Provide an example of a phase-transfer catalyst other than the ...

[biggirl4568]

Provide an example of a phase-transfer catalyst other than the one used in this experiment.

Question 2

Identify each of the following reactions as an oxidative addition or reductive elimination.
 
Question 3

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Question 4

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Question 5

Based on your background reading about the Wittig reaction, propose a synthesis of the phosphorane used in this experiment, starting with triphenylphosphine and whatever other commercially available reactants and reagents you choose.

Question 6

The Horner-Wadsworth-Emmons reaction is a commonly used variant of the Wittig reaction. What feature of this reaction, shown below, is particularly useful compared with the Wittig reaction? Hint: Consider the structure of the product(s).
 

Question 7

A researcher used column chromatography to separate two compounds. The desired compound, which was quite valuable, had an Rf approximately equal to 0.5. Two-mL fractions were collected, giving the TLC results shown below. Based on these results, explain what the researcher needs to do to maximize recovery of the desired compound, including the use of additional separations.

[katara]

Answer to Question 1

Tetraoctylammonium bromide is just one of many possibilities.

Answer to Question 2



Answer to Question 3



Answer to Question 4

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Answer to Question 5

One example is shown below.

Answer to Question 6

The phosphorus-containing product is water soluble, allowing for the separation of the alkene from the reaction mixture by a simple aqueous extraction.

Answer to Question 7



Answer to Question 8

First combine fractions 6-10 and then evaporate off the solvent to isolate the compound. Combine fractions 3-5, evaporate off the solvent and add this mixture to a new column. In addition, one could collect smaller fractions or use a more non-polar solvent system to more effectively separate these two compounds.

Answer to Question 9

If product were dissolved in the eluent when elution began, it would result in the continuous addition of product to the column throughout the separation. This would lead to little or no separation of the product(s).