Synthesis of 1-Bromobutane from 1-Butanol
Synthesis of 1-Bromobutane from 1-Butanol
Reference: Discovering Organic Chemistry in the Laboratory; John R. Ganson Ph. D, Revised 2011 by Alfredo Mellace Ph. D www.Aldrich.com Purpose: To synthesize 1-bromobutane from 1-butanol via SN2 reaction. Alcohols are converted into the alkyl halides adding an aqueous solution sodium bromide. The sulfuric acid acts as a catalyst in converting the OH functional group of butanol, to a better leaving group. In order for this reaction to synthesis 1-Bromobutane, four major methods refluxing, simple distillation, separation, and gravity filtration needs to be performed.
Chemical Reaction:
NaBr, H2SO4
NaBr, H2SO4 Apparatus:
Table of Physical Constants and Reagents: Name | MW | Grams Used | Moles | Density g/mL @ 25°C | Boiling Point°C | Melting Point °C | 1-Butanol | 74.12 | 10ml | | .810 | 116-118 | | Sodium Bromide | 102.89 | 14g | .1361 | | | 755 | Sodium Bisulfite | 126.04 | 5mg | | | | 58.5 | Sulfuric Acid | 98.08 | | | 1.840 | 290 | | Potassium Carbonate (aq) | 138.21 | | | 2.29 | | 891 | Calcium Chloride | 110.98 | 1g | | | | 772 | 10% Silver Nitrate (aq) | 169.87 | 5 drops | | 4.35 | 444 | | Methanol | 32.04 | 1mL | | .791 | 64.7 | | Sodium Iodide in Acetone | | | | | | |
Experimental Procedure:
Macro/Miniscale Synthesis * 100ml round bottom flask, add 14g of NaBr, 15ml of water and 10ml of 1-butanol * Place the flask in an ice-water bath * Make the contents cold * Add 12ml of sulfuric acid slowly while swirling * Place the flask on a heating mantle over a stirring plate and clamp it securely * Add a stir bar or boiling chips to the flask to even out temperature * Connect the reflux condenser and gently reflux for around 45 minutes (boiling) * Approaching the 45 minutes, 1-bromobutane begins to separate, with a yellowish/clear top layer in the round bottom flask * Once the reflux is complete, allow boiling to settle
Reference: Discovering Organic Chemistry in the Laboratory; John R. Ganson Ph. D, Revised 2011 by Alfredo Mellace Ph. D www.Aldrich.com Purpose: To synthesize 1-bromobutane from 1-butanol via SN2 reaction. Alcohols are converted into the alkyl halides adding an aqueous solution sodium bromide. The sulfuric acid acts as a catalyst in converting the OH functional group of butanol, to a better leaving group. In order for this reaction to synthesis 1-Bromobutane, four major methods refluxing, simple distillation, separation, and gravity filtration needs to be performed.
Chemical Reaction:
NaBr, H2SO4
NaBr, H2SO4 Apparatus:
Table of Physical Constants and Reagents: Name | MW | Grams Used | Moles | Density g/mL @ 25°C | Boiling Point°C | Melting Point °C | 1-Butanol | 74.12 | 10ml | | .810 | 116-118 | | Sodium Bromide | 102.89 | 14g | .1361 | | | 755 | Sodium Bisulfite | 126.04 | 5mg | | | | 58.5 | Sulfuric Acid | 98.08 | | | 1.840 | 290 | | Potassium Carbonate (aq) | 138.21 | | | 2.29 | | 891 | Calcium Chloride | 110.98 | 1g | | | | 772 | 10% Silver Nitrate (aq) | 169.87 | 5 drops | | 4.35 | 444 | | Methanol | 32.04 | 1mL | | .791 | 64.7 | | Sodium Iodide in Acetone | | | | | | |
Experimental Procedure:
Macro/Miniscale Synthesis * 100ml round bottom flask, add 14g of NaBr, 15ml of water and 10ml of 1-butanol * Place the flask in an ice-water bath * Make the contents cold * Add 12ml of sulfuric acid slowly while swirling * Place the flask on a heating mantle over a stirring plate and clamp it securely * Add a stir bar or boiling chips to the flask to even out temperature * Connect the reflux condenser and gently reflux for around 45 minutes (boiling) * Approaching the 45 minutes, 1-bromobutane begins to separate, with a yellowish/clear top layer in the round bottom flask * Once the reflux is complete, allow boiling to settle