Chemistry

Alcohols, Phenols and Ethers

Question:

Arrange water, ethanol and, phenol in increasing order of acidity and give reason for your answer.

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.
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Alcohols, Phenols and Ethers

Q 1.

The carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why?

Q 2.

Assertion (A): Boiling points of alcohols and ethers are high.
Reason (R): They can form intermolecular hydrogen bonding.

Q 3.

What happens when benzene diazonium chloride is heated with water?

Q 4.

Name the enzymes and write the reactions involved in the preparation of ethanol from sucrose by fermentation.

Q 5.

Arrange the following compounds in decreasing order of acidity:
H2O, R-OH, HC = CH

Q 6.

Explain why is OH group in phenols more strongly held as compared to OH group in alcohols.

Q 7.

Assertion (A): Bond angle in ethers is slightly less than the tetrahedral angle. Reason (R): There is a repulsion between the two bulky (-R) groups.

Q 8.

Explain a process in which a biocatalyst is used in industrial preparation of a compound known to you.

Q 9.

Explain why are low molecular mass alcohols soluble in water?

Q 10.

Classify the following as primary, secondary and tertiary alcohols.
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Q 11.

Which of the following species can act as the strongest base?
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Q 12.

Explain why alcohols and ethers of comparable molecular mass have different boiling points.

Q 13.

Assertion (A): Ethanol is a weaker acid than phenol.
Reason (R): Sodium ethoxide may be prepared by the reaction of ethanol with aqueous NaOH.

Q 14.

Give reason for the higher boiling point of ethanol in comparison to methoxymethane.

Q 15.

Show how would you synthesise the following alcohols from appropriate alkanes?
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Q 16.

Which of the following compounds are/is aromatic alcohol?  
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Q 17.

Why is the reactivity of all three classes of alcohols with cone. HCl and ZnCl2 (Lucas reagent) different?

Q 18.

When phenol is treated with bromine water, white precipitate is obtained. Give the structure and the name of the compound formed.

Q 19.

Name the factors responsible for the solubility of alcohols in water.

Q 20.

Explain why is O = C = O nonpolar while R – O – R is polar.

Q 21.

Identify aliylic alcohols in the above examples.

Q 22.

Write the IUPAC name of the compound given below.
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Q 23.

Explain why is p-nitrophenol more acidic than phenol?

Q 24.

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

Q 25.

Write the mechanism of the reaction of HI with methoxymethane.

Q 26.

Phenol can be distinguished from ethanol by the reactions with ………….
(a) Br2/water (b) Na
(c) Neutral FeCl3 (d) All of these

Q 27.

Suggest a reagent for conversion of ethanol to ethanal.

Q 28.

While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile. Give reason.

Q 29.

Write the structures of the isomers of alcohols with molecular formula C4H10O. Which one of these isomers exhibits optical activity?

Q 30.

Mark the correct increasing order of reactivity of the following compounds with HBr/HCl.
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Q 31.

Assertion (A): p-Nitrophcnol is more acidic than phenol.
Reason (R): Nitro group helps in the stabilization of the phenoxide ion by dispersal of negative charge due to resonance.

Q 32.

Assertion (A): IUPAC name of the compound
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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]

Q 33.

Write the mechanism of the reaction of HI with methoxybenzene.

Q 34.

Give two reactions that show the acidic nature of phenol. Compare its acidity with that of ethanol.

Q 35.

Explain how does the – OH group attached to a carbon of benzene ring activate it towards electrophilic substitution?

Q 36.

Out of 2-chloroethanol and ethanol which is more acidic and why?

Q 37.

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?

Q 38.

Match the starting materials given in Column I with the products formed by these (Column II) in the reaction with HI.
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Q 39.

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

Q 40.

What is denatured alcohol?

Q 41.

Out of o-nitrophenol and o-cresol which is more acidic?

Q 42.

In Kolbe's reaction, instead of phenol, phenoxide ion is treated with carbon dioxide. Why?

Q 43.

Dipole moment of phenol is smaller than that of methanol. Why?

Q 44.

Arrange water, ethanol and, phenol in increasing order of acidity and give reason for your answer.

Q 45.

Which of the following is an appropriate set of reactants for the preparation of l-methoxy-4- nitrobenzene and why?
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Q 46.

What is the correct order of reactivity of alcohols in the following reaction?
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Q 47.

Write the IUPAC name of the following compounds,
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Q 48.

Suggest a reagent for the following conversion.
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Q 49.

Out of o-nitrophenol and p-nitrophenol, which is more volatile? Explain.

Q 50.

Explain why nucleophilic substitution reactions are not very common in phenols.