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NEET CHEMISTRYMedium

In a set of the given reactions, acetic acid yielded a product C: CH3COOH+PCl5AAnh.AlCl3C6H6BetherC2H5MgBrCCH_3COOH + PCl_5 \rightarrow A \xrightarrow[Anh. AlCl_3]{C_6H_6} B \xrightarrow[ether]{C_2H_5MgBr} C Product C would be:

A

CH3CH(OH)C2H5

B

CH3COC6H5

C

CH3CH(OH)C6H5

D

CH3C(OH)(C6H5)C2H5

Step-by-Step Solution

The reaction sequence proceeds as follows:

  1. Formation of A: Acetic acid (CH3COOHCH_3COOH) reacts with phosphorus pentachloride (PCl5PCl_5) to form acetyl chloride (CH3COClCH_3COCl). This is a standard method for preparing acyl chlorides. CH3COOH+PCl5CH3COCl+POCl3+HClCH_3COOH + PCl_5 \rightarrow CH_3COCl + POCl_3 + HCl
  2. Formation of B: Acetyl chloride (A) reacts with benzene (C6H6C_6H_6) in the presence of anhydrous aluminium chloride (AlCl3AlCl_3) to form acetophenone (C6H5COCH3C_6H_5COCH_3). This is the Friedel-Crafts Acylation reaction. CH3COCl+C6H6AlCl3C6H5COCH3CH_3COCl + C_6H_6 \xrightarrow{AlCl_3} C_6H_5COCH_3
  3. Formation of C: Acetophenone (B), a ketone, reacts with ethyl magnesium bromide (C2H5MgBrC_2H_5MgBr, a Grignard reagent) followed by hydrolysis to form a tertiary alcohol. The alkyl group from the Grignard reagent adds to the carbonyl carbon. C6H5COCH3+C2H5MgBretherC6H5C(OMgBr)(CH3)C2H5H3O+C6H5C(OH)(CH3)C2H5C_6H_5COCH_3 + C_2H_5MgBr \xrightarrow{ether} C_6H_5-C(OMgBr)(CH_3)-C_2H_5 \xrightarrow{H_3O^+} C_6H_5-C(OH)(CH_3)-C_2H_5

The final product C is 2-phenylbutan-2-ol.

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