Stereoselective Wittig Reaction Lab Report

Organic Synthesis Experimental Activity: Stereoselective Wittig Reaction

Watch the following videos from the Second Semester Organic Chemistry Lab at Eastern Kentucky University, U.S.

  1. Provide the chemical reaction of the Stereoselective Wittig reaction being performed in this video.
  2. The instructor in the video mentions a Wittig reaction conducted in one of his previous videos. Draw the chemical reaction here for comparison
  3. Why do you think the Wittig reaction is this video is stereoselective and the previous example was not?
  4. Why is a base not required in this video but was required in the previous video?
  5. In many Wittig reactions, during the preparation of the Wittig Reagent (Ylide), a strong base such as n-BuLi is required. Why do you think they were able to use a weaker base (K3PO4) in the previous reaction?
  6. Draw the mechanism for the Wittig reaction in this video.
  7. Write out the reaction procedure and fill in the following reaction table.

Name

MW

Amount

mmol

equivalents

MP

Concentration

CAS#

Density

Safety Info

Appearance

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

  1. Why did the instructor use a conical vial instead of a round-bottom flask for this reaction?
  2. What organic compounds are dissolved in the hexanes and what organic compounds make up the solid (not dissolved)?
  3. The instructor evaporates the hexanes using a hot plate and air. What procedure would likely be employed if this reaction were being run on larger scale?
  4. Why does the flask being cold to the touch indicate to the instructor that more hexanes must still be present in the flask?
  5. Analyze the 1H NMR of the product.

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Organic Synthesis Experimental Activity: Wolff-Kishner Reaction

Watch the following videos from the Second Semester Organic Chemistry Lab at Eastern Kentucky University, U.S.

  1. Provide the chemical reaction of the Wolff-Kishner reaction being performed in this video.
  2. This video utilized a conventional microwave to heat the reaction. Most organic reactions that must be heated utilize a reflux apparatus. Considering Le Chatelier’s Principle as it may apply to hydrazone formation, why might it be an advantage to use a microwave instead of a reflux apparatus with condenser
  3. Describe the procedural steps and fill out the following two reaction tables for each synthetic step.

Name

MW

Amount

mmol

equivalents

MP

Concentration

CAS#

Density

Safety Info

Appearance

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Name

MW

Amount

mmol

equivalents

MP

Concentration

CAS#

Density

Safety Info

Appearance

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

  1. Why did the video instructor end up performing the reaction 3 time
  2. Provide the full mechanism of the two-step reaction.
  3. Analyze the 1H NMR spectrum of the product.

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