In a 100mL round bottomed flask place a stir bar. 10g sodium bromide and 10mL of

Question

In a 100mL round bottomed flask place a stir bar. 10g sodium bromide and 10mL of water Stir for a few minutes to dissole some of the sodium bromide then add 10mL 1 -butanol. Add an ice bath under the mixture then slowly add 10mL sulfuric acid from a separatory tunnel with continuous stirring. Set-up the reflux apparatus and reflux for 45min begin counting after boiling. After the 45min, remove the reflux apparatus and add the simple distillation apparatus, ensure that the collection flask is on ice. Continue simple distillation to 115 degree C. Extract the distillate (what you collected) with the following: 10mL 5% sodium hydroxide 10mL of water 10mL saturated salt water keeping the organic layer each time. Organic layer will be on the bottom. After the final extraction dry the organic layer with sodium sulfate Once clear, decant to dried product to a tared round bottom and get the weight of the product Simple distill to record the boiling point Suggest a reason, based on the mechanism of the reaction, for the long reflux time. In other words, what is the rate limiting step? During the simple distillation to 115 degree C what else is collected besides the product? Besides checking densities, what is another method for determining which layer is organic?

Explanation / Answer

In this reaction first the -OH group is protonated by H2So4 to convert it to OH2+. The leaving group leaves to form a carbocation. This is the rate limiting step.

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During distillation at 115oC water is also collected with the product

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add a drop to the layer which you want to test. If the drop floats on the liquid surface , it is organic layer. If it mixes well , it is aqueous

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