High School

Write the overall balanced equation and mechanism for the transformation of bromobenzene into benzoic acid through a Grignard reaction. Include all reagents and products but not solvents.

Answer :

The overall balanced equation for the transformation of bromobenzene into benzoic acid through a grignard reaction is C6H5Br + Mg + CO2 + HCl → C6H5COOH + MgBrCl.

To transform bromobenzene into benzoic acid through a Grignard reaction, follow these steps:

Step 1: Formation of phenylmagnesium bromide (Grignard reagent)

Bromobenzene (C6H5Br) reacts with magnesium (Mg) in the presence of ether (dry Et2O) to form phenylmagnesium bromide (C6H5MgBr).

C6H5Br + Mg → C6H5MgBr

Step 2: Reaction with carbon dioxide (CO2)

Phenylmagnesium bromide (C6H5MgBr) reacts with carbon dioxide (CO2) to form magnesium salt of benzoic acid (C6H5COOMgBr).

C6H5MgBr + CO2 → C6H5COOMgBr

Step 3: Acidification

The magnesium salt of benzoic acid (C6H5COOMgBr) is treated with a dilute acid, like hydrochloric acid (HCl), to form benzoic acid (C6H5COOH) and a magnesium salt (MgBrCl).

C6H5COOMgBr + HCl → C6H5COOH + MgBrCl

Using Grignard reaction, the overall balanced equation for the transformation of bromobenzene into benzoic acid is:

C6H5Br + Mg + CO2 + HCl → C6H5COOH + MgBrCl

Mechanism:

1. Single-electron transfer from magnesium to bromobenzene forms a radical anion, which then reacts with magnesium to form phenylmagnesium bromide.

2. Nucleophilic attack of the phenyl group on carbon dioxide, followed by bond rearrangement, results in the formation of the magnesium salt of benzoic acid.

3. Acidification of the magnesium salt generates benzoic acid and a magnesium salt.

Learn more about Grignard reaction:

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