Identify whether the given compound will get oxidised by Tollen's reagent.
![7‐oxabicyclo[2.2.1]heptan‐1‐ol](https://i.sstatic.net/Co5WF.png)
The problem here is with the bridged alpha carbon. It cannot pertain sp2 character in the middle of the reaction as it is not permittable according to Bredt's rule.
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2$\begingroup$ Is the answer given, yes? I too think you are right, and also, tollen's reagent oxidises only compounds with free CHO group, like aldehydes and alpha hydroxy ketones, so why should this give positive tollen's test? $\endgroup$– V.GCommented May 20, 2021 at 15:46
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$\begingroup$ I agree. I think this will not get oxidised by Tollens $\endgroup$– WaylanderCommented May 20, 2021 at 15:55
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1$\begingroup$ The structure shown is 7-oxabicyclo[2.2.1]heptan-4-ol, which exists as 4-hydroxycyclohexanone, and not the title compound, 7-oxabicyclo[2.2.1]heptan-3-ol. Neither compound will be oxidized by Tollen's reagent (cc. @Waylander). $\endgroup$– user55119Commented May 20, 2021 at 16:53
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$\begingroup$ The answer given was incorrect and even I thought so. Now it's cleared $\endgroup$– Abhishek PCommented May 20, 2021 at 17:42
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1$\begingroup$ @AbhishekP If you got your answer, feel free to self-answer it. Self-answering is always encourages and it will help future readers. $\endgroup$– Nilay GhoshCommented May 21, 2021 at 2:25
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