Organic Chemistry lab witting reaction !\' : 11 Emphasis THeading 11 Normal! Str

Question

Organic Chemistry lab witting reaction !' : 11 Emphasis THeading 11 Normal! Strong Subtitle Paragraph 1. If you were to assume a 95% yield for the formation of the phosphonium ion, how many milligrams of benzyl chloride and triphenyl phosphine would you need to prepare 220 mg of benzyltriphenylphosphonium chloride? 2 In your own words, expl ain why only the Eitrans form of the 9-0 phenylethenyDanthracene in this reaction? 3. What color(G) did you observe an the second part of the experiment? It was an example of what phenomenon? Why is light emitted from this reaction?

Explanation / Answer

1. molecular wt of benzyltriphenylphosphonium chloride = 388.86 gm therefore, 220 mg = 0.22g / 388.86 = 0.000566gm =0.56mg

2. Because the isomer that is formed is decided by the stability of the ylide of intermediate. In this reaction, the ylide is stabilized via resonance, which causes itto preferentially form the E/trans isomer

3.  Vblue color will be observed during the reaction. This was an example of chemiluminecsence. The light was emitted because the fluctuation from excited state tonon-excited state. Through this fluctuation, light is emitted.

4. The purpose of the NaOH is to deprotonate to form the ylide for the witting reaction.

5.

a) benzyl chloride, triphenylphosphine and benzaldehyde

b) benzyl chloride, triphenylphosphine, and 2-propanone

c) 9-(cholromethyl)anthracene, triphenylphosphine, and 9-anthraldehyde

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