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Question #44007
The Question
Consider the following synthetic sequence starting from methyl 4-aminobenzoate:
Identify the major product .
Options
- A.
Methyl 4-(hydroxy(phenyl)methyl)benzoate
- B.
4-(hydroxy(phenyl)methyl)benzoic acid
- C.
Polymeric mixture of tertiary alcohols and ketones
- D.
Methyl 4-benzoylbenzoate
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Mechanism_Trap
Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.
Concepts Behind This Question
Grignard Reaction Pathways|Sandmeyer vs Gattermann|Diazotization Temperature Sensitivity
Why This Question Is Tricky
Common Mistakes
This problem tests the student's ability to recognize functional group incompatibility during organometallic synthesis.
While the sequence of Diazotization, Sandmeyer, and Grignard addition appears straightforward, students often fall into the trap of assuming the Grignard reagent () will wait peacefully for the addition of the external electrophile (benzaldehyde).
The 'Chemical Exception' here is that Grignard reagents cannot be generated in the presence of reactive electrophilic centers (like esters, ketones, or amides) on the same molecule.
The hidden mechanism is the rapid intermolecular nucleophilic acyl substitution (self-condensation) that consumes the Grignard reagent immediately upon formation, leading to polymerization rather than the desired cross-coupled product.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Aldehydes, Ketones, and Carboxylic Acids - Class 12 |
| Concept | Grignard Reaction Pathways |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |