ESTERS

Acetic acid + ethanol Methanol + Salicylic acid Ethanol + Benzoic acid Aliphatic Aromatic Ethyl acetate Methyl salicylateEthyl benzoate

Ethyl acetate Methyl salicylate Ethyl benzoate Physical properties: State Color Odor Inflammability Change in appearance Change in odor Color imparted to the flame Residue comment Liquid, oily, true Fruity odorVicks odor Colorless Ignition test: Inflammable, non luminous, non smoky No change Characteristic odor The compound is aliphatic Inflammable, luminous, smoky All volatilization No change No residue The compounds are aromatic

Miscibility: Ethyl acetate Ethyl acetate Methyl salicylate Methyl salicylate Ethyl benzoate H2OH2O L.p. Dil. HCl 10%NaOH Conc. H 2 SO 4 Comment: All immiscible.: All are neutral compounds All immiscible

Preliminary test: Ethyl acetate Ethyl acetate Methyl salicylate Methyl salicylate Ethyl benzoate Soda lime Soda lime 30% NaOH 30% NaOH On cold: On hot: FeCl 3 FeCl 3 On cold: On hot: Conc. H 2 SO 4 Conc. H 2 SO 4 On cold: On hot: Not done ( for solid only) Not done No reaction in all No reaction Violet color in ethanol layer White ppt of Na-salicylateNo reaction

General test : Ethyl acetate Ethyl acetate Methyl salicylate Methyl salicylate Ethyl benzoate Ethyl benzoate 1. Hydroxylamine HCl test: Ester + hydroxylamine HCl ((white solid)) + 10% NaOH until fussion clear solution after cooling + Dil. HCl + 2 drops FeCl 3 Reddish brown colorReddish violet colorReddish brown color 2. Hydrolysis test: 2 ml ester + 20ml 10% NaOH Reflux 30 min. Distillation Distillate (( alc.)) Residue (( acid)) Ethanol + Acetic acid Methanol + Salicylic acid Ethanol +Benzoic acid

Specific test : Ethyl acetate Ethyl acetate Methyl salicylate Methyl salicylate Ethyl benzoate Ethyl benzoate Ethyl acetate is lighter than H 2 O Ethyl acetate + H 2 O shaking Methyl salicylate+ H 2 O shaking Ethyl benzoate + H 2 O shaking Methyl salicylate is heavier than H 2 O Ethyl benzoate is heavier than H 2 O

IR LocationComment Ethyl acetate Ethyl acetate Methyl salicylate Ethyl benzoate Ethyl benzoate 1750 – 1735 cm -1 < 3000 cm -1 C=O stretching band 1750 – 1735 cm -1 CH aliphatic stretching band > 3000 cm -1 CH aromatic stretching band 1750 – 1735 cm -1 C=O stretching band < 3000 cm -1 CH aliphatic stretching band > 3000 cm -1 CH aromatic stretching band 3400 – 3200 cm -1 -OH stretching band < 3000 cm -1