[orgoclear]

Based on the options. it indicates that the substrate undergoes CR (Cannizarro) and then intramolecular esterification.

I am worried about which of the carbonyl groups acts as hydride donor, the CHO or CDO.

I am inclined to think that since the CDO carbon is more electrophilic, it will undergo CR faster.. but then rate determining step is hydride transfer for which CHO is more reactive.

But if the carbonyl carbon is not sufficiently electrophilic, i dont think that the initial nucleophilic addition would be quite viable..

So which carbonyl group will be the hydride donor?

[fawad0418]

probably u shd get (b) as the answer...

[orgoclear]

why?

[orgoclear]

why ? (again)

[sjb]

Does the electronics implied by the methoxy and nitro groups help at all?

[orgoclear]

Does the electronics implied by the methoxy and nitro groups help at all?

I know that the OMe group deactivates the CHO group towards nucleophilic addition and increases its hydride donating capabilities

The NO2 group activates the CDO group towards nucleophilic addition and decreases its hydride donating capabilities


So how do I weigh them together?

[srihari]

I think the answer is A
the reaction proceed as follows , the CDO carbon being more electrphilic is more prone to OH- attack
and hence OH- attacks there , then the resulting intermediate has a loss of proton the one on OH .. so
there is quite a good build up of negative charge and hence the D- leaves and attacks the other CHO carbon .
and then usual steps ..follow

regards
Srihari