Chemistry

Alcohols, Phenols and Ethers

Question:

Write the mechanism of hydration of ethene to yield ethanol.

Answer:

Direct addition of H20 to ethene in presence of an acid does not occur. Indirectly, ethene is first passed through concentrated H2S04, when ethyl hydrogen sulphate is formed.
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-15

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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 are used to convert RCHO into RCH2OH?
(a) H2/Pd
(b) LiAlH4
(c) NaBH4
(d) Reaction with RMgX followed by hydrolysis

Q 5.

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

Q 6.

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 7.

Which of the following reaction will yield phenol?
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-18
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Q 8.

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 9.

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

Q 10.

Mark the correct order of decreasing acid strength of the following
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-13

Q 11.

What is the structure and IUPAC name of glycerol?

Q 12.

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

Q 13.

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

Q 14.

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

Q 15.

Write steps to carry out the conversion of phenol to aspirin.

Q 16.

Explain why are low molecular mass alcohols soluble in water?

Q 17.

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

Q 18.

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

Q 19.

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 20.

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

Q 21.

Suggest a reagent for conversion of ethanol to ethanal.

Q 22.

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

Q 23.

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 24.

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 25.

Predict the major product of acid catalysed dehydration of
(i) 1-nicthylcyclohcxanoland
(ii) butan-1-ol

Q 26.

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

Q 27.

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

Q 28.

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 29.

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

Q 30.

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 31.

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

Q 32.

Give IUPAC name of the compound given below.
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-7

Q 33.

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 34.

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

Q 35.

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

Q 36.

Assertion (A): Like bromination of benzene, bromination of phenol is also carried out in the presence of Lewis acid.
Reason (R): Lewis acid polarizes the bromine molecule.

Q 37.

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 38.

When 3-methylbutant 2-ol is treated with HBr, the following reaction takes place:
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-47
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.)

Q 39.

What is the correct order of reactivity of alcohols in the following reaction?
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Q 40.

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

Q 41.

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

Q 42.

Match the items of Column I with items of Column II.ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-52
 

Q 43.

How can phenol be converted to aspirin?

Q 44.

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

Q 45.

Which of the following is an appropriate set of reactants for the preparation of l-methoxy-4- nitrobenzene and why?
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-20

Q 46.

Write the mechanism of hydration of ethene to yield ethanol.

Q 47.

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

Q 48.

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

Q 49.

Write the IUPAC name of the following compounds,
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Q 50.

What is denatured alcohol?