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Addition of bromine to hydrocarbons

left glass orange liquid, right glass clear liquid

Does liquid bromine react with either cyclohexane or cyclohexene?

cyclohexane left, bromine in middle and cyclohexene on right

The glass on the left contains cyclohexane, an alkane with the formula C6H12. The glass on the right contains cyclohexene, an alkene which has the formula C6H10.

Click on the small picture to see the video.

thumbnail  pouring bromine into liquid

An addition reaction occurs when halogens are added to alkenes, but not to alkanes. The following reaction occurs when Br2 is added to cyclohexene:

C6H10 + Br2 ----> C6H10Br2

One bromine atom adds to each side of the double bond, which opens to form two new single bonds. You can see the reaction occur because the red color of Br2disappears as it forms the colorless alkyl halide.

Bromine is not able to react with cyclohexane by substitution, and there are no double bonds for an addition reaction, so no reaction occurs:

C6H12 + Br2 ----> N.R.

You can tell that no reaction has occurred because the red color of Br2 remains.

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Chemistry at Illinois University of Illinois at Urbana-Champaign