[ashish]

this is the screenshot of the problem ...problem (i)

https://postimg.org/image/t44cepx6j/

please ignore that five bond in the product ,

its tertiary alcohol to ketone and the bottom one is getting transformed into lactone

i think because of ring we cant use NaIO4...so what reagent to use in this ??

any suggestion please ??

[kriggy]

Well we cant ignore that because 5 bonded carbons dont exist. There must be a mistake in the problem or it is a tricky question to see if you realize that

[ashish]

Well we cant ignore that because 5 bonded carbons dont exist. There must be a mistake in the problem or it is a tricky question to see if you realize that

thats a mistake or misprint  in the question...please tell me whether periodate oxidation will work or not ??

[Babcock_Hall]

Well we cant ignore that because 5 bonded carbons dont exist. There must be a mistake in the problem or it is a tricky question to see if you realize that

5-bonded carbons do in Texas:  http://chemistry.about.com/od/T-Organic-Terms/fl/Texas-Carbon-Definition.htm

[rolnor]

It should work with periodate but the bond between the ketogroups should be cleaved in the product?

[Dan]

I think because of ring we cant use NaIO4...so what reagent to use in this ??

Why do you think periodate will not react with cyclic diols?

[ashish]

I think because of ring we cant use NaIO4...so what reagent to use in this ??

Why do you think periodate will not react with cyclic diols?

i thought maybe because of the ring the two OH will not come together to react with periodate...but i guess it will work thank-you all