3
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substrate

What will be the major product of this reaction?

I know that this is the OMDM reaction where Alkene is converted to alcohol following the Markovnikov rule. This question is also atypical because all the previous questions used NaBH4 as the demercuration (reducing) agent instead of NaBD4. According to my reasoning, the answer should be:

proposed product

But my answer is incorrect. Please help me out.

PS- Can someone suggest me some website/app where I can draw chemical structures?

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1
  • $\begingroup$ I agree. The the given answer is incorrect. $\endgroup$
    – Waylander
    Commented Nov 14, 2023 at 19:04

1 Answer 1

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Well, the answer is correct except instead of -OH it must be -OMe because the reagent used is Hg(OAc)2/ MeOH and not Hg(OAc)2/H2O.

Here's an illustration of the rection using methanol

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  • $\begingroup$ Ahh! Yes thank you. That is the right answer. $\endgroup$ Commented Nov 15, 2023 at 7:12
  • $\begingroup$ Hey so if we were using D2O instead of MeOH (along with NaBD4) would we get OD instead of OMe? $\endgroup$ Commented Nov 15, 2023 at 7:17
  • 2
    $\begingroup$ Unless there is another proton source in the mix, probably. If there any somewhat acidic protons available, the $\ce{OD}$ would rapidly exchange with them. $\endgroup$
    – TAR86
    Commented Nov 15, 2023 at 11:51

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