Toluene is nitrated and the resulting product is reduced with tin and hydrochloric acid. The product so obtained is diazotised and then heated with cuprous bromide. The reaction mixture so formed contains

Options

A. mixture of o- and m-bromotoluene
B. mixture of o- and p-bromoaniline
C. mixture of o- and p-dibromobenzene
D. mixture of o- and p-bromo anilines

Explanation

To solve the problem step by step, we will follow the reactions of toluene as described in the question.

### Step 1: Nitration of Toluene
Toluene (C₆H₅CH₃) undergoes nitration when treated with concentrated nitric acid (HNO₃) and sulfuric acid (H₂SO₄). The electrophile generated in this reaction is the nitronium ion (NO₂⁺). Due to the presence of the electron-donating methyl group (-CH₃), the nitro group can be introduced at the ortho and para positions relative to the methyl group.

**Products:**
- Ortho-nitrotoluene (C₆H₄(NO₂)(CH₃))
- Para-nitrotoluene (C₆H₄(NO₂)(CH₃))

### Step 2: Reduction of Nitro Group
The nitro groups in both ortho and para nitrotoluene can be reduced to amino groups (-NH₂) using tin (Sn) and hydrochloric acid (HCl). This process is known as the Clemmensen reduction.

**Products:**
- Ortho-toluidine (C₆H₄(NH₂)(CH₃))
- Para-toluidine (C₆H₄(NH₂)(CH₃))

### Step 3: Diazotization
Next, the amino groups in ortho-toluidine and para-toluidine are converted to diazonium salts by treating them with sodium nitrite (NaNO₂) and hydrochloric acid (HCl). This process is known as diazotization.

**Products:**
- Ortho-diazotoluene (C₆H₄(N₂⁺)(CH₃)Cl⁻)
- Para-diazotoluene (C₆H₄(N₂⁺)(CH₃)Cl⁻)

### Step 4: Reaction with Cuprous Bromide
Finally, the diazonium salts are treated with cuprous bromide (CuBr) to perform Sandmeyer’s reaction. In this reaction, the diazonium group (N₂⁺) is replaced by a bromine atom (Br).

**Products:**
- Ortho-bromotoluene (C₆H₄(Br)(CH₃))
- Para-bromotoluene (C₆H₄(Br)(CH₃))

### Final Answer
The reaction mixture contains a mixture of ortho-bromotoluene and para-bromotoluene.

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