Revision Notes for JEE Chemistry: Alcohols Phenols And Ethers
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Classification and Nomenclature of Alcohols
Alcohols contain an -OH group on a saturated sp3 carbon. They are called primary, secondary or tertiary when the carbon carrying -OH is attached to one, two or three other carbon atoms. Dihydric alcohols such as ethane-1,2-diol (glycol) and the trihydric alcohol propane-1,2,3-triol (glycerol) have two or three -OH groups.
In IUPAC naming, the longest chain containing the carbon with -OH is chosen, the suffix -ol is added and the chain is numbered so that -OH gets the lowest number, e.g. \( \ce{CH3CH(OH)CH2CH3} \) is butan-2-ol.
Methods of Preparation
| Method | Reaction |
|---|---|
| Hydration of alkenes | \( \ce{CH2=CH2 + H2O ->[H+] CH3CH2OH} \) (Markovnikov addition) |
| Hydroboration-oxidation | alkene + \( \ce{B2H6} \), then \( \ce{H2O2/OH-} \) gives anti-Markovnikov alcohol |
| Hydrolysis of alkyl halides | \( \ce{RX + aq. KOH -> ROH + KX} \) |
| Reduction of aldehydes and ketones | \( \ce{NaBH4} \) or \( \ce{LiAlH4} \) gives primary and secondary alcohols |
| Reduction of acids and esters | \( \ce{LiAlH4} \) gives primary alcohols |
| Grignard reagents | HCHO gives a primary alcohol, other aldehydes secondary, ketones tertiary |
| From primary amines | \( \ce{RNH2 + HNO2 -> ROH + N2 + H2O} \) |
Methanol is made industrially from synthesis gas (\( \ce{CO + 2H2 ->[ZnO-Cr2O3] CH3OH} \)) and ethanol by fermentation of sugars using zymase of yeast.
Physical Properties
Alcohols have much higher boiling points than hydrocarbons, ethers or haloalkanes of similar mass because of intermolecular hydrogen bonding. Among isomers, boiling point falls with branching because surface area decreases. The lower alcohols (up to C3) and tert-butyl alcohol are completely miscible with water through hydrogen bonding, and solubility falls as the hydrocarbon part grows.
Chemical Reactions of Alcohols
The reactions fall into two groups: those that break the O-H bond (acidic behaviour, esterification) and those that break the C-O bond (substitution and elimination).
| Reagent | Product |
|---|---|
| Na | alkoxide and \( \ce{H2} \); acidity order: methanol greater than primary, then secondary, then tertiary |
| HX / Lucas reagent | alkyl halide; rate tertiary greater than secondary greater than primary |
| \( \ce{PCl5} \), \( \ce{SOCl2} \), \( \ce{PBr3} \) | alkyl halide |
| conc. \( \ce{H2SO4} \), 170 degrees C | alkene (dehydration, Saytzeff's rule) |
| conc. \( \ce{H2SO4} \), 140 degrees C | ether (bimolecular dehydration) |
| carboxylic acid with \( \ce{H+} \) | ester (Fischer esterification) |
| \( \ce{Cu} \), 573 K | primary gives aldehyde, secondary gives ketone, tertiary gives alkene |
Oxidising agents such as acidified \( \ce{K2Cr2O7} \) convert primary alcohols to aldehydes and then acids, and secondary alcohols to ketones. PCC stops at the aldehyde stage. Tertiary alcohols resist oxidation under mild conditions.
Distinguishing Tests for Alcohols
| Test | Primary | Secondary | Tertiary |
|---|---|---|---|
| Lucas reagent | no turbidity at room temperature | turbidity in about 5 minutes | immediate turbidity |
| Victor Meyer test | red colour | blue colour | colourless |
| Chromic acid (orange) | turns green | turns green | no change |
| Iodoform test | only ethanol | only \( \ce{CH3CH(OH)R} \) types | negative |
Vicinal diols such as glycol and glycerol are cleaved by periodic acid (\( \ce{HIO4} \)) or lead tetraacetate between the two carbons carrying -OH.
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