Arrange water, ethanol and, phenol in increasing order of acidity and give reason for your answer.
Increasing order of acidity is: ethanol < water < phenol.
This is because the phenoxide ion obtained after the removal of H+ is resonance stabilised, while the ethoxide ion obtained after the removal of H+ is destabilised by +1 effect of ethyl group. Thus phenol is a stronger acid than ethanol.
Now, ethanol is a weaker acid than water because the electron releasing ethyl group increases the ethanol density on oxygen and consequently the proton will not be released easily. There is no such effect is water.
Write structures of the compounds whose IUPAC names are as follows:
(i)2-Methylbutan-2-ol
(ii)l-Phcnylpropan-2-ol
(iii)3,5-DimethyIhexane-l,3,5-triol
(iv)2,3-Dicthylphenol
(v)1-Ethoxypropane
(vi)2-Ethoxy-3-methylpentane
(vii) Cyclohexylmethanol
(viii) 3-Cyclohexylpcntan-3-ol
(ix)Cyclopcnt-3-en-l-ol
(x)4-ChIoro-3-ethylbutan-l-ol
Assertion (A): Phenols give o-nitrophenol and p-nitrophenol on nitration with cone. HNO3 and H2SO4 mixture.
Reason (R): -OH group in phenol is o-,p-directing.
Assertion (A): Phenol forms 2,4, 6-tribromophenol on treatment with Br2 in carbon disulphide at 273 K.
Reason (R): Bromine polarizes in carbon disulphide.
Ethers can be prepared by Williamson's synthesis in which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether cannot be prepared by this method. Explain.
Assertion (A): IUPAC name of the compound
Reason (R): In IUPAC nomenclature, ether is regarded as hydrocarbon derivative in which a hydrogen atom is replaced by -OR or -OAr group [where R = alkyl group and Ar = aryl group]
Write the equation of the reaction of hydrogen iodide with (i)1-propoxypropane (ii)methoxybenzene, and (iii)benzyl ethyl ether
Why is the C – O – H bond angle‘in alcohols slightly less than the tetrahedral angle whereas the C – O – C bond angle in ether is slightly greater?
Give structures of the products you would expect when each of the following alcohol reacts with (a)HCl-ZnCl2 (b)HBrand (c) SOCl2
(i)Butan-1-ol
(ii)2-Methylbutan-2-ol
Nitration is an example of aromatic electrophilic substitution and its rate depends upon the group already present in the benzene ring. Out of benzene and phenol, which one is more easily nitrated and why?
Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.
While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile. Give reason.
Explain how does the – OH group attached to a carbon of benzene ring activate it towards electrophilic substitution?
Write the names of reagents and equations for the preparation of the following ethers by Williamson's synthesis:
(i)1-Propoxypropane
(ii)Ethoxybenzene
(iii)2-Methoxy-2-methylpropane
(iv)1-Methoxyethane
Mark the correct increasing order of reactivity of the following compounds with HBr/HCl.
Explain why is OH group in phenols more strongly held as compared to OH group in alcohols.
Show how are the following alcohols prepared by the reaction of a suitable Grignard reagent on methanal ?
Give equations of the following reactions:
(i)Oxidation of propan-l-ol with alkaline KMnO4 solution.
(ii)Bromine in CS2 with phenol.
(iii)Dilute HNO3 acid with phehoL
(iv)Treating phenol with chloroform in presence of aqueous NaOH.
Explain the fact that in aryl alkyl ethers (i) the alkoxy group activates the benzene ring towards electrophilic substitution and (ii) it directs the incoming substituents to ortho and para positions in benzene ring.
When phenol is treated with bromine water, white precipitate is obtained. Give the structure and the name of the compound formed.
Arrange the following compounds in increasing order of acidity and give a suitable explanation:
Phenol, o-Nitrophenol, o-Cresol
Why is the reactivity of all three classes of alcohols with cone. HCl and ZnCl2 (Lucas reagent) different?
Explain why alcohols and ethers of comparable molecular mass have different boiling points.
Assertion (A): Boiling points of alcohols and ethers are high.
Reason (R): They can form intermolecular hydrogen bonding.
You are given benzene, cone. H2S04and NaOH. Write the equations for the preparation of phenol using these reagents.
Give two reactions that show the acidic nature of phenol. Compare its acidity with that of ethanol.
