課程名稱︰有機化學一
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）︰2020/12/3
考試時限（分鐘）：110min
試題 :
1. Please provide structures of the following groups:
(a) methylene
(b) vinyl
(c) halohydrin
(d) bromonium
(e) methanide
2. Describe the following terms:
(a) Zaitsev’s rule
(b) Markovnikov’s rule
3. Provide a reasonable mechanism for each of the following reaction.
https://i.imgur.com/lSOwUWL.jpg
4. What is the smallest trans cycloalkane that is stable at room temperature? Gi
ve its name and draw its structure.
5. Provide a mechanism to account for the following transformation.
https://i.imgur.com/LeWGNOi.jpg
6. Predict the more stable alkene of each pair:
(a) 2-methyl-2-pentene or 2,3-dimethyl-2-butene
(b) cis-3-hexene or trans-3-hexene.
Please briefly describe how you could experimentally determine their relative st
ability.
7. What product(s) would you expect from the following solvolysis? Provide a mec
hanism to explain your answers.
https://i.imgur.com/H0ebgld.jpg
8. Rank the following in terms of decreasing nucleophilicity;
(a) CH3OH
(b) CH3CO2-
(c) CH3O-
9. Rank the following alkyl bromides in order of decreasing reactivity as a subs
trate in an SN2 reaction.
https://i.imgur.com/p8KSSbH.jpg
10. Which reaction in the following pairs would you expect to give better yield
of the desired product? Explain your answers.
https://i.imgur.com/tNYsS7t.jpg
11. Please compare the difference between basicity and nucleophilicity.
12. Would you expect the following reaction to occur faster in DMF or in EtOH? E
xplain your answers.
CH3CH2CH2Br+NaCN —> CH3CH2CH2CN+NaBr
13. Write a three-dimensional formula for the product formed when 1-methylcycloh
exene is treated with each of the following reagents. In each case, designate th
e location of deuterium or tritium atoms.
(a) I) BD3, THF II)CH3CO2H
(b) I) BH3, THF II)CH3CO2T
14.
(a) When cis-1-bromo-2-methylcyclohexane undergoes an E2 reaction, two products(
cyclohexenes) are formed. What are those two cyclohexenes, and which would you e
xpect to be the major product? Write conformational structures showing how each
is formed.
(b) When trans-1-bromo-2-methylcyclohexane reacts in an E2 reaction, only one cy
clohexenes is formed. What is this product? Write conformational structures show
ing why it is the only product.
15. What major product(s) would you expect from each of the following reactions?
https://i.imgur.com/auhPGgC.jpg
16. Provide proper conditions for the following transformations. In each case mo
re than one reaction is required and you may use any other needed reagents.
https://i.imgur.com/oFthBVJ.jpg
17. Compound A has the molecular formula
C10H16 and is known not to contain any triple bonds. When treated with excess hy
drogen and a platinum catalyst, compound A is converted to
2,6-dimethyloctane. Ozonolysis of compound A followed by treatment with Me2S yie
lds 2 mol of HCHO, 1 mol of CH3COCH3, and a third compound B with the formula C5
H6O3. Please deduce the structures of compound A and B, and explain your answers
.