Give two reactions that show the acidic nature of phenol. Compare its acidity with that of ethanol.
The reactions showing acidic nature of phenol are:
(a) Reaction with sodium: Phenol reacts with active metals like sodium to liberate H, gas.
(b) Reaction with NaOH: Phenol dissolves in NaOH to form sodium phenoxide and water.
Phenol is more acidic than ethanol. This is due to the reason that phenoxide ion left after the loss of a proton from phenol is stabilized by resonance, while ethoxide ion left after less of a proton from ethanol, is not.
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.
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): Phenol forms 2,4, 6-tribromophenol on treatment with Br2 in carbon disulphide at 273 K.
Reason (R): Bromine polarizes in carbon disulphide.
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]
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?
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?
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.
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
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.
Write the equation of the reaction of hydrogen iodide with (i)1-propoxypropane (ii)methoxybenzene, and (iii)benzyl ethyl ether
Explain why is OH group in phenols more strongly held as compared to OH group in alcohols.
Explain how does the – OH group attached to a carbon of benzene ring activate it towards electrophilic substitution?
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.
Mark the correct increasing order of reactivity of the following compounds with HBr/HCl.
Why is the reactivity of all three classes of alcohols with cone. HCl and ZnCl2 (Lucas reagent) different?
Show how are the following alcohols prepared by the reaction of a suitable Grignard reagent on methanal ?
You are given benzene, cone. H2S04and NaOH. Write the equations for the preparation of phenol using these reagents.
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
When 3-methylbutant 2-ol is treated with HBr, the following reaction takes place:
Give a mechanism for this reaction.
(Hint: The secondary carbocation formed in step II rearranges to a more stable tertiary carbocation by a hydride ion shift from 3rd carbon atom.)
Which of the following are used to convert RCHO into RCH2OH?
(a) H2/Pd
(b) LiAlH4
(c) NaBH4
(d) Reaction with RMgX followed by hydrolysis
Which of the following reagents can be used to oxidize primary alcohols to aldehydes?
(a) CrO3 in anhydrous medium
(b) KMnO4 in acidic medium
(c) Pyridinium chlorochromate
(d) Heat in the presence of Cu at 573 K
When phenol is treated with bromine water, white precipitate is obtained. Give the structure and the name of the compound formed.
