JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o2216
Which reactions involve a skeletal rearrangement (hydride or methyl shift) as the main pathway?
A3,3-dimethylbut-1-ene with HCl
B3-methylbut-1-ene with dilute HX2SOX4
C3,3-dimethylbut-1-ene with BHX3⋅THF then HX2OX2/NaOH
D3,3-dimethylbut-1-ene with Hg(OAc)X2,HX2O then NaBHX4
Answer: A, B
The two ionic additions go through a secondary cation next to a tertiary-forming centre, so shifts occur. Oxymercuration uses a bridged mercurinium ion, and hydroboration is concerted, so neither rearranges.