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Free-Radical Halogenation Lab Report

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Introduction: In this laboratory, free-radical halogenation was used in order to brominate compounds such as toluene, ethylbenzene, isopropylbenzene and t-butylbenzene (structures as seen below). Free-radical halogenation consists of a halogen, connected through sigma bonding, breaking and interacting with the side chain of the aromatic compound. The three steps in the process of halogenation take place in the presence of light and are labeled as initiation, propagation and termination. Initiation being the breaking of the sigma bond between the diatomic halogen, propagation being the interaction of hydrogen, carbon and the radical itself, and termination which is the recombination of stable molecules.

Toluene:

Ethylbenzene:

Isopropylbenzene:

t-butylbenzene

The purpose of this lab was to observe the speed at which the process of halogenation took place in molecules with carbons of varying stature …show more content…
This implies that secondary carbons (those attached to two hydrogens) react the fastest, followed by tertiary (attached to one hydrogen), primary (three hydrogens) and ending with quaternary carbons (no hydrogens attached). When critically thinking about these findings, they appear irrational due to the inconsistency in trend and therefore must have come into contact with some form of error. This being said, one could make the assumption that the data could have gone one of two ways. One option would be for isopropylbenzene to be the most reactive and toluene to be the least reactive (not taking the unreactive, t-butylbenzene, into consideration). The second option would be just the opposite with toluene reacting the fastest and isopropylbenzene the

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