Does Anti-Markovnikov behaviour extend only to additions to alkenes?

1 Answer
Jun 12, 2015

Anti-Markovnikov behaviour extends to other chemical reactions than additions to alkenes, but they are relatively rare.

Explanation:

For example, the hydration of phenylacetylene gives acetophenone in a Markovnikov addition.

"PhC≡CH" +"H"_2"O" → "PhCOCH"_3

But hydration in the presence of a complex ruthenium catalyst gives phenylacetaldehyde in an anti-Markovnikov addition.

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A few other anti-Markovnikov reactions involving transition metal catalysts are also known.