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Reactivity Order of Hydrogen Atoms on Propylbenzene

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C6H5(CH2CH2CH3) + (CH3)3COOCl
-----> C6H5(CHClCH2CH3) (65%) +C6H5(CH2CHClCH3) (25%) + C6H5(CH2CH2CH2Cl) (10%)

1. Refer to above reaction. When propylbenzene reacts with tert-butylhypochlorite three monochlorinated products are formed in the ratios indicated. Calculate a reactivity order for each type of hydrogen atom in propylbenzene.
2. Explain why (1-chloropropyl) benzene is the major product of this reaction.
3. Will the product mixture of this reaction display optical activity?

keywords: 1-propylbenzene, phenylpropane, 1-phenylpropane

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Solution Summary

This solution illustrates how to calculate the reactivity order of the hydrogens in propylbenzene using its reaction with t-butyl hypochlorite and the percentages of the chloropropylbenzenes formed. Reactivity and optical activity of the products are also discussed.

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