作者oliver1089 (鲔鱼)
看板NTU-Exam
标题[试题] 100上 杨吉水 有机化学乙 第二次期中(2)
时间Mon Jan 16 21:22:21 2012
课程名称︰有机化学
课程性质︰必带
课程教师︰杨吉水
开课学院：工学院
开课系所︰化工系
考试日期（年月日）︰2011/12/01
考试时限（分钟）：110
是否需发放奖励金：是
（如未明确表示，则不予发放）
试题 :
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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