Synthesis of 1-Bromobutane from 1-Butanol

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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 and...
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