8.17 Complete each synthesis by giving missing starting material, reagent or products

7.10 HBr C2 H5 OH C2 H5 Br CH3 – CH2 – CH – CH – ONa + C 2H5 Br CH3 – CH2 – CH – CH – OC2 H5 CH3 CH3 CH3 CH3 2-Ethoxy-3-methylpentane 225 Alcohols, Phenols and Ethers Reprint 2025-26

7.12 Predict the products of the following reactions: (i) CH3 − CH2 − CH2 − O – CH3 + HBr → (ii) (iii) (iv) ( CH 3 ) 3 C − OC 2 H5 HI → SummarySummarySummarySummarySummary Alcohols and phenols are classified (i) on the basis of the number of hydroxyl groups and (ii) according to the hybridisation of the carbon atom, sp 3 or sp 2 to which the –OH group is attached. Ethers are classified on the basis of groups attached to the oxygen atom. Alcohols may be prepared (1) by hydration of alkenes (i) in presence of an acid and (ii) by hydroboration-oxidation reaction (2) from carbonyl compounds by (i) catalytic reduction and (ii) the action of Grignard reagents. Phenols may be prepared by (1) substitution of (i) halogen atom in haloarenes and (ii) sulphonic acid group in aryl sulphonic acids, by –OH group (2) by hydrolysis of diazonium salts and (3) industrially from cumene. Alcohols are higher boiling than other classes of compounds, namely hydrocarbons, ethers and haloalkanes of comparable molecular masses. The ability of alcohols, phenols and ethers to form intermolecular hydrogen bonding with water makes them soluble in it. Alcohols and phenols are acidic in nature. Electron withdrawing groups in phenol increase its acidic strength and electron releasing groups decrease it. Alcohols undergo nucleophilic substitution with hydrogen halides to yield alkyl halides. Dehydration of alcohols gives alkenes. On oxidation, primary alcohols yield aldehydes with mild oxidising agents and carboxylic acids with strong oxidising agents while secondary alcohols yield ketones. Tertiary alcohols are resistant to oxidation. The presence of –OH group in phenols activates the aromatic ring towards electrophilic substitution and directs the incoming group to ortho and para positions due to resonance effect. Reimer-Tiemann reaction of phenol yields salicylaldehyde. In presence of sodium hydroxide, phenol generates phenoxide ion which is even more reactive than phenol. Thus, in alkaline medium, phenol undergoes Kolbe’s reaction. Ethers may be prepared by (i) dehydration of alcohols and (ii) Williamson synthesis. The boiling points of ethers resemble those of alkanes while their solubility is comparable to those of alcohols having same molecular mass. The C–O bond in ethers can be cleaved by hydrogen halides. In electrophilic substitution, the alkoxy group activates the aromatic ring and directs the incoming group to ortho and para positions. 221 Alcohols, Phenols and Ethers Reprint 2025-26 Exercises 7.1 Write IUPAC names of the following compounds: (i) (ii) (iii) (iv) (v) (vi) (vii) (viii) (ix) (x) C6H5–O–C2H5 (xi) C6H5–O–C7H15(n–) (xii) 7.2 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. 7.3 (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. 7.4 Explain why propanol has higher boiling point than that of the hydrocarbon, butane? 7.5 Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact. 7.6 What is meant by hydroboration-oxidation reaction? Illustrate it with an example. 7.7 Give the structures and IUPAC names of monohydric phenols of molecular formula, C7H8O. 7.8 While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile. Give reason. 7.9 Give the equations of reactions for the preparation of phenol from cumene. 7.10 Write chemical reaction for the preparation of phenol from chlorobenzene. 7.11 Write the mechanism of hydration of ethene to yield ethanol. 7.12 You are given benzene, conc. H2SO4 and NaOH. Write the equations for the preparation of phenol using these reagents. Chemistry 222 Reprint 2025-26