Q11.1 Write IUPAC names of the following compounds:

Solution

Q11.2 Write structures of the compounds whose IUPAC names are as follows:
(i) 2-Methylbutan-2-ol
(ii) 1-Phenylpropan-2-ol
(iii) 3,5-Dimethylhexane –1, 3, 5-triol
(iv) 2,3 – Diethylphenol
(v) 1 – Ethoxypropane
(vi) 2-Ethoxy-3-methylpentane
(vii) Cyclohexylmethanol
(viii) 3-Cyclohexylpentan-3-ol
(ix) Cyclopent-3-en-1-ol
(x) 4-Chloro-3-ethylbutan-1-ol.
Solution

Q11.3 (i) Draw the structures of all isomeric alcohols of molecular formula C₅H₁₂O and give their IUPAC names.
(ii) Classify the isomers of alcohols in question 11.3 (i) as primary, secondary and tertiary alcohols.
Solution

Q11.4 Explain why propanol has higher boiling point than that of the hydrocarbon, butane? Solution

Q11.5 Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.s Mention the factors that affect the rate of a chemical reaction Solution

Q11.6 What is meant by hydroboration-oxidation reaction? Illustrate it with an example. Solution

Q11.7 Give the structures and IUPAC names of monohydric phenols of molecular formula, C₇H₈O. Solution

Q11.8 While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile. Give reason. Solution

Q11.9 Give the equations of reactions for the preparation of phenol from cumene Solution

Q11.10 Write chemical reaction for the preparation of phenol from chlorobenzene Solution

Q11.11 Write the mechanism of hydration of ethene to yield ethanol. Solution

Q11.12 You are given benzene, conc. H₂SO₄ and NaOH. Write the equations for the preparation of phenol using these reagents. Solution

Q11.13 Show how will you synthesise:
(i) 1-phenylethanol from a suitable alkene. (ii) cyclohexylmethanol using an alkyl halide by an SN₂ reaction.
(iii) pentan-1-ol using a suitable alkyl halide?
Solution

Q11.14 Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that of ethanol. Solution

Q11.15 Explain why is ortho nitrophenol more acidic than ortho methoxyphenol ? Solution

Q11.16 Explain how does the –OH group attached to a carbon of benzene ring activate it towards electrophilic substitution? Solution

Q11.17 Give equations of the following reactions:
(i) Oxidation of propan-1-ol with alkaline KMnO₄ solution.
(ii) Bromine in CS₂ with phenol.
(iii) Dilute HNO₃ with phenol.
(iv) Treating phenol wih chloroform in presence of aqueous NaOH
Solution

Q11.18 Explain the following with an example.
(i) Kolbe’s reaction.
(ii) Reimer-Tiemann reaction.
(iii) Williamson ether synthesis.
(iv) Unsymmetrical ether Solution

Q11.19 Write the mechanism of acid dehydration of ethanol to yield ethene. Solution

Q11.20 How are the following conversions carried out?
(i) Propene → Propan-2-ol.
(ii) Benzyl chloride → Benzyl alcohol.
(iii) Ethyl magnesium chloride → Propan-1-ol.
(iv) Methyl magnesium bromide → 2-Methylpropan-2-ol.
Solution

Q11.21 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) Bromination of phenol to 2,4,6-tribromophenol.
(iv) Benzyl alcohol to benzoic acid.
(v) Dehydration of propan-2-ol to propene.
(vi) Butan-2-one to butan-2-ol.
Solution

Q11.22 Give reason for the higher boiling point of ethanol in comparison to methoxymethane. Solution

Q11.23 Give IUPAC names of the following ethers:

Solution

Q11.24 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
Solution

Q11.25 Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers. Solution

Q11.26 How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism of this reaction. Solution

Q11.27 Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give reason Solution

Q11.28 Write the equation of the reaction of hydrogen iodide with:
(i) 1-propoxypropane (ii) methoxybenzene and (iii) benzyl ethyl ether. Solution

Q11.29 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 benzene ring. Solution

Q11.30 Write the mechanism of the reaction of HI with methoxymethane. Solution

Q11.31 Write equations of the following reactions:
(i) Friedel-Crafts reaction – alkylation of anisole.
(ii) Nitration of anisole.
(iii) Bromination of anisole in ethanoic acid medium.
(iv) Friedel-Craft’s acetylation of anisole.
Solution

Q11.32 Show how would you synthesise the following alcohols from appropriate alkenes?

Solution

Q11.33 When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place:

Solution