Chemistry

Alcohols, Phenols and Ethers

Question:

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?

Answer:

The C – O – H bond angle in alcohols is slightly less than the tetrahedral angle (109.5 °) because of larger repulsions between the lone pairs of electrons. For example in methanol C – O – H bond angle is 108.9 °.
In ethers, the C – O – C bond angle is slightly greater than tetrahedral angle. For example in dimethyl ether C – O – C bond angle is 111.7 °. The larger bond angle in ethers may be because of greater repulsions between bulkier alkyl groups as compared to one H in alcohols.

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Alcohols, Phenols and Ethers

Q 1.

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

Q 2.

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

Q 3.

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

Q 4.

What happens when benzene diazonium chloride is heated with water?

Q 5.

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 6.

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

Q 7.

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

Q 8.

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

Q 9.

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 10.

Explain why are low molecular mass alcohols soluble in water?

Q 11.

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 12.

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

Q 13.

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

Q 14.

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

Q 15.

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

Q 16.

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

Q 17.

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

Q 18.

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

Q 19.

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

Q 20.

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

Q 21.

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

Q 22.

Identify aliylic alcohols in the above examples.

Q 23.

Write the mechanism of the reaction of HI with methoxymethane.

Q 24.

Explain why is p-nitrophenol more acidic than phenol?

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.

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 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.

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

Q 29.

Suggest a reagent for conversion of ethanol to ethanal.

Q 30.

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

Q 31.

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 32.

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 33.

Write the mechanism of the reaction of HI with methoxybenzene.

Q 34.

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

Q 35.

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

Q 36.

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

Q 37.

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

Q 38.

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
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Q 39.

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 40.

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

Q 41.

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

Q 42.

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

Q 43.

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

Q 44.

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

Q 45.

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 46.

(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 47.

You are given benzene, cone. H2S04and NaOH. Write the equations for the preparation of phenol using these reagents.

Q 48.

How are the following conversions carried out?
(i) Propene —> Propan -2-ol
(ii) Benzyl chloride —> Benzyl alcohol
(iii) Ethyl magnesium chloride —> Propan-l-ol
(iv) Methyl magnesium bromide —> 2-Methylpropan-2-ol

Q 49.

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

Q 50.

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