作者xavier13540 (柊 四千)
看板NTU-Exam
标题[试题] 102暑 王宗兴 有机化学乙上 第二次期中考
时间Fri Mar 28 13:41:07 2025
课程名称︰有机化学乙上
课程性质︰暑修
课程教师︰王宗兴
开课学院：理学院
开课系所︰化学系
考试日期（年月日）︰2014/07/18
考试时限（分钟）：180
由於结构式用ascii画根本苦行 且就算用等宽字型也不保证读者能看到预期的结果 本篇所
有结构式皆用tex中的chemfig来呈现
考虑多数人并没有用过chemfig 这边简单介绍chemfig的解读方式
1. 单键是"-" 双键是"=" 三键是"~"
靠近读者的单键是"<"或">"
远离读者的单键是"<:"或">:"
若未指定 预设都是水平向右
设
b为任一种化学键 用"
b[:
n]"将
b逆时针旋转
n度
(以上皆不含引号)
2. 设
n为3以上的正整数 则"*
n(
t_1 t_2...t_n)"为一
n环 以正
n边形表示 其中
(1) 起点1在左下方 依逆时针编号为1, 2, ...,
n 且
n到1为垂直向下
更明确地说 i到i+1(这里规定顶点n+1即为顶点1)的辐角(argument)为i*360/
n-90度
(2) 连接i与i+1的化学键为
t_i
用"[:
m]*
n(
t_1 t_2...t_n)"将环逆时针旋转
m度
(以上皆不含引号)
3. 用圆括弧来画分枝
4. 用"\chemname{\chemfig{...}}{
caption}"(不含引号)在结构式下方加上
caption
一个范例是
\chemname{\chemfig{*4(-=-(<[:105]Br)(<:[:165]Br)-)}}{3, 3-dibromocyclobutene}
这张画出来的双键在正方形右边 长出来的两个溴在左上角
更多完整内容可以参阅官方网站的介绍：
http://mirrors.ctan.org/macros/generic/chemfig/chemfig-en.pdf
为了方便解读 以下题目的chemfig中 分支皆涂上其他颜色
试题 :
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话 似乎在课堂上听过的样子 第02话 那真是太令人绝望了
第03话 已经没什麽好期望了 第04话 被当、21都是存在的
第05话 怎麽可能会all pass 第06话 这考卷绝对有问题啊
第07话 你能面对真正的分数吗 第08话 我，真是个笨蛋
第09话 这样成绩，教授绝不会让我过的 第10话 再也不依靠考古题
第11话 最後留下的补考 第12话 我最爱的学分
--
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※ 编辑: xavier13540 (36.230.17.166 台湾), 04/02/2025 00:48:41
