Solution of Chapter 11. Alcohols, Phenols and Ethers (Chemistry - Exemplar Book)

Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields.

How many alcohols with molecular formula C₄H₁₀O are chiral in nature?

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

A. 1° > 2° > 3°

B. 1° < 2° > 3°

C. 3° > 2° > 1°

D. 3° > 1° > 2°

CH₃CH₂OH can be converted into CH₃CHO by ______________.

The process of converting alkyl halides into alcohols involves_____________.

Which of the following compounds is aromatic alcohol?

(A)

(B)

(C)

(D)

Give IUPAC name of the compound given below.

IUPAC name of m-cresol is ___________.

IUPAC name of the compound

Which of the following species can act as the strongest base?

Which of the following compounds will react with sodium hydroxide solution in water?

Phenol is less acidic than ______________.

Which of the following is most acidic?

Mark the correct order of decreasing acid strength of the following compounds.

(a)

(b)

(c)

(d)

(e)

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

(a)

(b)

(c)

Arrange the following compounds in increasing order of boiling point.

Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol

Which of the following are used to convert RCHO into RCH₂OH?

Which of the following reactions will yield phenol?

Which of the following reagents can be used to oxidise primary alcohols to aldehydes?

Phenol can be distinguished from ethanol by the reactions with _________.

Which of the following are benzylic alcohols?

What is the structure and IUPAC name of glycerol?

Write the IUPAC name of the following compounds.

(A)

(B)

Write the IUPAC name of the compound given below.

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

What is denatured alcohol?

Suggest a reagent for the following conversion.

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

Suggest a reagent for conversion of ethanol to ethanal.

Suggest a reagent for conversion of ethanol to ethanoic acid.

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

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

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

Arrange the following compounds in increasing order of acidity and give a suitable explanation. Phenol, o-nitrophenol, o-cresol

Alcohols react with active metals e.g. Na, K etc. to give corresponding alkoxides.

Write down the decreasing order of reactivity of sodium metal towards primary, secondary and tertiary alcohols.

What happens when benzene diazonium chloride is heated with water?

Arrange the following compounds in decreasing order of acidity.

H₂O, ROH, HC ≡ CH

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

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

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

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

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

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

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

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

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

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?

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

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

Ethers can be prepared by Williamson synthesis in which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether can’t be prepared by this method. Explain.

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?

Explain why low molecular mass alcohols are soluble in water.

Explain why p-nitrophenol is more acidic than phenol.

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

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

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

Match the structures of the compounds given in Column I with the name of the compounds given in Column II.

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

Match the items of column I with items of column II.

Match the items of column I with items of column II.

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : Addition reaction of water to but-1-ene in acidic medium yields butan-1-ol

Reason : Addition of water in acidic medium proceeds through the formation of primary carbocation.

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : p-nitrophenol is more acidic than phenol.

Reason : Nitro group helps in the stabilisation of the phenoxide ion by dispersal of negative charge due to resonance.

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : IUPAC name of the compound is 2-Ethoxy-2-methylethane.

Reason : 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]

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : Bond angle in ethers is slightly less than the tetrahedral angle.

Reason : There is a repulsion between the two bulky (—R) groups.

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : Boiling points of alcohols and ethers are high.

Reason : They can form intermolecular hydrogen-bonding.

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : Like bromination of benzene, bromination of phenol is also carried out in the presence of Lewis acid.

Reason : Lewis acid polarises the bromine molecule.

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : o-Nitrophenol is less soluble in water than the m- and p-isomers.

Reason : m- and p- Nitrophenols exist as associated molecules.

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : Ethanol is a weaker acid than phenol.

Reason : Sodium ethoxide may be prepared by the reaction of ethanol with aqueous NaOH.

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : Phenol forms 2, 4, 6 – tribromophenol on treatment with Br2 in carbon disulphide at 273K.

Reason : Bromine polarises in carbon disulphide.

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion : Phenols give o- and p-nitrophenol on nitration with conc. HNO₃ and H₂SO₄ mixture.

Reason : —OH group in phenol is o–, p– directing.

Write the mechanism of the reaction of HI with methoxybenzene.

(a) Name the starting material used in the industrial preparation of phenol.

(b) Write complete reaction for the bromination of phenol in aqueous and non-aqueous medium.

(c) Explain why Lewis acid is not required in bromination of phenol?

How can phenol be converted to aspirin?

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