IIT JEE , AIEEE Forum - Chemistry , Organic Chemistry

(2)

There exist the automeric forms

CH3-CO-CH2-COOC2H5 in equilibrium with CH3-C(OH)doublebondC-COOC2H5

whch are correct

a)%of form 1 incs in H2O

b)%of form 1 decs in H2O

c))%of form 2 incs in ether

d)%of form 1 incs on increasing temp

multiple answer

please explain soon

madhusudan.chavan

6388

Any solvent that can form hydrogen bonds with the carbonyl group of the keto form will cause a decrease in entropy. However, the enol form, Since it forms an intramolecular hydrogen bond, will largely be prevented from forming hydrogen bond with the solvent, and consequently there will be smaller decrease in entropy. Thus solvents such as water, methanol, acetic acid,etc. tend to reduce the enol content. On the other hand, solvents such as hexane, benzene, etc. the enol content will be larger.

Thus % of enol form will be more in ether.

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