Chemistry

Alcohols, Phenols and Ethers

Question:

Explain why are low molecular mass alcohols soluble in water?

Answer:

The lower members of alcohols are highly soluble in water but the solubility decreases with increase in molecular weight. The solubility of lower alcohols in water is due to the formation of hydrogen bonds between alcohols and water molecules.
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Alcohols, Phenols and Ethers

Q 1.

Classify the following as primary, secondary and tertiary alcohols.
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Q 2.

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.

Q 3.

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 4.

Which of the following species can act as the strongest base?
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Q 5.

Suggest a reagent for conversion of ethanol to ethanal.

Q 6.

How can propan-2-one be converted into tert-butyl alcohol?

Q 7.

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

Q 8.

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

Q 9.

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

Q 10.

Explain why propanol has higher boiling point than that of the hydrocarbon, butane?

Q 11.

Give IUPAC names of the following ethers.
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Q 12.

Which of the following compounds are/is aromatic alcohol?  
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Q 13.

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

Q 14.

What is denatured alcohol?

Q 15.

What happens when benzene diazonium chloride is heated with water?

Q 16.

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

Q 17.

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

Q 18.

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 19.

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

Q 20.

Write the mechanism of hydration of ethene to yield ethanol.

Q 21.

Name the reagents used in the following reactions:
(i)Oxidation of a primary alcohol to carboxylic acid.
(ii)Oxidation of a primary alcohol to aldehyde.
(iii)Brominationofphenolto2,4,6-tribromophenol
(iv)Benzyl alcohol to benzoic acid.
(v)Dehydration of propan-2-oI to propene.
(vi)Butan-2-one to butan-2-oL .

Q 22.

Write the equation of the reaction of hydrogen iodide with (i)1-propoxypropane (ii)methoxybenzene, and (iii)benzyl ethyl ether

Q 23.

Write the mechanism of the reaction of HI with methoxymethane.

Q 24.

What is the structure and IUPAC name of glycerol?

Q 25.

Arrange the following compounds in increasing order of acidity and give a suitable explanation:
Phenol, o-Nitrophenol, o-Cresol

Q 26.

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

Q 27.

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

Q 28.

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 29.

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 30.

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 31.

Identify aliylic alcohols in the above examples.

Q 32.

Write the equations involved in the following reactions:
(i) Reimer-Tiemann reaction
(ii) Kolbe's reaction

Q 33.

What is meant by hydroboration-oxidation reaction? Illustrate it with an example.

Q 34.

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

Q 35.

How is 1-propoxypropane synthesised from propan-l-ol? Write the mechanism of this reaction.

Q 36.

Mark the correct increasing order of reactivity of the following compounds with HBr/HCl.
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Q 37.

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

Q 38.

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

Q 39.

Alcohols react with active metals, e.g., Na, K, etc., to give corresponding alkoxides. Write down the decreasing order or reactivity of sodium metal towards primary, secondary and tertiary alcohols.

Q 40.

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

Q 41.

Explain why are low molecular mass alcohols soluble in water?

Q 42.

Explain why is p-nitrophenol more acidic than phenol?

Q 43.

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 44.

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

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.

Write IUPAC names of the following compounds:
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Q 47.

(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 48.

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

Q 49.

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.

Q 50.

Write the IUPAC name of the compound given below.
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