Give the structural formula of cpd E and state the reaction conditions and the reagent of i .),ii.)to v.)

Compound C is formed from toluene (C7H8) by nitration ($\text{HNO}_3/\text{H}_2\text{SO}_4$). This yields nitrotoluene, primarily a mixture of 2-nitrotoluene and 4-nitrotoluene.
Compound E is formed from C (nitrotoluene) by reaction with $\text{Sn/HCl}$ or $\text{Fe/HCl}$. This is a reduction reaction that converts a nitro group ($\text{-NO}_2$) to an amino group ($\text{-NH}_2$).
Assuming C is 4-nitrotoluene (a common major product), then E would be 4-aminotoluene (p-toluidine).

The structural formula of E is:

Specifically:

      CH3
     /   \
    C-----C
   //     \\
  C       C
   \\     //
    C-----C
     \   /
      NH2

• i) Toluene $\rightarrow$ A (Benzyl chloride)

  • Reagent: $\text{Cl}_2$ (chlorine gas)
  • Conditions: UV light (or heat)

• ii) A (Benzyl chloride) $\rightarrow$ B (Benzyl alcohol)

  • Reagent: Aqueous $\text{KOH}$ (potassium hydroxide) or aqueous $\text{NaOH}$ (sodium hydroxide)
  • Conditions: Heating (reflux)

• iii) Toluene $\rightarrow$ C (Nitrotoluene)

  • Reagent: Concentrated $\text{HNO}_3$ (nitric acid) and concentrated $\text{H}_2\text{SO}_4$ (sulfuric acid)
  • Conditions: 50-60°C (or room temperature)

• iv) C (Nitrotoluene) $\rightarrow$ E (Aminotoluene)

  • Reagent: $\text{Sn}$ (tin) or $\text{Fe}$ (iron) with concentrated $\text{HCl}$ (hydrochloric acid)
  • Conditions: Heating (reflux)

• v) Toluene $\rightarrow$ F (Benzoic acid)

  • Reagent: Acidified $\text{KMnO}_4$ (potassium permanganate)
  • Conditions: Heating (reflux)