課程名稱︰有機化學二
課程性質︰化學系大二必修
課程教師︰羅禮強
開課學院：理學院
開課系所︰化學系
考試日期（年月日）︰2021/4/8
考試時限（分鐘）：110min
試題 :
1. Please name the following groups/compounds
(a) CF3SO2O-
(b) PhMgBr
(c) SOCl2
(d) and (e):
https://i.imgur.com/7SaUIpi.jpg
2. Which is the best combination to prepare ethoxycyclopentane via the Williamso
n method?
3. Draw the structures of all the products formed when 1-methylcyclopentene is s
ubjected to the hydroboration-oxidation sequence.
4. Apply the polygon-and-circle method to the following cyclopropenyl ions shown
below, construct their MOs and whether they would be aromatic or not.
https://i.imgur.com/t9ayQiH.jpg
5. Show how you might carry out the following transformations. More than one ste
p may be required. You can use benzene and any other reagents with two or fewer
carbons.
https://i.imgur.com/JqjI95u.jpg
6. The Lewis structure of both pyridine and pyrrole have an electron pair on the
nitrogen atom, suggesting that both substances might posses basic properties. H
owever, only pyridine reacts readily with HCl to form pyridinium chloride, while
pyrrole is rather unreactive. Explain clearly, using relative diagrams to illus
trate/clarify your answer.
https://i.imgur.com/6r7wEWr.jpg
7. Provide a mechanism to account for the following reaction.
https://i.imgur.com/b8SHy9g.jpg
8. Predict the major organic product from each of the following reactions.
https://i.imgur.com/xw2ZBC3.jpg
9. Provide a mechanism to account for the following reactions.
https://i.imgur.com/Y4NjdIf.jpg
10. Azulene has an appreciable dipole moment. Write resonance structures for azu
lene that explain this dipole moment and that helps explain is aromaticity.
https://i.imgur.com/AqWYk1I.jpg
11. Please rationalize why the chemical shift of carbon (a) of the following com
pound appears more downfield than that of carbon (b) in the C-13 NMR spectrum.
https://i.imgur.com/rZ8ZYeD.jpg