Question

Introduction One of the best ways to make aromatic amines is to exploit a rearrangement reaction that breaks a C-C bond. To achieve the rearrangement, you need to make an acyl nitrene intermediate (or suitable derivative). There are a variety of these processes: the Curtius and Schmidt rearrangements access the nitrenes from acyl azides, but these can be explosive, so aren't ideal for an undergraduate lab. The other method is to use the Hofmann rearrangement (Solomons p 907-908), which uses an amide as starting material. This requires an oxidizing agent, usually bromine, but can be effectively performed using household bleach in basic solution. In this experiment, you will synthesize 3-nitroaniline via a mild Hofmann rearrangement with bleach. NaOCI (5%) O NUNH2 NaOH isocyanate intermediate Figure 1. Reaction Scheme. Prelab Report (12 pts) Objectives (2 pts): Describe the central objectives of this experiment. Describe one learning outcome you expect to have gained at the end of this experiment. Procedure (3 pts): In your prelab report, write an outline of the experimental procedure. Remember to include your name, lab section and the name of your TA (on each page), and the title and number of the experiment. Chemical Table (4 pts): 1) Fill in the reaction table below. Make sure you correctly calculate the molar amounts of your reactants. name formula mol.-eq. My mmol amount 3-nitrobenzamide 1.0 g 9.0 mL 5.75% Bleach (aq.) 1 M Aqueous NaOH 12 mL product 2) Calculate the Theoretical Yield of your product, i.e. the mass you would expect to recover (assuming 100% conversion to product).

If you could answer 1 and 2 please. Thanks!

Answer 1

NO2 CO Nooh mw Benzemidel HV Neme formula mol. mmol amount 13-nitro, HAN I T 166.13 16.019 1.o sim 575% Bleach Naocl11.10 74.44 16.66 19.om) fm.agwool Noot 2.0 40 12.818 18ml 1 Product 1672 1 138.14 16.019 10.83) gm 0 from 1.0gm of ③ =) 0.837 sm of 6 will form. Amount of (B) = 138.14x10gm=0.831 gmit 166.13