Ouellette 2/e Ch 10.
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The questions here are all about C5H10O. There are many isomers with this formula. (This quiz makes use of information from all your organic chemistry material, especially Ouellette 2/e Ch 4, 8, 9, 10. If you are using another book, these are the chapters on alkenes, alcohols, ethers and simple carbonyl compounds.)
These questions are all open-ended. There are many possible answers. I encourage you to turn in your efforts, and I will look at them.
Be sure to explain your answers; the explanation is really the whole point.
1. In each part, draw one isomer with the requested structural feature(s).
a. a primary alcohol
2. Compare your compounds in parts a, d, e, f, above. Which one of them would probably have the highest boiling point? Why?
You should be able to answer this question even if you do not have structures for all the relevant parts of #1. Why?
3. You now test a compound to see what it is. In each part, you are given some results. Draw and name a compound that fits the data. Explain what each test tells you. (The parts are independent; that is, each part deals with a different compound. More than one compound may fit the data.)
Some of the reactions are from the text. Some are introduced in the notes above.
a. Reacts with sodium, not with potassium permanganate.
b. Reacts with KMnO4, but not with Na.
c. Reacts with H2/Pt, and with sodium.
d. Reacts with H2/Pt, not with chromic acid.
e. Does not react with any of the following: H2/Pt, Na, DNPH. (After you find such a compound... What would you expect it to react with?)
This quiz is based on an article by Robert Perkins (Kwantlen College, Surrey, BC, Canada), "Which Organic Molecule Should I Pick", Journal of Chemical Education 72:124, Feb 95.
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Last update: August 16, 2011