Sulfanilamide Synthesis Report Guidelines:
Note: These are general guidelines, the sentence lengths do NOT have to match those listed; they are simply used for a guide for you. Focus more on the content of your sections than length; did you actually understand the science behind the reaction and convey that information concisely?
Abstract/Purpose (4-6 sentences) State the general goal in a few words and/or structures. Mention briefly the results and conclusion of the synthesis. Introduction/Theory (20-24 sentences) This should cover the chemistry behind the chemical reactions and experimental techniques (how and why the experiment/technique works). Include the reactions using structures and the complete mechanisms. The mechanism will be graded for completeness and accuracy.
The mechanism must be done electronically or NEATLY by hand. If we cannot read/interpret part of your mechanism due to sloppiness, we will assume that part of the mechanism is wrong.
• You do NOT need to show the mechanism for the reduction of nitrobenzene with zinc.
• You ARE responsible for all other mechanisms.
In this section you may explain the regio- or stereoselectivity of a reaction, why some reactions are air and/or moisture sensitive, the importance of protecting groups or significance of LeChatlier’s principle. If you perform a recrystallization or a reflux you may explain briefly the science behind this purification technique.
• Include a brief discussion on the background of sulfanilamide and sulfa drugs.
• Week 1 specifics: o Reduction of nitrobenzene to aniline
¦ Briefly describe the role of zinc.
¦ Explain the theory behind monitoring this reaction based on water solubility.
¦ Describe why it was so important to reach a pH of 13 or higher by addition of conc. NaOH. What was a potential consequence of stopping at a pH of less than 13.
o Synthesis of acetanilide from aniline:
¦ Describe briefly the role of acetic anhydride. For example, what kind of reaction took place between the anhydride and the aniline?
¦ Why was it so important to be sure that the acetanilide product had a chance to dry completely before taking it on in the next step?
• Week 2 specifics: o Formation of the sulfonyl chloride from acetanilide by reaction with chlorosulfonic acid
¦ Describe briefly the role of chlorosulfonic acid
¦ Be sure to address the fact that this reagent had two different jobs. Discuss why it was so important to control the temperature carefully. What was the potential consequence of allowing the reaction mixture to heat up too much during the beginning part of the reaction?
¦ Why was it so important to take the sulfonyl chloride on immediately after it was formed? What was the possible consequence of allowing the product to be exposed to water for too long?