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Aldehydes Ketones and Carboxylic Acids question

2022 · 26 Jun · Shift 2 · Q8
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Aldehydes Ketones and Carboxylic Acids question

2022 · 26 Jun · Shift 2 · Q8

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Oxidation of toluene to benzaldehyde can be easily carried out with which of the following reagents?
  1. A
    CrO3CrO_3CrO3​/acetic acid, H3O+H_3O^+H3​O+
  2. B
    CrO3CrO_3CrO3​/acetic anhydride, H3O+H_3O^+H3​O+
  3. C
    KMnO4KMnO_4KMnO4​/HClHClHCl, H3O+H_3O^+H3​O+
  4. D
    COCOCO/HClHClHCl, anhydrous AlCl3AlCl_3AlCl3​
View written solutionFree

Correct answer: B

  1. Identify the transformation

We need to convert toluene 4benzyl methyl group4 into benzaldehyde:

C6H5CH3⟶C6H5CHOC_6H_5CH_3 \longrightarrow C_6H_5CHOC6​H5​CH3​⟶C6​H5​CHO

This is controlled side-chain oxidation of an alkylbenzene.


  1. Check each reagent

Option A: CrO3CrO_3CrO3​/acetic acid, H3O+H_3O^+H3​O+

This is a strong oxidizing system. Such reagents generally oxidize the benzylic side chain further, not stopping cleanly at the aldehyde stage. The product tends toward benzoic acid rather than benzaldehyde.

So, A is not suitable.


Option B: CrO3CrO_3CrO3​/acetic anhydride, H3O+H_3O^+H3​O+

This is the Etard-type controlled oxidation condition used for converting toluene to benzaldehyde. In acetic anhydride, overoxidation is suppressed, and after hydrolysis:

C6H5CH3→H3O+CrO3/(CH3CO)2OC6H5CHOC_6H_5CH_3 \xrightarrow[H_3O^+]{CrO_3/(CH_3CO)_2O} C_6H_5CHOC6​H5​CH3​CrO3​/(CH3​CO)2​OH3​O+​C6​H5​CHO

So, B is correct.


Option C: KMnO4KMnO_4KMnO4​/HClHClHCl, H3O+H_3O^+H3​O+

KMnO4KMnO_4KMnO4​ is a very strong oxidizing agent for benzylic side chains. Toluene is oxidized completely to benzoic acid:

C6H5CH3→KMnO4C6H5COOHC_6H_5CH_3 \xrightarrow{KMnO_4} C_6H_5COOHC6​H5​CH3​KMnO4​​C6​H5​COOH

Hence, C is incorrect.


Option D: COCOCO/HClHClHCl, anhydrous AlCl3AlCl_3AlCl3​

This is the GattermannKoch formylation reagent. It introduces a formyl group directly onto benzene rings by electrophilic substitution. It is used for:

C6H6→C6H5CHOC_6H_6 \rightarrow C_6H_5CHOC6​H6​→C6​H5​CHO

It is not oxidation of toluene to benzaldehyde.

So, D is incorrect.


  1. Conclusion

The reagent that easily oxidizes toluene to benzaldehyde is:

B: CrO3/acetic anhydride, H3O+\boxed{\text{B: } CrO_3/\text{acetic anhydride},\ H_3O^+}B: CrO3​/acetic anhydride, H3​O+​

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