Question

7.11 CARBOCATION STABILITY PRACTICE PROBLEM 7.18 compound called isoborneol is heated with 9 M sulfuric acid, the product of ction is the compound called camphene and not bornylene, as one might expect. with 9 M sulfuric acid, the product of Using models to models to assist you, write a step-by-step mechanism showing how camphene is formed. When the compound call the reaction is the com HO Hot a not not heat Bornylene Isoborneol Camphene 7.11B Rearrangement After Dehydration of a Primary Alcohol Rearrangements also accompany the dehydration of primary alcohols. Since a primary car- bocation is unlikely to be formed during dehydration of a primary alcohol, the alkene that is produced initially from a primary alcohol arises by an E2 mechanism. us described in Section 7.10C. However, an alkene can accept a proton to generate a car n in a process that is essentially the reverse of the deprotonation step in the El dehydration of an alcohol (Section 7.10A). When a terminal alkene electrons to bond a proton at the terminal carbon, a carbocar of the chain." ormation of a Rearranged Alkene Du hydration of a Primary Alcohol JA MECHANISM

I just can get this question. plz explain step by step

Answer 1

Above question is an example of Wagner-Meerwein rearrangement. This rearrangement involves migration of hydrogen, alkyl group, aryl group or even bond which is anti to the leaving group. The detail mechanism is shown below-

Que. Given reaction is an example of Wagner - Meerwein rearrangement which involves migration of hydrogen, alkyl or aryl group from one carbon to adjacent carbon. Isoborneo) Isoborneol ☆ Migration of Migration of the anti-bond 2 carbocation 2- carbocation [less stable] [More stable] Conversion of less stable carbocation to more stable carbocation is the driving force for this rearrangement. [camphene