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What would be the theoretical yield? Experiment 9: SN2 substitution: Synthesis o

ID: 556358 • Letter: W

Question

What would be the theoretical yield?

Experiment 9: SN2 substitution: Synthesis of Virstatin ethyl ester THIS EXPERIMENT REQUIRES BALANCED CHEMICAL EQUATIONS AND THEORETICAL YIELD CALCULATION N THE PRE- AND POST-LABS (hint: the equation below is not balanced Hurt K-CO3. DMF 1h REQUIRED READING Chapter 7: Setting up organic reactions, section 7.3, page 90 Chapter 9: Filtration, section 9.2, page 134 pter 15: Recrystallization, page 221 (pay attention to insoluble impurities sections) Chapter 21: Infrared spectroscopy, page 311 (lab spectrometers have an ATR attachment) ECOMMENDED KLEIN READING Chapter 7: Substitution reactions, page 287 INTRODUCTION Cholera is a terrible disease, endemic in much of Africa, and the cause of many millions of deaths in historic times. It is a water-borne disease, the result of poor sanitation and sanitary practices. E food and drinking water infected with the gram-negative bacterium Vibrio cholera is the primary mean f transmission. No other common disease kills as quickly. Upon infection, death can occur in as little as three hours in severe cases. More commonly, from the onset of exhaustive diarrhea to shock can take 4 to 12 hours, with death in 18 hours to several days when untreated. Loss of fluids can be at the rate of one liter per hour The most effective treatment for cholera is by oral rehydration to replace the loss of electrolytes; antibiotics merely shorten the course of the disease. Cholera can be prevented by municipal water treatment and the construction of proper water supplies, and so is no longer a health threat in fully developed countries water and problem with modern antibiotics is the development of mutations in the bacteria being treated nfers resistance to their action. The most notorious is methicillin resistant Staphylococcus aureus A major MRSA). Staph bacteria developed resistance to penicillin in 1947, just four years after it was introduced It is very common in hospitals, and staph is now resistant to a broad spectrum of antibiotics. Platensimycin is one of the antibiotics produced biosynthesis which gram-positive bacteria need to by Streptomyces platensis, and it blocks fatty acid synthesize their cell membrane. It has been shown effec ctive against MRSA in mice. Cholera has developed a similar resistance to antibiotics, so another avenue for stopping the reproduction of the bacterium was explored. Virstatin is not an antibiotic; it is a small molecule inhibitor. It does not kill the V. cholera bac instead decreases its virulence. It inhibits the genes that promote colonies of the bacteria to f terium, but 29 I P a g e

Explanation / Answer

Virstatin Ethyl Ester-Yield:The experimental yield of the final solid (tan needles) was 0.2775g.

The theoretical yield of virstatin ethylester was 0.400g therefore the reaction had a percent yield of 69%.

Melting point:The literature melting point for Virstatin Ethyl Ester is recorded as 90 degrees Celsius. The experimental melting point collected for Virstatin Ethyl Ester was actually 91.8-93.1

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