enter image description here

Find the total number of possible products

I can think of atleast three reactions that will take place in the acidic medium:

  1. Pinacol-Pinacolone rearrangement
  2. Intermolecular dehydration (leading to ether formation)
  3. Intramolecular dehydration (epoxide formation)

Here are the possible products that would be formed: enter image description here

This gives us a total of $8$ possible products.

Are any different reactions possible? Also, are any of the products that I have listed wrong? (Will any of them not be formed).

  • 1
    $\begingroup$ You have not got any alkenes in there. I think you might get some ethers of allylic alcohols $\endgroup$
    – Waylander
    Jun 3 '20 at 8:42
  • 1
    $\begingroup$ Dihydrobenzofurans may also be possible $\endgroup$
    – Waylander
    Jun 3 '20 at 11:52
  • $\begingroup$ Epoxides are unlikely. Unfortunately your question is too broad. Its author in textbook vastly underestimated practical aspects of such reaction. $\endgroup$
    – Mithoron
    Jun 3 '20 at 14:32
  • $\begingroup$ I agree it's a poorly designed question. But anybody who voted to close as "too broad", could you please explain how "this question currently includes multiple questions in one", the description which you presumably read when voting to close? $\endgroup$
    – orthocresol
    Jun 4 '20 at 12:12