Show with the help of chemical equations what happens when cumene hydroperoxide is treated with dilute H2SO4.

When cumene hydroperoxide is treated with dilute sulphuric acid, it gives phenol and acetone.

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Account for the following:
tert-butanol is more volatile than n-butanol.


tert-butanol and n-butanol have the same molecular mass but t-butanol is more branched. As branching increases, Van der Waals forces increases due to decrease in surface area, t-butanol has a lower boiling point than n-butanol. Hence t-butanol is more volatile than n-butanol.
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Give a chemical test to distinguish between: 2-pentanol and 3-pentanol.


2-pentanol on oxidation gives methylketone.


This compound has a CH3C = O group.
Therefore, it will form iodoform (CHI3) with iodine and alkali on warming. Iodoform is a yellow crystalline substance.



3-pentanol does not show this test.

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Write the resonance structures of phenol (which is similar to that of chlorobenzene) and explain why it does not form chlorobenzene on reaction with PCI5 Explain whether phenol can be dehydrated on heating with catalytic amounts of conc. H2SO4.


Resonance structures of phenol:



Due to resonance, carbon-oxygen bond develops a slight double bond character. Therefore, it is not easy to replace —OH in phenols by Cl.
No, phenols cannot be dehydrated on heating with small amount of conc. H2SO4. Instead, phenols with conc. H2SO4 undergoes sulphonation.

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Account for the following:
Alcohols with three or less carbons are water-soluble while alcohols with five or more carbons are insoluble.


The solubility of alcohols in water is due to the presence of intermolecular hydrogen bonding. As the molecular mass increases, the solubility in water decreases. Greater carbon content makes the alcohols less water solubility.
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