Question

Based off the experiment of Bromination of aromatic compounds:

In a 10mL round bottom flask benzene and toluene are mixed and a small amount is removed for testing on GC, to the remaining mixture Bromine and iron filings are added. The reaction was refluxed and after initial reaction subsides the mixture was headed until red vapours were no longer present. After refluxing the reaction and mixture cooled it was transferred it into a test tube. 1 mL of 1 M NaOH was used to extract, a Vortex mixer thoroughly mixed the two layers. After allowing the layers to separate, the aqueous layer was removed. The organic layer was then washed with two separate 1 mL portions of water. The organic layer was then dried with some anhydrous magnesium sulphate. The product mixture in this experiment will be analyzed using gas chromatography. Four peaks were observed, one each for benzene, toluene, bromobenzene and the bromotoluenes!

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Present and discuss the mechanisms (for all possible products) for these reactions and account for the difference in reactivity between benzene and toluene.

Based on the mechanisms, would you predict that the bromotoluene product is primarily the meta isomer, or a mixture of the ortho and para isomers?

Answer 1

The answer are written as follows.

See the answers as above.