I need to come up with a a separation and purification scheme procedure for 50% benzoic...

I need to come up with a a separation and purification scheme procedure for 50% benzoic acid, 40% benzoin, and 1,4-dibromobenzene having the following reagents available: 1M NaOH, 6M NaOH, 1M HCl, 6M HCl, 1M NaHCO3, saturated sodium chloride, diethyl ether, 95% ethanol, methanol, isopropyl alcohol, acetone, hexane, toluene, methylene chloride, and granular anhydrous sulfate

Expert Solution

Separation of Benzoic acid, Benzoin and 1,4-Dibromobenzene:

This mixture is dissolved in Diethyl ether solvent.

1) Benzoic acid

a) Separation: Given mixture treated with 1M NaHCO3 – a weak base. Benzoic acid get converted into the corresponding Sodium salt of Benzoic acid and get solvated in water. Benzoin – an alcohol and 1,4-Dibromobenzene – a neutral compound are not affected by this weak base 1M NaHCO3. Then with separatory funnel an aqueous phase containing salt of benzoic acid can be separated. Then the filtrate is treated with 1M HCl which regenerates benzoic acid back. The precipitated benzoic acid is filtered and filtrate again treated with 1M HCl to ensure complete removal of benzoic acid.

b) Purification: Benzoic acid thus obtained is dried under normal conditions and then recrystallization from 95 % ethanol or water gives purified benzoic acid.

2)Benzoin and 1,4-Dibromobenzene.

a) Separation can be done by solvent extraction method using Dichloromethane (DCM) i.e. Methylene chloride. Benzoin being more polar get into the DCM layer and 1,4-Dibromobenzene remains in Diethyl ether.

Extraction is repeated for 3-4 time to ensure complete removal of Benzoin.

Recrystalization of Benzoin: Recrystalized from hot methanol (Methylated spirit can be used). Benzoin is a pale yellow solid.

Recrystalization of 1,4-Dibromobenzene : can be recrystallized from toluene.

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queen_honey_blossom answered 1 year ago

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