacol i.e 1,1-diphenyl-2-methylpropane-1,2-diol and asked us whether it will give only one pinacolone or not.According to me, I had assumed that carbocation will be formed on the diphenyl-substituted carbon due to which a methyl shift will occur and we will get only one product. But my teacher marked it wrong and said that more than one pinacolone is possible here. Could anyone please explain HOW ??