I was going through the mechanism of Arndt-Eistert synthesis and got stuck in the step where silver ion is used in the rearrangement step. If anyone can clarify the use of silver ion? It would be a great help!

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    $\begingroup$ The silver oxide is used as a catalyst. So it lowers the activation energy of the reaction, but comes out unchanged. $\endgroup$
    – user37142
    Jun 12, 2017 at 6:45
  • $\begingroup$ So why only silver ion? $\endgroup$ Jun 12, 2017 at 6:55
  • $\begingroup$ Or can I use some other ion also? If yes, then can you provide an example! $\endgroup$ Jun 12, 2017 at 6:58
  • $\begingroup$ So, this means that the use of silver ion is determined experimentally. $\endgroup$ Jun 12, 2017 at 7:00
  • $\begingroup$ Yes probably. They tested which catalyst is the most effective. Probably was silver. $\endgroup$
    – user37142
    Jun 12, 2017 at 7:01

1 Answer 1


The step in question here is the so-called Wolff Rearrangement.

In this rearrangement, silver in the form of for example $\ce{Ag2O}$ is used as a catalyst. A catalyst facilitates a reaction (lowering the activation energy), but it comes out of the reaction unchanged (which doesn't mean it's not changed during the reaction, it's just changed back at the end ;))

So why silver? Well, transition metals are good catalysts most of the time for different reasons:

  1. They have vacant d-orbitals which leads to

  2. An easy tendency to exhibit variable oxidation states.

  3. They can form reaction intermediates with reactants.

  4. The presence of defects in their crystal lattices.

(I conveniently copied this list from a quora post, because im lazy)

What this essentially means is that due to their electronic structure, transition metals are often able to bind reactants to their surface and activate them for example. There are quite some catalyst reactions that we don't even understand today, but sometimes it's as easy as this

enter image description here

And why silver? Well probably Wolff just tried a couple of transition metal catalysts and chose the one with the best effect/cost ratio! Theoretical expectations don't always meet reality so often you just have to try and find the right reactants/catalysts.

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    $\begingroup$ can whoever downvoted explain why so I can rectify my mistake? $\endgroup$
    – user37142
    Jun 13, 2017 at 14:28

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