Q. 135.0( 2 Votes )

Explain the follo

Answer :

(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses due to the following reasons:


In alcohols, hydroxyl group (OH) is present which helps in the formation of hydrogen bonds between alcohol and water molecules.



Hence, alcohols are soluble in water.


On the other hand, in hydrocarbon there is no hydroxyl group is present and as a result hydrogen bonding is absent. Hence, hydrocarbon is less soluble in water than alcohol.


(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.


More easily the removal of proton takes place, higher will be its acidic strength


Electron-donating groups such as –CH3, -OCH3, -NH2, etc. decrease the acidity.


Electron-withdrawing groups such as –NO2, -CN, -SO3H, -COOH, -X(halogen), etc. increase the acidity of phenol.


Electron-withdrawing groups stabilizes the phenoxide ion by dispersing (decreases) the negative charge relative to phenol increase the acidic strength of phenols.


Electron-donating groups destabilizes the phenoxide ion by intensifying (increasing) the negative charge relative to phenol tend to decrease the acidic strength of phenols.



In ortho-methoxyphenol, CH3 group is present and as we know that CH3 group is an electron donating(releasing) group which decreases the acidic strength of phenol.


In ortho-nitrophenol, NO2 group is present. As we know that NO2 group is an electron withdrawing group which increases the acidic strength of phenol.


Thus, orhto-nitrophenol is more acidic than ortho-methoxyphenol.


(iii) Cumene is a better starting material for the preparation of phenol.


The reaction for the preparation of phenol from cumene is given below:



As we can see that cumene undergoes hydrolysis with an aqueous acid to from phenol and also a side product acetone which is itself an another important organic compound.


Thus, Cumene is a better starting material for the preparation of phenol.


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