JEE Main · 2022 · Shift-IImediumHALO-082

In the given reaction, 'A' can be:

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

In the given reaction, image 'A' can be:

Options
  1. a

    Benzyl bromide

  2. b

    Bromobenzene

  3. c

    Cyclohexyl bromide

  4. d

    Methyl bromide

Correct Answerb

Bromobenzene

Detailed Solution

Step 1: Analyze the product

Product structure shows triphenylmethanol: \ce(C6H5)3COH\ce{(C6H5)3C-OH}

This has:

  • Three phenyl groups
  • One OH group
  • Central carbon

Step 2: Understand Grignard reaction with esters

Grignard + Ester → Tertiary alcohol (2 equiv of Grignard)

General reaction: \ce2RMgX+RCOOR>R2RCOH\ce{2 R-MgX + R'-COOR'' -> R2R'C-OH}

For methyl benzoate (\ceC6H5COOCH3\ce{C6H5-COOCH3}): \ce2RMgX+C6H5COOCH3>R2(C6H5)COH\ce{2 R-MgX + C6H5-COOCH3 -> R2(C6H5)C-OH}

Step 3: Determine R group

Product: \ce(C6H5)3COH\ce{(C6H5)3C-OH}

This means:

  • R = \ceC6H5\ce{C6H5} (phenyl)
  • R' = \ceC6H5\ce{C6H5} (from ester)

So: \ce2C6H5MgX+C6H5COOCH3>(C6H5)3COH\ce{2 C6H5-MgX + C6H5-COOCH3 -> (C6H5)3C-OH}

Step 4: Identify compound A

Grignard reagent: \ceC6H5MgX\ce{C6H5-MgX}

Starting halide: \ceC6H5X\ce{C6H5-X} = Bromobenzene (\ceC6H5Br\ce{C6H5Br})

Answer: (b) Bromobenzene

Key Reaction Mechanism:

  1. Grignard formation: \ceC6H5Br+Mg>[THF]C6H5MgBr\ce{C6H5Br + Mg ->[THF] C6H5MgBr}

  2. First addition: \ceC6H5MgBr+C6H5COOCH3>C6H5C(=O)C6H5+CH3OMgBr\ce{C6H5MgBr + C6H5-COOCH3 -> C6H5-C(=O)-C6H5 + CH3OMgBr} (Ketone intermediate)

  3. Second addition: \ceC6H5MgBr+C6H5C(=O)C6H5>(C6H5)2C(OMgBr)C6H5\ce{C6H5MgBr + C6H5-C(=O)-C6H5 -> (C6H5)2C(OMgBr)-C6H5}

  4. Hydrolysis: \ce(C6H5)3COMgBr+H3O+>(C6H5)3COH\ce{(C6H5)3C-OMgBr + H3O+ -> (C6H5)3C-OH}

Key Points:

  • Esters react with 2 equiv of Grignard → tertiary alcohol
  • Aldehydes/ketones react with 1 equiv → secondary/tertiary alcohol
  • Aryl Grignards can be formed from aryl bromides

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