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

Classify the following as primary, secondary and tertiary alcohols:

Classify the following as primary, secondary and tertiary alcohols:

H₂C = CH – CH₂OH

Classify the following as primary, secondary and tertiary alcohols:

CH₃ – CH₂ – CH₂ – OH

Classify the following as primary, secondary and tertiary alcohols:

Classify the following as primary, secondary and tertiary alcohols:

Classify the following as primary, secondary and tertiary alcohols:

Identify allylic alcohols in the above examples.

Name the following compounds according to IUPAC system.

(i)

(ii)

(iii)

(iv)

(v)

Show how are the following alcohols prepared by the reaction of a suitable Grignard reagent on methanal?

Show how are the following alcohols prepared by the reaction of a suitable Grignard reagent on methanal?

Write structures of the products of the following reactions:

Write structures of the products of the following reactions:

Write structures of the products of the following reactions:

Give structures of the products you would expect when each of the following alcohol reacts with

(a) HCl –ZnCl₂

(b) HBr and

(c) SOCl₂.

(i) Butan-1-or (ii) 2-Methylbutan-2-ol

Predict the major product of acid catalyzed dehydration of

(i) 1-methyl cyclohexanol and (ii) butan-1-ol

Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding phenoxide ions.

Write the equations involved in the following reactions:

Reimer - Tiemann reaction

Write the equations involved in the following reactions:

Kolbe’s reaction

Write the reactions of Williamson synthesis of 2-ethoxy-3-methyl pentane starting from ethanol and 3-methyl pentane-2-ol.

Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why?

(i)

(ii)

Predict the products of the following reactions:

CH₃ – CH₂ – CH₂ – O – CH₃ + HBr →

Predict the products of the following reactions:

Predict the products of the following reactions:

Predict the products of the following reactions:

Write IUPAC names of the following compounds:

Write IUPAC names of the following compounds:

Write IUPAC names of the following compounds:

Write IUPAC names of the following compounds:

Write IUPAC names of the following compounds:

Write IUPAC names of the following compounds:

Write IUPAC names of the following compounds:

Write IUPAC names of the following compounds:

Write IUPAC names of the following compounds:

Write IUPAC names of the following compounds:

C₆H₅–O–C₂H₅

Write IUPAC names of the following compounds:

C₆H₅–O–C₇H₁₅(n-)

Write IUPAC names of the following compounds:

Write structures of the compounds whose IUPAC names are as follows:

2-Methylbutan-2-ol

Write structures of the compounds whose IUPAC names are as follows:

1-Phenylpropan-2-ol

Write structures of the compounds whose IUPAC names are as follows:

3,5-Dimethylhexane –1, 3, 5-triol

Write structures of the compounds whose IUPAC names are as follows:

2,3 – Diethylphenol

Write structures of the compounds whose IUPAC names are as follows:

1 – Ethoxypropane

Write structures of the compounds whose IUPAC names are as follows:

2-Ethoxy-3-methylpentane

Write structures of the compounds whose IUPAC names are as follows:

Cyclohexylmethanol

Write structures of the compounds whose IUPAC names are as follows:

3-Cyclohexylpentan-3-ol

Write structures of the compounds whose IUPAC names are as follows:

Cyclopent-3-en-1-ol

Write structures of the compounds whose IUPAC names are as follows:

4-Chloro-3-ethylbutan-1-ol.

Classify the isomers of alcohols in question 3. (i) as primary, secondary and tertiary alcohols.

Explain why propanol has higher boiling point than that of the hydrocarbon, butane?

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

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

Give the structures and IUPAC names of monohydric phenols of molecular formula, C₇H₈O.

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

Give the equations of reactions for the preparation of phenol from cumene.

Write chemical reaction for the preparation of phenol from chlorobenzene.

Write the mechanism of hydration of ethene to yield ethanol.

You are given benzene, conc. H₂SO₄ and NaOH. Write the equations for the preparation of phenol using these reagents.

Show how will you synthesise:

1-phenylethanol from a suitable alkene.

Show how will you synthesise:

cyclohexylmethanol using an alkyl halide by an SN2 reaction.

Show how will you synthesise:

pentan-1-ol using a suitable alkyl halide?

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

Explain why is ortho nitrophenol more acidic than ortho methoxyphenol ?

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

Give equations of the following reactions:

Oxidation of propan-1-ol with an alkaline KMnO₄ solution.

Give equations of the following reactions:

Bromine in CS₂ with phenol.

Give equations of the following reactions:

Dilute HNO₃ with phenol.

Give equations of the following reactions:

Treating phenol with chloroform in presence of aqueous NaOH

Explain the following with an example.

Kolbe’s reaction.

Explain the following with an example.

Reimer-Tiemann reaction.

Explain the following with an example.

Williamson ether synthesis.

Explain the following with an example.

Unsymmetrical ether

Write the mechanism of acid dehydration of ethanol to yield ethene

How are the following conversions carried out?

Propene → Propane-2-ol.

How are the following conversions carried out?

Benzyl chloride → Benzyl alcohol.

How are the following conversions carried out?

Ethyl magnesium chloride → Propane-1-ol.

How are the following conversions carried out?

Methyl magnesium bromide → 2-Methylpropan-2-ol

Name the reagents used in the following reactions:

Oxidation of a primary alcohol to carboxylic acid.

Name the reagents used in the following reactions:

Oxidation of a primary alcohol to an aldehyde.

Name the reagents used in the following reactions:

Bromination of phenol to 2,4,6-tribromophenol.

Name the reagents used in the following reactions:

Benzyl alcohol to benzoic acid.

Name the reagents used in the following reactions:

Dehydration of propan-2-ol to propene.

Name the reagents used in the following reactions:

Butan-2-one to butan-2-ol.

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

Give IUPAC names of the following ethers:

Give IUPAC names of the following ethers:

CH₃OCH₂CH₂Cl

Give IUPAC names of the following ethers:

O₂N-C₆H₄-OCH₃(p)

Give IUPAC names of the following ethers:

CH₃ CH₂CH₂OCH₃

Give IUPAC names of the following ethers:

Give IUPAC names of the following ethers:

Write the names of reagents and equations for the preparation of the following ethers by Williamson’s synthesis:

1-Propoxypropane.

Write the names of reagents and equations for the preparation of the following ethers by Williamson’s synthesis:

Ethoxybenzene

Write the names of reagents and equations for the preparation of the following ethers by Williamson’s synthesis:

2-Methoxy-2-methylpropane

Write the names of reagents and equations for the preparation of the following ethers by Williamson’s synthesis:

1-Methoxyethane

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

How is 1-propoxypropane synthesized from propan-1-ol? Write mechanism of this reaction.

Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give reason.

Write the equation of the reaction of hydrogen iodide with:

1-propoxypropane

Write the equation of the reaction of hydrogen iodide with:

methoxybenzene and

Write the equation of the reaction of hydrogen iodide with:

benzyl ethyl ether.

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 the benzene ring.

Write the mechanism of the reaction of HI with methoxymethane.

Write equations of the following reactions:

Friedel-Crafts reaction – alkylation of anisole.

Write equations of the following reactions:

Nitration of anisole.

Write equations of the following reactions:

Bromination of anisole in ethanoic acid medium.

Write equations of the following reactions:

Friedel-Craft’s acetylation of anisole.

Show how would you synthesise the following alcohols from appropriate alkenes?

Show how would you synthesise the following alcohols from appropriate alkenes?

Show how would you synthesise the following alcohols from appropriate alkenes?

Show how would you synthesise the following alcohols from appropriate alkenes?

When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place:

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.)