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Aldehydes Ketones and Carboxylic Acids question

2017 · Shift 1 · Q2
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Aldehydes Ketones and Carboxylic Acids question

2017 · Shift 1 · Q2

JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMCQ+3 / −1
Columns 1, 2 and 3 contain starting materials, reaction conditions, and type of reactions, respectively.

Column 1 Column 2 Column 3
(I) Toluene (i) NaOHNaOHNaOH/Br2 (P) Condensation
(II) Acetophenone (ii) Br2/hv (Q) Carboxylation
(III) Benzaldehyde (iii) (CH3CO)2O/
CH3COOK
(R) Substitution
(IV) Phenol (iv) NaOHNaOHNaOH/CO2 (S) Haloform
For the synthesis of benzoic acid, the only CORRECT combination is
  1. A
    (II) (i) (S)
  2. B
    (IV) (ii) (P)
  3. C
    (I) (iv) (Q)
  4. D
    (III) (iv) (R)
View written solutionFree

Correct answer: A

The user wants me to identify the correct combination of starting material, reaction conditions, and reaction type for the synthesis of benzoic acid.

I will analyze each option step-by-step:

Option A: (II) (i) (S)

  1. Starting Material (II): Acetophenone (C6H5COCH3C_6H_5COCH_3C6​H5​COCH3​). This is a methyl ketone attached to a phenyl group.
  2. Reaction Conditions (i): NaOH/Br2NaOH/Br_2NaOH/Br2​. These are the reagents for the haloform reaction.
  3. Reaction Type (S): Haloform reaction.
  4. Analysis: Methyl ketones undergo the haloform reaction. Acetophenone reacts with bromine in the presence of sodium hydroxide to form sodium benzoate and bromoform (CHBr3CHBr_3CHBr3​). The reaction is: C6H5COCH3+3Br2+4NaOH→C6H5COONa+CHBr3+3NaBr+3H2OC_6H_5COCH_3 + 3Br_2 + 4NaOH \rightarrow C_6H_5COONa + CHBr_3 + 3NaBr + 3H_2OC6​H5​COCH3​+3Br2​+4NaOH→C6​H5​COONa+CHBr3​+3NaBr+3H2​O The resulting sodium benzoate (C6H5COONaC_6H_5COONaC6​H5​COONa) can be easily converted to benzoic acid by acidification (e.g., adding HCl). C6H5COONa+H+→C6H5COOH+Na+C_6H_5COONa + H^+ \rightarrow C_6H_5COOH + Na^+C6​H5​COONa+H+→C6​H5​COOH+Na+
  5. Conclusion: This combination correctly describes a synthesis of benzoic acid. The starting material, reagents, and reaction type are all consistent.

Option B: (IV) (ii) (P)

  1. Starting Material (IV): Phenol (C6H5OHC_6H_5OHC6​H5​OH).
  2. Reaction Conditions (ii): Br2/hνBr_2/h\nuBr2​/hν. These conditions are for free radical halogenation, typically at an allylic or benzylic position. Phenol does not have such a position.
  3. Reaction Type (P): Condensation. This reaction is not a condensation reaction. Also, it does not produce benzoic acid.
  4. Conclusion: This combination is incorrect.

Option C: (I) (iv) (Q)

  1. Starting Material (I): Toluene (C6H5CH3C_6H_5CH_3C6​H5​CH3​).
  2. Reaction Conditions (iv): NaOH/CO2NaOH/CO_2NaOH/CO2​. These are the conditions for the Kolbe-Schmitt reaction, which is used to carboxylate phenols (e.g., converting phenol to salicylic acid). Toluene does not react under these conditions to form benzoic acid.
  3. Reaction Type (Q): Carboxylation. While the process of forming benzoic acid from toluene involves adding a carboxyl group, these specific reagents are incorrect.
  4. Conclusion: This combination is incorrect.

Option D: (III) (iv) (R)

  1. Starting Material (III): Benzaldehyde (C6H5CHOC_6H_5CHOC6​H5​CHO).
  2. Reaction Conditions (iv): NaOH/CO2NaOH/CO_2NaOH/CO2​. Benzaldehyde does not typically react with these reagents to form benzoic acid. With concentrated NaOHNaOHNaOH alone, it undergoes the Cannizzaro reaction (a disproportionation). The conversion of benzaldehyde to benzoic acid is an oxidation, not a substitution.
  3. Reaction Type (R): Substitution. This is incorrect. The conversion is an oxidation.
  4. Conclusion: This combination is incorrect.

Based on the analysis, only option A correctly describes a method for the synthesis of benzoic acid. The haloform reaction of acetophenone is a standard laboratory method for this purpose.

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