Chemistry 351 - Principles of Organic Chemistry II
Spring Semester 2020, Winona State University, Dr. Thomas Nalli

Expt 4 - Nitration of Methyl Benzoate

Relevant textbook readings - Mohrig - Chapter 15, Klein - Chapter 19.1, 19.4, 19.8

Procedure Reference
https://d.web.umkc.edu/drewa/Chem322L/Handouts/Lab07HandoutNitrationOfMethylBenzoate322L.pdf

Procedures

Reaction:

Carry out the procedure as described in the reference but use a 5-mL round bottom flask equipped with a reflux condenser as the reaction vessel.

Work Up and Purification

Work the reaction up using the procedure in the reference and save a small sample of the crude product for later mp determination. Recrystallize the crude from methanol/water using the method described for mixed solvent recrystallization in Mohrig on p 189.

Analysis:

Obtain 1H NMR (CDCl3) and IR (thin film) spectra of the recrystallized product. We will likely also obtain a C-13 NMR and GC-MS on one group's product.

Do mp determinations on both the crude and recrystallized products.