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18 Dec 2019

1. During the extraction of trimyristin from nutmeg, two students were given different samples of nutmeg. They noticed that one sample was very fragrant with the characteristic odor of nutmeg, while the other one looked old and was not very fragrant at all. When they asked their instructor about it, she told them it would be OK to proceed with both samples. Still skeptical, they performed the experiment and compared their results. It seemed that there was not much difference: they had approximately identical quantities of the isolated product, with almost identical melting point. Explain. (2 points)

2. During the extraction of trimyristin from nutmeg, the ground nutmeg is refluxed with ether for some time and then filtered to remove the insoluble solids. After subsequent removal of most of the ether by distillation, acetone is added to the concentrated ether extract- after some time, crystals of trimyristin separate out.

a. Explain the need for “reflux” in this procedure.

b. Why is acetone added to the concentrated ether extract? Why not simply allow all the ether to evaporate and leave behind the extracted trimyristin? Explain clearly. (1 point)

c. Where do you expect the impurities to be found? Explain clearly. (1 point)

3. Predict what you would expect to observe when each of the following substances is mixed with NaI/acetone. Would you expect a difference in their relative rates of reaction? Explain. (1 point)

a. 2-chloro-4-ethylheptane

b. 3-chloro-3-ethylheptane

c. 1-bromo-5-ethylheptane

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Deanna Hettinger
Deanna HettingerLv2
31 Dec 2019

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