Chem 3BL, Fall 2016

Dr. Pete Marsden

Augmented Pre-lab Azo Dyes

1. Write an arrow pushing mechanism for the reaction below.

2. Would the wavelength of maximum absorption of the product be larger or smaller

than that of either of the starting materials? Explain.
3. Based on the functional groups of the fabrics and the general structure of the azo
dyes, predict what types of interactions will lead to the strongest and most
intense transfer of dye molecules onto the cloth.
4. Purpose of the lab.
5. Reaction Grid (Table 1 in the experimental procedure document).
a. Recreate the grid in your notebook.
b. Determine the amount of each starting material that corresponds to 1.4
mmol.
c. Determine the MW of each possible product (A through L) based on the
reactions occurring throughout the lab (diazotization followed by EAS.
Think of how many hydrogen atoms are lost and nitrogen atoms are
added).
d. Calculate a theoretical yield for each of the possible dyes, A through L, in
millimoles and grams.
6. Clear procedure with a numbered list of steps.
a. Make sure to calculate the milligrams of NaNO2 you will be adding.
b. Calculate the number of millimoles of Na2CO3 you are adding.
c. Calculate the number of millimoles of HCl you are adding.
d. Make careful note of when to keep solutions cold, and when to warm
them.
e. Calculate the number of millimoles of NaOH you are adding.
f. Leave room for general observations throughout the experiment, as well
as space for the specific observations and pieces of data described in the
procedure.
7. Clean-up protocol.