課程名稱︰有機化學乙上
課程性質︰暑修
課程教師︰王宗興
開課學院：理學院
開課系所︰化學系
考試日期（年月日）︰2014/07/18
考試時限（分鐘）：180
由於結構式用ascii畫根本苦行 且就算用等寬字型也不保證讀者能看到預期的結果 本篇所
有結構式皆用tex中的chemfig來呈現
考慮多數人並沒有用過chemfig 這邊簡單介紹chemfig的解讀方式
1. 單鍵是"-" 雙鍵是"=" 三鍵是"~"
靠近讀者的單鍵是"<"或">"
遠離讀者的單鍵是"<:"或">:"
若未指定 預設都是水平向右
設b為任一種化學鍵 用"b[:n]"將b逆時針旋轉n度
(以上皆不含引號)
2. 設n為3以上的正整數 則"*n(t_1 t_2...t_n)"為一n環 以正n邊形表示 其中
(1) 起點1在左下方 依逆時針編號為1, 2, ..., n 且n到1為垂直向下
更明確地說 i到i+1(這裡規定頂點n+1即為頂點1)的輻角(argument)為i*360/n-90度
(2) 連接i與i+1的化學鍵為t_i
用"[:m]*n(t_1 t_2...t_n)"將環逆時針旋轉m度
(以上皆不含引號)
3. 用圓括弧來畫分枝
4. 用"\chemname{\chemfig{...}}{caption}"(不含引號)在結構式下方加上caption
一個範例是
\chemname{\chemfig{*4(-=-(<[:105]Br)(<:[:165]Br)-)}}{3, 3-dibromocyclobutene}
這張畫出來的雙鍵在正方形右邊 長出來的兩個溴在左上角
更多完整內容可以參閱官方網站的介紹：
http://mirrors.ctan.org/macros/generic/chemfig/chemfig-en.pdf
為了方便解讀 以下題目的chemfig中 分支皆塗上其他顏色
試題 :
1. Which of the following bromides is a better substrate for the preparation of
styrene using KOH/EtOH and heating? Explain your choice. (5%)
\chemfig{*6(=-=(-[:30]-[:-30]-[:30]Br)-=-)}
or
\chemfig{*6(=-=(-[:30](-[:90]Br)-[:-30])-=-)}
$\xrightarrow[\Delta]{\text{KOH, EtOH}}$
\chemname{\chemfig{*6(=-=(-[:30]=[:-30])-=-)}}{styrene}
2. The following bromide is unreactive toward elimination. Suggest a reason.
(6%)
\chemfig{[:-30]*6((<[:180](-[:120])(-[:-120])-[:180])---(<:Br)---)}
3. Assign E or Z configuration to the following compounds: (4%)
(a) \chemfig{(-[:120]H)(-[:-120]H_3CO)=(-[:60]Cl)(-[:-60]CH_3)}
(b) \chemfig{
(-[:120]H)(-[:-120]H_3C)=(-[:60](=[:120]O)-OCH_3)(-[:-60]CH_2OCH_3)
}
4. Explain the following observations: When tert-butyl bromide is treated with
sodium methoxide in a mixture of methanol and water, the rate of formation
of tert-butyl alcohol and tert-butyl methyl ether does not change apprecia-
bly as the concentration of sodium methoxide is increased. However, increa-
sing the concentration of sodium methoxide causes a marked increase in the
rate at which tert-butyl bromide disappears from the mixture. (10%)
5. Predict the organic product(s) of the following reactions. Indicate the ma-
jor product when there are two possible products. Specify the stereochemi-
stry when necessary. (30%)
(a) \chemfig{*6(--(-[:-30])=---)} $\xrightarrow[2)\text{NaBH}_4]{
1)\text{Hg(OAc)}_2, \text{CH}_3\text{OH}
}$
(b) \chemfig{-[:-30]-[:30]-[:-30](-[:90])(-[:-150])-[:-30]Br}
$\xrightarrow[\text{EtOH}, 50^\circ\text{C}]{\text{NaOEt}}$
(c) \chemfig{*6(--=(-[:30])---)} $\xrightarrow[\text{Pd/C}]{\text{D}_2}$
(d) \chemfig{-[:-30]-[:30]=[:90](-[:30])-[:150]-[:-150]}
$\xrightarrow[2)\text{Zn}, \text{CH}_3\text{COOH}]{
1)\text{O}_3, \text{CH}_2\text{Cl}_2, -78^\circ\text{C}
}$
(e) \chemfig{CH_3CH_2-~-H} $\xrightarrow[2)\text{D}_2\text{O}]{
1)\text{NaNH}_2
}$
(f) \chemfig{CH_3CH_2-~-CH_2-CHCH_3(-[:90]CH_3)} $\xrightarrow[\text{H}_2]{
\text{Lindlar's catalyst}
}$
(g) \chemfig{[:18]*5((-[:-126])=----)} $\xrightarrow[
2)\text{H}_2\text{O}_2, \text{NaOH}
]{
1)\text{BH}_3, \text{THF}
}$
(h) \chemfig{
*6((<[:-150](-[:-60])(-[:150])-[:-135])-(<[:-90]Cl)--(<:[:30])---)
} $\xrightarrow[\text{EtOH}, \Delta]{\text{NaOEt}}$
(i) \chemfig{Br-[:30]-[:-30]-[:30]-[:-30]-[:30]OH} $\xrightarrow[2)\Delta]{
1)\text{NaH}, \text{Et}_2\text{O}
}$
(j) \chemfig{*6(---(<[:30]Cl)--(<:[:150])-)} $\xrightarrow[\text{DMSO}]{
\text{NaSH}
}$
(k) \chemfig{-[:30]-[:-30](-[:-90]-[:-30])-[:30](-[:90]Br)-[:-30]}
$\xrightarrow[\text{BuOH}]{t\text{-BuOK}}$
(l) \chemfig{-[:60]=-[:60]} $\xrightarrow{\text{Br}_2, \text{H}_2\text{O}}$
Draw your answer using Fischer projection
(m) (R)-2-Bromobutane $\xrightarrow[\text{CH}_3\text{OH}, 25^\circ\text{C}]{
\text{NaSCH}_3
}$
(n) \chemfig{[:30]*6(-=(-)----)} $\xrightarrow[\text{H}_2\text{O}]{
\text{cat. H}_2\text{SO}_4
}$
(o) \chemfig{-[:-60]=-[:60]} $\xrightarrow[\text{CHCl}_3]{t\text{-BuOK}}$
6. Propose a mechanism that explains formation of the products from the follo-
wing reaction, including the distribution of the products as major and mi-
nor. Draw curved arrows to indicate electron flow in each step. (10%)
2 \chemfig{-[:30](-[:90])=[:-30]} $\xrightarrow{
\text{H}_2\text{SO}_4\text{(cat.)}
}$ \chemname{
\chemfig{-[:30](-[:90])(-[:-105])-[:-30]-[:30](=[:90])-[:-30]}
}{major} + \chemname{
\chemfig{-[:30](-[:90])(-[:-105])-[:-30]=[:30](-[:90])-[:-30]}
}{minor}
7. Propose a reasonable mechanism for the following reaction:
\chemfig{-[:30]-[:-30]-[:30]-[:-30]OH} $\xrightarrow{
\text{H}^+, \text{heat}
}$ \chemfig{-[:30]=[:-30]-[:30]}
Draw curved arrows to indicate electron flow in each step. (5%)
8. There are two carboxylic acids with the general formula \chemfig{
HO_2CCH=CHCO_2H}. When treated with \chemfig{OsO_4}, followed by \chemfig{
NaHSO_3}/\chemfig{H_2O}, one acid yields meso-tartaric acid and the other
acid yields (±)-tartaric acid. Determine the stereochemical formulas for
the two acids and explain your answer. (10%)
9. When trans-2-methylcyclohexanol is subjected to acid-catalyzed dehydration,
the major product is 1-methylcyclohexene:
\chemfig{*6(---(<:[:30]OH)-(<[:90])--)} $\xrightarrow[\text{heat}]{
\text{HA}
}$ \chemfig{*6(---=(-[:90])--)}
However, when trans-1-bromo-2-methylcyclohexane is subjected to dehydrohalo-
genation, the major product is 3-methylcyclohexene: (10%)
\chemfig{*6(---(<:[:30]Br)-(<[:90])--)} $\xrightarrow[\text{EtOH, heat}]{
\text{EtONa}
}$ \chemfig{*6(--=-(-[:90])--)}
10. Complete the tollowing synthesis. You may use any other needed reagents.
(10%)
(a) ethyne → 3-heptyne
(b) \chemfig{*6(---(-[:30]OH)(-[:90])---)} → \chemfig{
*6(--(<:[:-30]OH)-(<[:30])---)
}
--
第01話 似乎在課堂上聽過的樣子 第02話 那真是太令人絕望了
第03話 已經沒什麼好期望了 第04話 被當、21都是存在的
第05話 怎麼可能會all pass 第06話 這考卷絕對有問題啊
第07話 你能面對真正的分數嗎 第08話 我，真是個笨蛋
第09話 這樣成績，教授絕不會讓我過的 第10話 再也不依靠考古題
第11話 最後留下的補考 第12話 我最愛的學分
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※ 編輯: xavier13540 (36.230.17.166 臺灣), 04/02/2025 00:48:41