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Free Radical Chain Reaction Lab

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Free-Radical Chain Reactions: Bromination of Arenes Post Lab Report Reference: Experimental Organic Chemistry: A Miniscale and Microscale Approach 6th ed., by Gilbert and Martin, Chapter 9 Discussion: The purpose of the experiment as to explore how different hydrogen functional groups in hydrocarbons react with bromine through free-radical chain substitution. The product is dependent on the type of hydrogen that is being subjected to the bromination, whether that be aliphatic, allylic, benzylic, vinylic, acetylenic, or aromatic. By comparing the relative reactivity rates between the different hydrogens to bromine, a hypothesized ranking of reactivity was made of the provided hydrocarbons: toluene, ethyl benzene, tert-butylbenzene, cyclohexane, and methylcyclohexane. This hypothesis was then tested during the actual lab period by preparing two sets of reactions for each hydrocarbon: one in light and one in dark. Observations were noted throughout a thirty minute period in order to determine the experimental order of reactivity. Free-radical chain reactions are one of the few mechanisms that allow for functional …show more content…

Ethylbenzene was predicted to react first due to the secondary benzylic hydrogens present, the most reactive hydrogen for the three main hydrogen functional group classifications. Toluene contains primary benzylic hydrogens, the second most reactive hydrogen. Tert-butylbenzene contains primary aliphatic hydrogens but also an arene ring, allowing for aromatic hydrogens to also be present. This is why it was ranked above methylcyclohexane in the original proposed ranking. Methylcyclohexane contains tertiary, secondary and primary aliphatic hydrogens. Cyclohexane contains just secondary aliphatic hydrogens, justifying its place as the slowest of the hypothesized ranking

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