作者oliver1089 (鮪魚)
看板NTU-Exam
標題[試題] 100上 楊吉水 有機化學乙 第二次期中(2)
時間Mon Jan 16 21:22:21 2012
課程名稱︰有機化學
課程性質︰必帶
課程教師︰楊吉水
開課學院：工學院
開課系所︰化工系
考試日期（年月日）︰2011/12/01
考試時限（分鐘）：110
是否需發放獎勵金：是
（如未明確表示，則不予發放）
試題 :
二.Essay Questions
1.consider the following SN2 reaction:
Br
O ▼ NaCN
／ ＼／＼ ───→
DMF
(a)Complete the above equation by drawing the mechanism and the product.
(b)Assign the configuration of the chirality center in both the substrate and
product. Make sure you draw the structure and indicate the correct atom.
(c)Does this SN2 process proceed with inversion of configuration? Explain.
2.Below are two potential methods for preparing the same ether, but only one
of them is successful.
I
＼／
/\ ───→ O
＼／ ＼
MeI ───→ /\
(a)Identify the successful approach and explain why the other fails.
(b)The route that fails to give the ether may produce another product.
Identify the product and draw a plausible mechanism of its formation.
3.Propose a mechanism for each of the following transformations:
(a) ｜ ｜ (b)
／＼◢＼ H2SO4 ／＼〃＼ ／＼/_ H2SO4 ／＼／
｜ ｜ ───→ ｜ ｜ ｜ ｜ ───→ ｜ ║
＼／￥ Δ ＼／ ＼／￥ Δ ＼／＼
OH OH
(c) \/ (d)
／＼ EtOH ／＼＿ EtOH ／＼╴
｜ ───→ ｜ ｜ ｜ ║ ＼ ───→｜ |￣＼
＼ ＼〃＼ ＼／＼／ Δ ＼／
︽／
｜
OTs
4.Identify the reagents you would use to achieve each of the following
transformations in maximum steps of two. You don't have to write down any
intermediates, solvents, or mechanism; however, if more than one steps are
involved, you have to write the reagents in the correct order:
(a) ｜ (b)
／＼／＼ ／＼／︾ OH SH
｜ ｜ → ｜ ｜ ／＼／ → ／＼／
＼／ ＼／
(c) (d)
／〝／＼／ → 〃＼／＼／ ｜ ｜ OH
｜ ｜ ／＼／︾→ ／＼／＼／
5.Assign a systematic (IUPAC) name for each of the following compounds:
(a) ｜ (b) / (c)
／＼／＼ _/| ｜
｜ ║ ／/ ＼／＼ ＼／＼／〝／＼
＼／ ￣ ＼〃 /\ ｜
6.Predict the major product(s) for each of the following reactions. If more
than one stereoisomer is formed, draw all of them. For those with chiral
centers, use wedges and dashes to indicate the 3-D relationship. You don't
have to write down any intermediates and mechanisms. You also need not to
label the chiral centers.
(a) (b)
＿／ H2 ｜ H3O+
│║ ─────→ ／＼／〝／ ────→
￣＼ (PPh3)3RhCl
(c) (d) ╴ 1)MCPBA
｜ ｜ 1)BH3.THF ＼＿／￣＼＿／ ────→
／＼／︾─────→ ／ ＼ 2)H3O+
2)H2O2, OH-
7.Draw curved arrows for each step of the following mechanism:
+ H HO HO
O ／￣＼ O-H ／￣＼ \ ＼ ／￣＼ ＼
║ H2O+ OH ║ HO OH HO O＿／ HO OH HO O＿／
／＼ ────→ ／＼ ────→ \/ + ────→ \/
／＼ ／＼
｜
｜ ／￣＼
｜ H2O+ OH
↓
＿ ＿ HO
/ \ ／￣＼ +/ \ + ／＼ + ＼
O O HO OH H－O O O ｜ -H2O H2O O＿／
＼／ ←──── ＼／←──── ║ OH ←──── \/
/\ /\ ／＼ ／＼
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