Please help me with this separation scheme. Thanks. In the reaction shown below,

Question

Please help me with this separation scheme. Thanks.

In the reaction shown below, 1-hexene is reacted with a solution of 30% hydrobromic acid in acetic acid to form 1-bromohexane and 2-bromohexane. The products shown are liquid at room temperature. Devise a separation scheme to isolate the products together from the reaction mixture. Assume that 1-hexene is the limiting reagent and has a lower boiling point than the two products. you do not need to separate the two products (1-bromohexane and 2-bromohexane) from one another. Below is a list of reagents available in lab. You may use any of these given reagents (e.g., acids, bases) as needed in your separation scheme and you also have access to a solvent evaporator if a solvent must be evaporated, and a filtration apparatus to filter. Be specific with each reagent name and technique used in your separation scheme. The most efficient separation scheme will receive the most credit.

Explanation / Answer

Since the boiling point of alkene is lower than products it may be separated by fractional distillation.

The other reagents HBr and CH3COOH are soluble in water hence they can be extracted with dil. NaHCO3 or dil. NaOH and products with ether.

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