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NEET CHEMISTRYAldehydes, Ketones and Carboxylic AcidsMedium

Question

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.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Aldehydes, Ketones and Carboxylic Acids. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAldehydes, Ketones and Carboxylic Acidsreactionsaceticyieldedproductchcooh

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