Alcohols, Phenols and Ethers name reactions

Name reactions

Reimer-Tiemann reaction

$\displaystyle \text{C}_6\text{H}_5\text{OH} \xrightarrow[\text{then H}^+]{\text{CHCl}_3,\ \text{aq. NaOH}} \text{salicylaldehyde}$

Kolbe's reaction

$\displaystyle \text{C}_6\text{H}_5\text{OH} \xrightarrow[\text{then H}^+]{\text{NaOH, then CO}_2} \text{salicylic acid}$

Williamson synthesis

$\displaystyle \text{R-X} + \text{R'-ONa} \rightarrow \text{R-O-R'} + \text{NaX}$

Use a primary alkyl halide, since tertiary ones eliminate.

Esterification

$\displaystyle \text{ROH} + \text{R'COOH} \underset{}{\overset{\text{H}^+}{\rightleftharpoons}} \text{R'COOR} + \text{H}_2\text{O}$

Dehydration

$\displaystyle \text{CH}_3\text{CH}_2\text{OH} \xrightarrow[443\ \text{K}]{\text{conc. H}_2\text{SO}_4} \text{CH}_2\text{=CH}_2 + \text{H}_2\text{O}$

Tests and trends

• Lucas test separates alcohols: tertiary turns cloudy immediately, secondary in about five minutes, and primary not at room temperature.
• Phenol gives a violet colour with neutral FeCl₃.
• Phenol is more acidic than alcohols because its phenoxide ion is stabilised by resonance.
• Electron-withdrawing groups such as −NO₂ make phenol more acidic, and electron-donating groups make it less so.