Consider the following data for the nitration of monosubstituted benzene rings: | R- | Relative Rate | Percentage of Isomer | | | | :--- | :--- | :--- | :--- | :--- | | | | ortho | meta | para | | OH | 1000 | 40 | <2 | 58 | | CH3 | 25 | 58 | 4 | 38 | | Ph | 15 | 20 | <0.6 | 80 | | H | 1 | / | / | / | | CH2Cl | 0.71 | 32 | 15.5 | 52.5 | | Cl | 0.033 | 31 | <0.2 | 69 | | NO2 | 6 x 10^-8 | 5 | 53 | 2 | (a) Explain the trends of rates of reaction. (b) Explain the regiochemistry of the reactions. (c) Compare and contrast when R = CH3 vs when R = CH2Cl.
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When R = OH, the hydroxyl group is an electron-donating group (EDG), which increases the electron density on the benzene ring and makes it more reactive towards electrophilic aromatic substitution (EAS) reactions like nitration. This results in a higher relative Show more…
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