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Question #44921
The Question
An industrial synthesis of a specialized azo dye requires the preparation of benzenediazonium chloride from -phenylacetamide.
Step 1: of -phenylacetamide undergoes complete nucleophilic acyl substitution (hydrolysis) in aqueous at . The resulting aqueous mixture has a total heat capacity .
Step 2: To shift the basicity-solvation competition and accelerate nitrosation, of -dimethylformamide (DMF, specific heat capacity ) initially at is added to the hot mixture.
Step 3: The aprotic nature of DMF deprives the diazonium cation of hydrogen-bond stabilization, drastically lowering the activation barrier for loss. To prevent decomposition, the mixture is cooled to exactly by adding solid ice (at ).
Step 4: of is added, and diazotization () goes to completion at .
Assuming no heat exchange with the surroundings and that the melted ice remains at , calculate the total mass of ice required to achieve the cooling and maintain the system strictly at during the entire process.
(Given: of ice = , Molar mass of = )
Options
- A.
750 g
- B.
600 g
- C.
690 g
- D.
975 g
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Numerical_Precision
Improve calculation stamina and avoid rounding errors in high-stakes competitive examinations.
Concepts Behind This Question
Diazotization Temperature Sensitivity|Basicity-Solvation Competition|Nucleophilic Acyl Substitution
Why This Question Is Tricky
Common Mistakes
This problem tests the physical chemistry underlying the rote-memorized '0-5 °C' rule for diazotization.
Students often overlook that diazotization is highly exothermic and that the stability of the diazonium intermediate is heavily solvent-dependent.
By introducing an aprotic polar solvent (DMF), the 'Basicity-Solvation' balance shifts: the diazonium cation loses critical hydrogen-bond stabilization, lowering the activation energy for loss and making strict thermodynamic control mandatory.
The student must synthesize concepts from nucleophilic acyl substitution (hydrolysis of acetanilide to aniline), thermochemistry (sensible heat and latent heat), and reaction stoichiometry to calculate the exact cooling capacity required to prevent thermal decomposition.
Common traps include forgetting the exothermic heat of reaction (yielding 600 g) or neglecting the cooling of the added solvent (yielding 690 g).
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Amines - Class 12 |
| Concept | Diazotization Temperature Sensitivity |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |