Explain by giving the example of chlorobenzene that chlorine is ortho- and para-directing in electrophilic aromatic substitution reactions.
Step 1: Electrophilic Substitution in Chlorobenzene:
Chlorine has a \(-I\) effect (electron-withdrawing) and a \(+M\) effect (electron-donating via resonance), making the ortho and para positions more reactive.
Step 2: Example - Nitration of Chlorobenzene: \[ C_6H_5Cl + HNO_3 \xrightarrow{H_2SO_4} o-C_6H_4ClNO_2 + p-C_6H_4ClNO_2 \]
Give the structures of A, B, and C in the following reaction sequences:
(i) \(\mathrm{CH_3CH_2I} \xrightarrow[\ ]{\mathrm{NaCN}} A \xrightarrow[\ ]{\;\;HO^-\;/\;H_2O\;\;} B \xrightarrow[\;Br_2/NaOH\;]{} C\)
(ii) \(\mathrm{C_6H_5N_2^+Cl^-} \xrightarrow[\ ]{\mathrm{CuCN}} A \xrightarrow[\ ]{\;H_3O^+\;} B \xrightarrow[\ \Delta\ ]{\;NH_3\;} C\)
(iii) \(\mathrm{CH_3CH_2Br} \xrightarrow[\ ]{\mathrm{KCN}} A \xrightarrow[\ ]{\mathrm{LiAlH_4}} B \xrightarrow[\;273\,K\;]{\;HNO_2\;} C\)
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