Carbocations are very unstable, so it be wrong to assume that a hydride shift from a primary carbocation to a tertiary one wouldn\'t be possible due to their stability. Would it be possible for there to occur a hydride shift across two secondary carbocations towards a tertiary carbocation because secondary carbocations are more stable? Also, how many, consecutive times, can a hydride shift occur and under what circumstances? Solution Tertiary carbocation is the most stable. It is more stable as compared to primary carbocation. Hence hydride shift would possibly occur in primary carbocation to form tertiary carbocation. Also, secondary carbocation are less stables as compared to tertiary carbocation. Hence hydride shift will occur across to secondary carbocations to form tertiary carbocation. Hydride shift occurs twice in a primary carbocation to form tertiary carbocation, it occurs once in a primary carbocation to form secondary carbocation and once in secondary carbocation to form tertiary carbocation. .