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Recall the reactions (reagents and conditions) by which alcohols can be produced: (a) electrophilic addition of steam to an alkene, H₂O(g) with H₃PO₄ catalyst; (b) reaction of alkenes with cold dilute acidified potassium manganate(VII) to form a diol; (c) substitution of a halogenoalkane using NaOH(aq) and heat; (d) reduction of an aldehyde or ketone using NaBH₄ or LiAlH₄; (e) reduction of a carboxylic acid using LiAlH₄; (f) hydrolysis of an ester using dilute acid or dilute alkali and heat.
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Describe: (a) the reaction with oxygen (combustion); (b) substitution to form halogenoalkanes, e.g. by reaction with HX(g); or with KCl and concentrated H₂SO₄ or concentrated H₃PO₄; or with PCl₃ and heat; or with PCl₅; or with SOCl₂; (c) the reaction with Na(s); (d) oxidation with acidified K₂Cr₂O₇ or acidified KMnO₄ to (i) carbonyl compounds by distillation and (ii) carboxylic acids by refluxing; (e) dehydration to an alkene, using a heated catalyst, e.g. Al₂O₃, or a concentrated acid; (f) formation of esters by reaction with carboxylic acids with concentrated H₂SO₄ as catalyst, as exemplified by ethanol.
For (d): primary alcohols give aldehydes, which can be further oxidised to carboxylic acids; secondary alcohols give ketones; tertiary alcohols cannot be oxidised.
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(a) Classify alcohols as primary, secondary and tertiary, including examples with more than one alcohol group; (b) state characteristic distinguishing reactions, e.g. mild oxidation with acidified K₂Cr₂O₇, with a colour change from orange to green.
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Deduce the presence of a CH₃CH(OH)– group in an alcohol, CH₃CH(OH)–R, from its reaction with alkaline I₂(aq) to form a yellow precipitate of tri-iodomethane and an ion, RCO₂⁻.
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Explain the acidity of alcohols compared with water.
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