Chemistry

Alcohols, Phenols and Ethers

Question:

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

Answer:

(c) Compound (A) i.e., phenol and compound (D) i.e., a derivative of phenol cannot be considered as aromatic alcohol. As phenol is also known as, carbolic acid cannot be considered as aromatic alcohol.
Compound (B) and (C), -OH group is bonded to sp3 hybridised carbon which in turn is bonded to benzene ring.

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Alcohols, Phenols and Ethers

Q 1.

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 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.

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.

Q 4.

IUPAC name of the compound
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-10

Q 5.

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

Q 6.

What is denatured alcohol?

Q 7.

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

Q 8.

Match the starting materials given in Column I with the products formed by these (Column II) in the reaction with HI.
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-50
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-51

Q 9.

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

Q 10.

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 11.

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

Q 12.

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

Q 13.

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

Q 14.

Write the mechanism of the reaction of HI with methoxybenzene.

Q 15.

Write IUPAC names of the following compounds:
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-1
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-2
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-3

Q 16.

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

Q 17.

Show how would you synthesise the following alcohols from appropriate alkanes?
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-42

Q 18.

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 19.

What is the correct order of reactivity of alcohols in the following reaction?
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-3

Q 20.

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

Q 21.

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

Q 22.

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

Q 23.

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.

Q 24.

Explain why is p-nitrophenol more acidic than phenol?

Q 25.

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

Q 26.

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

Q 27.

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 28.

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

Q 29.

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 30.

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

Q 31.

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

Q 32.

Explain why are low molecular mass alcohols soluble in water?

Q 33.

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

Q 34.

How can phenol be converted to aspirin?

Q 35.

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

Q 36.

Write the mechanism of hydration of ethene to yield ethanol.

Q 37.

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 38.

Write the mechanism of the reaction of HI with methoxymethane.

Q 39.

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

Q 40.

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

Q 41.

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?

Q 42.

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

Q 43.

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 44.

Write chemical reaction for the preparation of phenol from chlorobenzene.

Q 45.

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

Q 46.

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

Q 47.

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 48.

What is the structure and IUPAC name of glycerol?

Q 49.

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

Q 50.

Suggest a reagent for the following conversion.
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-28