
John K. answered 07/10/19
Personal Tutor for Organic Chemistry and General Chemistry
It may have to do with the structure and reactivity of the carbocation. Although theoretically planar, the carbocation might be more sterically hindred from the front side; also very reactive carbocations may react so fast that the leaving group is not completely removed from the area, and rear approach by the nucleophile preferably happens. There are several factors to consider: the size and reactivity of the carbocation,, the size and reactivity of the nucleophile, the solvent, the temperature, and concentrations.