15. Analytical Techniques:IR, NMR, Mass Spect
Mass Spect:Fragmentation
32PRACTICE PROBLEM
A scientist mixed 4-phenylbutanoic acid with concentrated sulfuric acid while maintaining the temperature at 170°C. After a few minutes, the reaction mixture was poured into water. The product was extracted from this solution using dichloromethane. The extraction solvent was then evaporated leaving behind a good amount of the product. The mass spectrum of this product shows a molecular ion peak at m/z 146 and its IR spectrum shows a prominent stretch at 1710 cm−1 while the carboxylic stretch was missing. The 1H NMR spectrum of this product is shown below. What is the product?
![](https://lightcat-files.s3.amazonaws.com/problem_images/e28d0a2666bd2f60-1675267056015.jpg)
![](https://lightcat-files.s3.amazonaws.com/problem_images/a71dfcfa9aaff9db-1675267391316.jpg)
A scientist mixed 4-phenylbutanoic acid with concentrated sulfuric acid while maintaining the temperature at 170°C. After a few minutes, the reaction mixture was poured into water. The product was extracted from this solution using dichloromethane. The extraction solvent was then evaporated leaving behind a good amount of the product. The mass spectrum of this product shows a molecular ion peak at m/z 146 and its IR spectrum shows a prominent stretch at 1710 cm−1 while the carboxylic stretch was missing. The 1H NMR spectrum of this product is shown below. What is the product?