Make Alkyl Halides Bromoethane and Bromohexane

In this video we make the alkyl halides bromoethane and bromohexane by nucleophilic substitution of alcohol under acidic conditions.

the highest yielding method is to use alcohol with hydrobromic acid and sulfuric acid. To make bromoethane 350g of 48% hydrobromic acid, 120mL of ethanol and 145mL of sulfuric acid were combined in a flask cooled in ice with plenty of time between additions to allow full cooling. The mixture was then gently heated to 40 degrees Celsius and slowly ramped to 70 Celsius to distill off the bromoethane that forms. What's happening is the classic Sn2 nucleophilic substitution reaction taught in basic organic chemistry. The alcohol is protonated by the acid conditions and essentially forms water still attached to the carbon backbone. Bromide ions come in and attack the carbon and the water leaves. This forms bromoethane. The bromohexane is washed with water and 5% sodium bicarbonate solutions before being dried with anhydrous magnesium sulfate.

Bromohexane is made in a similar fashion. 1 mole of 1-hexanol is mixed with 1.5 moles of sodium bromide and 2 moles of sulfuric acid. the mixture is refluxed for six hours and the bromohexane is recovered using a separatory funnel. it is then distilled and washed. Then fractionally distilled to remove water.

Related videos:
Make hydrobromic acid:    • Make Hydrobromic Acid  

Make Chloroform:    • Make chloroform by the haloform reaction  

Make chlororobenzyl chloride:    • Make p-chlorobenzyl chloride (from para-ch...  


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