Acid Strength and Reactions of Alcohols
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Powered by AIThe IUPAC name of the ortho-formylated product formed in the Reimer-Tiemann reaction of phenol is 2-hydroxybenzaldehyde or 2-hydroxybenzenecarbaldehyde .
The ease of dehydration of alcohols by the action of conc. H2SO4 is in the following order: (CH3)3C—OH > (CH3)2CH—OH > CH3CH2—OH. This is because tertiary alcohols form the most stable carbocations, followed by secondary and primary alcohols, making (CH3)3C—OH the most readily dehydrated .
When phenol reacts with bromine in carbon disulfide (Br₂/CS₂), an electrophilic aromatic substitution occurs where bromine is introduced at the ortho and para positions relative to the hydroxyl group on the benzene ring. This reaction results in the formation of 2,4,6-tribromophenol as a product, demonstrating the strong activating effect of the OH group that increases the ring's reactivity toward electrophiles .
Phenol undergoes electrophilic substitution reactions readily because the hydroxyl group (-OH) attached to the benzene ring significantly activates the ring. The -OH group increases the electron density particularly at the ortho and para positions due to its strong electron-donating effects through resonance. This increased electron density makes these positions more reactive toward electrophiles, hence the OH group is ortho, para-directing .
Phenol does not undergo protonation readily due to the resonance stabilization of the lone pair of electrons on the oxygen atom; this resonance reduces the availability of the lone pairs for bonding with a proton. In contrast, aliphatic alcohols do not have such delocalization, making their lone pairs more available for protonation .
The methyl group in cresol exerts an electron-releasing effect (+I effect), which decreases the acidity of cresol compared to phenol. This is because the phenoxide ion formed when cresol loses a hydrogen ion is less stabilized due to the electron-donating nature of the methyl group. As a result, phenol is a stronger acid than cresol .
Ethanol has a higher boiling point than methoxymethane because of hydrogen bonding between ethanol molecules. While methoxymethane can only engage in weaker dipole-dipole interactions, ethanol can form strong intermolecular hydrogen bonds due to the presence of the hydroxyl group, which increases the energy required to convert the liquid into gas, thus elevating its boiling point .
The correct order of acid strength is phenol (C₆H₅OH) > water (H₂O) > aliphatic alcohol (ROH). Phenol is the strongest acid in this comparison because the phenoxide ion formed upon losing a proton is resonance-stabilized. Water is more acidic than ROH because aliphatic alcohols have an electron-donating alkyl group, which reduces the stability of the alkoxide ion compared to the hydroxide ion .
The reaction mechanism utilized when an alkyl halide reacts with sodium alkoxide to form an ether is known as the Williamson synthesis. This mechanism is favored because it efficiently forms ethers through a nucleophilic substitution reaction, where the alkoxide ion acts as the nucleophile and attacks the electrophilic carbon in the alkyl halide, facilitating the formation of the C-O bond .
The increasing order of boiling points is (CH₃)₂NH < CH₃CH₂NH₂ < CH₃CH₂OH. This order is justified by the hydrogen bonding capabilities and molecular structures. Alcohols, such as CH₃CH₂OH, can form strong hydrogen bonds due to the presence of an -OH group, resulting in higher boiling points. Primary amines like CH₃CH₂NH₂ also form hydrogen bonds but less effectively than alcohols, whereas secondary amines like (CH₃)₂NH form even weaker hydrogen bonds due to steric hindrance .