Does 3-hydroxy-penta-2-one give positive Tollen's test?

Asked May 05 '22 at 02:42

Active May 05 '22 at 09:38

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I know that alpha hydroxy ketones that can tautomerise to an aldehyde give positive Tollen's test because an aldehyde gives a positive Tollen's test. This molecule however doesn't tautomerise (or double tautomerise) to an aldehyde, yet it gives a positive test why?

EDIT: the question linked in comments shows the mechanism of the reduction of Tollens reagent only for an $\alpha$-hydroxy ketone that has the hydroxy group on the terminal carbon.

edited May 05 '22 at 09:38

asked May 05 '22 at 02:42

Dev patel

Alpha hydroxy ketones always give a positive Tollen's Test. Refer this: Why do α-hydroxy ketones give Tollens' test? – Nisarg Bhavsar May 05 '22 at 05:06
2

@NisargBhavsar Yes they do, I just want a mechanism in which the hydroxy group is not on the terminal carbon but somewhere in between, because if the hydroxy group is on the terminal carbon it easily forms an aldehyde. However, this is not the case with the compound above. – Dev patel May 05 '22 at 09:37
https://youtu.be/xlaKvKfNidA this answers everything – Ritil Jul 30 '22 at 19:00

Does 3-hydroxy-penta-2-one give positive Tollen's test?

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