Chemistry

Alcohols, Phenols and Ethers

Question:

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

Answer:

In phendl, C – O bond is less polar due to electron withdrawing effect of benzene ring, whereas in methanol C – O bond is more polar due to electron releasing effect of—CH3 group. Hence, the dipole moment of phenol (1.54 D) is smaller than that of methanol (1.71 D).

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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.

Which of the following species can act as the strongest base?
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-12

Q 4.

What happens when benzene diazonium chloride is heated with water?

Q 5.

Classify the following as primary, secondary and tertiary alcohols.
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-1
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Q 6.

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 7.

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

Q 8.

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

Q 9.

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 10.

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

Q 11.

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

Q 12.

Explain why are low molecular mass alcohols soluble in water?

Q 13.

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

Q 14.

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

Q 15.

Which of the following compounds are/is aromatic alcohol?  
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-6

Q 16.

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

Q 17.

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

Q 18.

Show how would you synthesise the following alcohols from appropriate alkanes?
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Q 19.

Write the IUPAC name of the compound given below.
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-25

Q 20.

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

Q 21.

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

Q 22.

Identify aliylic alcohols in the above examples.

Q 23.

Explain why is p-nitrophenol more acidic than phenol?

Q 24.

Write the mechanism of the reaction of HI with methoxymethane.

Q 25.

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

Q 26.

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 27.

Assertion (A): IUPAC name of the compound
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-57
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 28.

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 29.

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

Q 30.

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

Q 31.

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

Q 32.

What is denatured alcohol?

Q 33.

Preparation of alcohols from alkenes involves the electrophilic attack on alkene carbon atom. Explain its mechanism.

Q 34.

Assertion (A): o-Nitrophenol is less soluble in water than the m- and p-isomers.
Reason (R): m-Nitrophenol and p-Nitrophenol exists as associated molecules.

Q 35.

You are given benzene, cone. H2S04and NaOH. Write the equations for the preparation of phenol using these reagents.

Q 36.

Explain the following with an example
(i) Kolbe's reaction (ii) Reimer – Tiemann reaction –
(iii) Williamson ether synthesis (iv) Unsymmetrical ether

Q 37.

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

Q 38.

Write the mechanism of the reaction of HI with methoxybenzene.

Q 39.

Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding phenoxide ions.

Q 40.

(i) Draw the structures of all isomeric alcohols of molecular formula C5HI20 and give their IUPAC names.
(ii) Classify the isomers of alcohols in question (i)as primary, secondary and tertiary alcohols.

Q 41.

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.

Q 42.

Mark the correct increasing order of reactivity of the following compounds with HBr/HCl.
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-15

Q 43.

Write the IUPAC name of the following compounds,
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-23

Q 44.

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

Q 45.

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 46.

Write structures of the products of the following reactions:
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-11

Q 47.

Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.

Q 48.

Explain why is ortho-nitrophenol more acidic than ortho-methoxyphenol?

Q 49.

How are the following conversions carried out?
(i) Propene —> Propan -2-ol
(ii) Benzyl chloride —> Benzyl alcohol
(iii) Ethyl magnesium chloride —> Propan-l-ol
(iv) Methyl magnesium bromide —> 2-Methylpropan-2-ol

Q 50.

Give IUPAC names of the following ethers.
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