Hydroxy compounds

• Nucleophilic substitution to form R-X from alcohol:

  • conc. HCl, ZnCl2 catalyst, heat

  OR

  • HBr/HI (g), rtp
• nucleophilic substitution to form R-X from alcohol:

  • anhydrous PX3, heat

  side products: H3PO3 (l)
• nucleophilic substitution to form R-Cl from alcohol:

  • anhydrous PCl5, rtp

  side products: POCl3 (l), HCl (g)
• Nucleophilic substitution to form R-Cl from alcohol:

  • anhydrous SOCl2, heat

  side products: SO2 (g), HCl (g)
• oxidation of primary alcohol to form aldehyde:

  • K2Cr2O7 (aq), H2SO4 (aq), immediate distil
• Oxidation to form Carboxylic acid from primary alcohol:

  • K2Cr2O7 (aq), H2SO4 (aq), heat

  OR

  • KMnO4 (aq), H2SO4 (aq), heat
• Oxidation to form ketone from secondary alcohols:

  K2Cr2O7 (aq), H2SO4 (aq), heat

  OR

  • KMnO4 (aq), H2SO4 (aq), heat
• To test for this group:

  • iodine, NaOH (aq), heat

  forms carboxylate salt, CHI3 (yellow ppt), NaI

  
• redox reaction between alcohol and Na(s) forms hydrogen gas and RO-Na+
• condensation/nucleophilic acyl substitution to form esters

  • alcohol and acid, with concentrated H2SO4 as catalyst heat
  • alcohol and acyl chloride, rtp
• Phenols can react with Na(s) in a redox reaction to form hydrogen gas and phenoxide salt
• phenol can react with NaOH (aq) to form phenoxide salt in acid-base reaction
• Phenols can react with Br2 (aq), at rtp to form 2,4,6-tribromophenol, electrophilic substitution reaction
• phenols can react with Br2 in CCl4, rtp, to form 2-bromophenol or 4-bromophenol in electrophilic substitution reaction
• phenol can react with concentrated HNO3 at rtp to form 2,4,6-nitrophenol in an electrophilic substitution reaction
• phenol can react with dilute HNO3 at rtp to form 2-nitrophenol or 4-nitrophenol in an electrophilic substitution reaction
• Phenols can react with sodium carbonate in an acid-carbonate reaction to form phenoxide ion and sodium hydrogen carbonate