# Why do α-hydroxy ketones give Tollens' test? [duplicate]

I know that tautomerism causes the $\alpha$-hydroxy ketones to give the all the tests of an aldehyde. But how does it exactly tautomerise and what's the intermediate?

Does benzoin gives Tollens' test? If not, why? I'm really confused with this. I read somewhere that benzoin doesn't give Tollens' test as it does not have an alpha carbon to form enediol intermediate. Please help.

The misconception that you have is that all alpha-hydroxy ketones can give a positive Tollens' test. Aldehydes give a positive test, and so only alpha-hydroxy ketones that can tautomerize to aldehydes will give a positive Tollen's test. My example above is 1-hydroxy-2-propanone, which isomerizes to 2-hydroxypropanol. Most alpha-hydroxy ketones with names that match the pattern 1-hydroxy-2-alkanone will give a positive Tollens' test.
• Can you put the answer to your final question in spoiler blockquotes (>)? Or maybe just state it here? Is the answer to "What does benzoin form upon tautomerization?" simply benzoin itself. – Gaurang Tandon Mar 15 '18 at 15:27