Acidic dehydrogenation of alcohol

Will there be a hydride shift to form a tertiary carbocation or will it proceed as secondary carbocation?

My text book shows that it would proceed as secondary carbocation But tertiary carbocation is more stable. I am a bit confused here. Will someone please clarify?

  • 1
    $\begingroup$ Depends on the reaction conditions... $\endgroup$
    – Zhe
    Nov 14, 2017 at 22:08
  • $\begingroup$ Please cite the textbook. $\endgroup$
    – NotEvans.
    Nov 14, 2017 at 22:54
  • $\begingroup$ Can you please elaborate what kind of conditions? @Zhe $\endgroup$
    – Soura
    Nov 15, 2017 at 20:13
  • $\begingroup$ Temperature, solvent, etc. $\endgroup$
    – Zhe
    Nov 16, 2017 at 2:03

1 Answer 1


It will surely proceed as a secondary carbocation and no hydride shift will take place. Because if hydride shift takes place, bridgehead carbon will acquire positive charge i.e. will become unstable.

For detailed explanation check this out: Why are bridge bonds with negative or positive charge on bridge head unstable?


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