Chemistry

Alcohols, Phenols and Ethers

Question:

Write the mechanism of the reaction of HI with methoxybenzene.

Answer:

In case of alkyl aryl ethers, the products are always phenol and an alkyl halide because due to resonance C6H5 – O bond has partial double bond character.
ncert-exemplar-problems-class-12-chemistry-alcohols-phenols-ethers-59

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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.

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 3.

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 4.

Suggest a reagent for conversion of ethanol to ethanal.

Q 5.

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

Q 6.

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

Q 7.

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

Q 8.

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 9.

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 10.

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

Q 11.

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

Q 12.

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 13.

Identify aliylic alcohols in the above examples.

Q 14.

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

Q 15.

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 16.

What is denatured alcohol?

Q 17.

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

Q 18.

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

Q 19.

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 20.

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 21.

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

Q 22.

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

Q 23.

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

Q 24.

Write the mechanism of the reaction of HI with methoxybenzene.

Q 25.

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 26.

Give IUPAC names of the following ethers.
ncert-solutions-for-class-12-chemistry-alcohols-phenols-and-ether-29

Q 27.

Illustrate with examples the limitations of Willamson synthesis for the preparation of certain types of ethers.

Q 28.

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

Q 29.

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

Q 30.

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

Q 31.

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 32.

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 33.

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

Q 34.

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 35.

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

Q 36.

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

Q 37.

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
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Q 38.

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

Q 39.

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

Q 40.

Write the mechanism of the reaction of HI with methoxymethane.

Q 41.

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

Q 42.

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 43.

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 44.

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

Q 45.

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

Q 46.

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

Q 47.

Explain why are low molecular mass alcohols soluble in water?

Q 48.

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

Q 49.

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

Q 50.

How can phenol be converted to aspirin?