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series
homologous series
give systematic names, general formulae,
structural formulae and systematic
condensed formulae and structural formulae for:
naming
alkanes, alkenes, haloalkanes, alcohols, aldehydes
carbon compounds
1
Topic Students should learn Students should be able to Notes
XI (a) Introduction to selected homologous series give systematic names, general formulae, condensed Students should be able to give systematic names of alkanes,
homologous series
formulae and structural formulae for: alkanes, alkenes, alkenes, haloalkanes, alcohols, aldehydes and ketones,
structural formulae and
haloalkanes, alcohols, aldehydes and ketones,
carboxylic acids, esters, unsubstituted amides and primary
systematic naming
amines with carbon chains not more than eight carbon atoms
carboxylic acids, esters, unsubstituted amides and
(mentioned in the overview of the topic in the Guide).
primary amines
Students should be able to give systematic names for organic
draw the structures of the compounds based on
compounds with multiple functional groups of the same type,
their systematic names
e.g. propane-1,2,3-triol. For other compounds with
multiple functional groups, the use of order of priority of
principal functional groups is not expected.4
Students should be able to give systematic names for organic
compounds with unsaturated carbon-carbon bonds and/or
halogen substituents, e.g. 3,3-dichloropropene and
2-bromopent-3-en-1-ol.
4
Reference: http://www.acdlabs.com/iupac/nomenclature/93/r93_326.htm
2
課題 十一 碳化 合物 的化 學
學生應學習 學生應能
a. 特定同系列的簡介
• 同系列
• 寫出以下化合物的系統名稱、通
• 結構式與系統命名法
式、簡 明 結 構 式 和 結 構 式: 烷 烴 、
烯烴、鹵烷、醇、醛和酮、羧酸、
酯、未經取代的酰胺和一級胺
• 根據化合物的系統名稱繪出其結
構
• 明 瞭 官 能 基 及 碳 鏈 長 度 對 碳
化 合 物 的物理性質的影響
• 辨 認 一 些 碳 化 合 物 的 通 俗 名 稱,如
蟻醛、氯仿、丙酮、異丙醇、醋
酸
3
課題 學生應學習 學生應能 說明
十一(a) 特定同系列的簡介 寫出以下化合物的系統名稱、通式、簡明結構式
學生應能寫出碳鏈帶著不多於八個碳原子的烷烴、烯烴、鹵 烷、醇、醛和酮、羧酸、酯、
同系列
未經取代的酰胺和一級胺的系統名稱。(在指引內課題概述中已說明)
和結構式:烷烴、烯烴、鹵烷、醇、醛和酮、羧
學生應能寫出多於一個相同官能基的有機化合物的系統名稱, 例如丙-1,2,3-三醇。學生不
結構式與系統命名法
酸、酯、未經取代的酰胺和一級胺 需運用主官能基的優先次序來命名其他含多個官能基的有機化合物。4
根據化合物的系統名稱繪出其結構 學生應能寫出含不飽和碳碳鍵和/或鹵取代基的有機化合物的系統名稱,例如 3,3-二氯丙
烯和 2-溴戊-3-烯-1-醇。
4
參考資料: http://www.acdlabs.com/iupac/nomenclature/93/r93_326.htm
4
Homologous series
同系列
- A series of compounds, which can fit the same general formula, is called a homologous
series.
由具同一通式的一組化合物組成的系列稱為同系列。
Name of homologous
Chemical formula 1st member
series
化學式 首成員
同系列的名稱
Alkanes
烷 CH4, C2H6, C3H8, C4H10 … CH4
CnH2n+2
Alkenes
烯 C2H4, C3H6, C4H8 … H2C=CH2
CnH2n (C=C)
Haloalkanes
鹵烷 CH3X, CH3CH2X, CH3CH2CH2X … CH3X
RX (X = halogen)
Alkanol
CH3OH, CH3CH2OH, CH3CH2CH2OH,
烷醇 CH3OH
CH3CH2CH2CH2OH …
ROH
Carboxylic acid
HCOOH, CH3COOH, CH3CH2COOH,
羧酸 HCOOH
CH3CH2CH2COOH …
RCOOH
Aldehyde
CH3CHO, CH3CH2CHO,
醛 HCHO
CH3CH2CH2CHO…
RCHO
Ketone
CH3COCH3, CH3COCH2CH3,
酮 CH3COCH3
CH3CH2COCH2CH3…
RCOR’
Primary amine
一級胺 CH3NH2, CH3CH2NH2, CH3CH2CH2NH2… CH3NH2
RNH2
Unsubstituted amides
未經取代的酰胺 HCONH2, CH3CONH2, CH3CH2CONH2… HCONH2
RCONH2
5
Ester
HCOOCH3, CH3COOCH3,
酯 HCOOCH3
CH3COOCH2CH3…
RCOOR’
Q1: Which of the following compounds is the first member of a homologous series?
以下哪化合物屬某同系列中的首成員?
A. C2H6
B. CH3CHO
C. HCOOH
D. CH3CH3Br
Q2: Which of the following species is the molecular formula of carboxylic acid?
以下哪物種是羧酸的分子式?
A. CHO
B. CH2O
C. C2H2O
D. C2H4O2
6
Each member in a homologous series differs from the next by a
-CH2 unit.
相鄰成員的分子結構相差一個-CH2 單位。
Example:
Example:
The number of carbon atom in molecule increases (Relative molecular mass increases),
分子內的碳原子數增加 (相對分子質量增加),
Example:
Alkane can undergo combustion.
烷烴可進行燃燒。
7
Structural formula and molecular formula
結構式和分子式
Example:
Compound A Compound B
Structural formula can show the bond between atoms and how the atoms in a molecule
are joined to each other.
結構式可展出原子之間的鍵和分子內的原子如何結合。
Condensed structural formula can also be used to express the structural formula in a
simplified form.
使用簡化結構式可用作簡單展示結構式。
8
Molecular Condensed
IUPAC name Structural formula
formula structural formula
系統名稱 結構式
分子式 簡化結構式
H H H H H
Pentane
C5H12 H C C C C C H CH3(CH2)3CH3
戊烷
H H H H H
H H H H
But-2-ene
C4H8 H C C C C H CH3CH=CHCH3
丁-2-烯
H H
H H
Ethanol
C2H6O H C C O H CH3CH2OH
乙醇
H H
H O
Ethanoic acid
C2H4O2 H C C O H CH3COOH
乙酸
H
H O H
Propanone
C3H6O H C C C H CH3COCH3
丙酮
H H
H O
Ethanal
C2H4O H C C H CH3CHO
乙醛
H
H H O H H
Ethyl
propanoate C5H10O2 H C C C O C C H CH3CH2COOCH2CH3
丙酸乙酯 H H H
H
H H O H
Propanamide
C3H7NO H C C C N H CH3CH2CONH2
丙酰胺
H H
H H H
Ethanamine
C2H7N H C C N H CH3CH2NH2
乙胺
H H
9
Alkanes and Alkenes
烷和烯
- The general formula of alkanes: CnH2n+2
烷的通式:
它們不溶於水。
It is because the non-polar van der Waals’ forces between alkane / alkene molecules are
weaker than the hydrogen bond between water molecules.
由於烷/烯的分子間具非極性范德華力,比水分子間的氫鍵較弱。
It is because the non-polar van der Waals’ forces between alkane / alkene molecules are of
comparable strength as those in molecules of organic solvents.
由於烷/烯的分子間的非極性范德華力與有機溶劑分子間的引力強度相若。
10
- They are less dense than water.
它們的密度比水低。
It is because the non-polar van der Waals’ forces between alkanes / alkenes molecules are
much weaker than the hydrogen bonds between water molecules.
是因為烷 / 烯分子間的非極性范德華力比水分子間的氫鍵較弱。
Therefore, alkanes / alkenes molecules pack less efficiently than water molecules.
所以,烷 / 烯分子排列比水分子較不有效。
碳原子數目增加)而上升。
It is because the strength of van der Waals’ forces increases as the molecular size increases.
是由於隨分子大小增加,分子間的范德華力強度增加。
11
2021DSEM IB (2 marks)
Which of octane, pentane and ethene would have the highest boiling point? Explain your
answer.
辛烷、戊烷和乙烯,何者具最高沸點? 解釋你的答案。
Solution:
Octane
辛烷 1M
The molecular size of octane is the greatest so that the van der Waals’ forces between
octane molecules are the strongest.
辛烷的分子體積是最大的,所以辛烷分子間的范德華力是最強。 1M
Solution:
12
Systematic nomenclature (IUPAC) of alkanes and
alkenes
烷和烯的系統命名法 (IUPAC)
詞頭 + 根 + 詞尾
13
Steps for naming alkanes
命名烷的步驟
找出最長的連續碳主鏈。
命名烴鏈 = 根。
Number of
C atom 1 2 3 4 5 6 7 8 9 10
C 原子數
Root meth- eth- prop- but- pent- hex- hept- oct- non- dec-
根 甲 乙 丙 丁 戊 己 庚 辛 壬 癸
丙烷
14
4. Adding the prefixes.
加入詞頭。
- All the prefixes (substituents) are added in alphabetical order.
所有詞頭 (取代基) 以字母次序排列。
- di, tri and tetra are not considered.
二、三、四不需要考慮。
取代基只作詞頭的命名
Aryl phenyl
芳基取代物 -C6H5 or 苯基
Example: CH3CH(C2H5)CH(CH3)CH(CH3)CH2CH2CH2CH3
2-ethyl-3,4-dimethlyoctane
2-乙基-3,4-二甲基辛烷
15
5. Adding numbers, commas and hyphens
加入編號、逗號和連字號
Example: 1,3,5-trichloropentane
1,3,5-三氯戊烷
Example: methylpropane
甲基丙烷
16
Q2: Give the systematic name for the following organic compounds:
寫出以下有機化合物的系統名稱:
(a) CH3CH2CH(CH3)CH2CH2CH3
________________________________________________________________
(b) CH3CH(C2H5)CH2CH(CH3)CH2CH2CH3
_________________________________________________________________
(c) CH3CH(CH3)CH2CH(CH3)CH2CH3
_________________________________________________________________
(d) CH3CH2CH2CH(C2H5)CH(C2H5)CH2CH2CH3
_________________________________________________________________
17
Steps for naming alkenes
命名烷的步驟
命名烴鏈 = 根。
Example: CH3CHClCHBrCHClCH2CH2=CH2
5-bromo-4,6-dichlorohept-1-ene
5-溴-4,6-二氯庾-1-烯
18
5. Adding numbers, commas and hyphens
加入編號、逗號和連字號
2017DSEM IB #5 (63%)
What is the systematic name of Br2CH-CH=CH-CH=CH2?
Br2CH-CH=CH-CH=CH2 的系統名稱是什麼?
A. 1-dibromopenta-2,4-diene
1-二溴戊-2,4-二烯
B. 5,5-bromopenta-1,3-diene
5,5-溴戊-1,3-二烯
C. 1,1-dibromopenta-2,4-diene
1,1-二溴戊-2,4-二烯
D. 5,5-dibromopenta-1,3-diene
5,5-二溴戊-1,3-二烯
19
Q4: Give the systematic name for the following organic compounds:
寫出以下有機化合物的系統名稱:
20
Alkanols (烷醇)
O
R H
Alkyl group Hydroxyl group
烷基 羥基團
(hydrophobic) (hydrophilic)
(疏水) (親水)
H R' R'
R C OH R C OH R C OH OH
H H R''
21
Q5: Classify the following alcohol into primary, secondary and tertiary.
試把下列酒精分類為一級、二級和三級。
(a)
OH 1°ROH / 2°ROH / 3°ROH
(b)
OH 1°ROH / 2°ROH / 3°ROH
(c) OH
(d)
OH
(e)
OH 1°ROH / 2°ROH / 3°ROH
(f)
1°ROH / 2°ROH / 3°ROH
OH
(g)
1°ROH / 2°ROH / 3°ROH
OH
(h)
1°ROH / 2°ROH / 3°ROH
OH
(i) OH
1°ROH / 2°ROH / 3°ROH
22
Physical properties of Alkanols
烷醇的物理性質
- Alkanol with small molecular size ( 4C) are soluble in water. The solubility of ROH in water
decreases as the length of the hydrophobic hydrocarbon chain increases.
分子體積細小的烷醇 (< 4C) 可溶於水。ROH 在水中的溶解度隨疏水性烴鏈的長度增加而下
降。
The hydroxyl groups in alkanol can form hydrogen bonds with water.
醇的羥基團能與水形成氫鍵。
NOTE: The solubility of an organic compound in water depends on the nature of the
functional group and the length of hydrophobic hydrocarbon chain.
有機化合身在水中的溶解度取決於官能基的性質與疏水性烴鏈的長度。
- ROH with small molecular size has polar hydroxyl group (-OH) and a short hydrocarbon chain,
therefore they can form strong hydrogen bonds with water molecules and they are water
soluble.
分子體積細小的 ROH 有帶極性的羥基(-OH)和短烴鏈,所以它們可與水分子形成氫鍵,並且可
溶於水。
ROH with large molecular size has polar hydroxyl group (-OH) and a long hydrocarbon chain,
therefore they have weak attraction with water molecules and they are water insoluble.
分子體積大的 ROH 有帶極性的羥基(-OH)和長烴鏈,所以它們與水分子的吸力很弱,並在水中
的溶解度很低。
23
2014DSEM IB #2
Draw the structure of propane-1,3-diol, and suggest whether it is soluble in water.
繪出丙-1,3-二醇的結構,並提出它是否可溶於水。 (3 marks)
Solution:
HO OH 1M
24
- Due to the hydrogen bonds formed between the molecules of alkanols, their boiling point and
melting point are higher than alkanes and alkenes with a similar relative molecular mass.
由於烷醇分子間有氫鍵,它們的沸點和熔點高於有相若相對分子質量的烷和烯。
Example:
.. ..
O
H CH2CH3
.. ..
O
CH3CH2 H
. . ..
O
H CH2CH3
25
Systematic nomenclature (IUPAC) of alkanols
烷醇的系統命名法 (IUPAC)
1. Find the longest continuous carbon chain contains the hydroxyl group (-OH).
找出有羥基(-OH)的最長連續碳主鏈。
命名烴鏈 = 根。
26
4. Adding the prefixes.
加入詞頭。
- All the prefixes (substituents) are added in alphabetical order.
所有詞頭 (取代基) 以字母次序排列。
- di, tri and tetra are not considered.
二、三、四不需要考慮。
Example: CH3CHClCHClCH2CH2CHBrCH2OH
2-bromo-5,6-dichloroheptan-1-ol
2-溴-5,6-二氯庚-1-醇
Example: Ethanol
乙醇
27
Q5: Give the systematic name for the following organic compounds:
寫出以下有機化合物的系統名稱:
28
Carboxylic acids (羧酸)
- They have a characteristic pungent smell and sour taste.
它們有獨特的辛辣味和酸味。
C
R O H
29
Physical properties of carboxylic acids
羧酸的物理性質
- RCOOH with small molecular size has polar carboxyl group (-COOH) and a short hydrocarbon
chain, therefore they can form strong hydrogen bonds with water molecules and they are
water soluble.
分子體積細小的 RCOOH 有帶極性的羧基(-COOH)和短烴鏈,所以它們可與水分子形成氫鍵,
並且可溶於水。
RCOOH with large molecular size has polar carboxyl group (-COOH) and a long hydrocarbon
chain, therefore they have weak attraction with water molecules and they are water
insoluble.
分子體積大的 RCOOH 有帶極性的羧基(-COOH)和長烴鏈,所以它們與水分子的吸力很弱,並
在水中的溶解度很低。
- RCOOH has higher boiling point / melting point than ROH with similar molecular mass
because ROOH forms more extensive hydrogen bond between molecules than ROH.
ROOH 與相近分子質量的 ROH 比有較高的沸點/熔點,這是由於 RCOOH 比 ROH 生成更多的
分子間氫鍵。
30
Q6: Consider the following information:
考慮以下資料:
Explain why ethanoic acid has a higher boiling point than ethanol? Suggest a suitable
method to separate ethanoic acid from a mixture of ethanol and ethanoic acid.
解釋為何乙酸比乙醇有較高的沸點? 提出一項適當的方法把乙酸從乙醇和乙酸的混
合物中分離出來。 (3 marks)
31
Systematic nomenclature (IUPAC) of carboxylic acids
羧酸的系統命名法 (IUPAC)
1. Find the longest continuous carbon chain contains the carboxyl group ‘-COOH’.
找出有羧基 ‘-COOH’的最長連續碳主鏈。
命名烴鏈 = 根。
32
If ONE -COOH group is in a benzene ring, it called benzoic acid.
若一個-COOH 基團位於苯環上,它被稱為苯酸。
Example:
Benzoic acid
苯酸
3-methylbenzoic acid
3-甲基苯酸
If more than one -COOH group are located on a benzene ring, the suffix is
‘carboxylic acid’.
若多於一個-COOH 基團位於苯環上,詞尾是「羧酸」。
Example: CH2ClCH=CHCH=CHCHBrCOOH
2-bromo-7-chlorohept-3,5-dienoic acid
2-溴-7-氯庚-3,5-二烯酸
33
5. Adding numbers, commas and hyphens
加入編號、逗號和連字號
34
Q7: Give the systematic name for the following organic compounds:
寫出以下有機化合物的系統名稱:
(e)
________________________________________
(f)
__________________________________________
(g)
_________________________________________
35
Haloalkanes (鹵烷)
R X
Alkyl group (烷基) Halogen (鹵素)
- Usually non-flammable.
通常是不易燃的。
Br Br
Cl C F F C F
F F
BCF BTM
36
Physical properties of haloalkanes
鹵烷的物理性質
It is because the van der Waals’ forces between RX molecules are weaker than
the hydrogen bond between water molecules.
由於 RX 的分子間具范德華力,比水分子間的氫鍵較弱。
RX molecules have weak attraction with water molecules and they are insoluble in water.
RX 分子與水分子的吸力很弱,並且不溶於水。
- As the larger relative atomic masses of the halogen atoms and the stronger van der Waals’
forces, RX are denser than water.
由於鹵原子有較大的相對原子質量和較強的范得華力,RX 的密度比水高。
- Due to the polar van der Waals’ forces between the molecules of RX, their boiling point and
melting point are higher than alkanes and alkenes with a similar relative molecular mass.
由於 RX 分子間存在極性范德華力,它們的沸點和熔點高於有相若相對分子質量的烷和烯。
37
Example:
Account for the trends of boiling point of the following RX:
解釋下列 RX 沸點的趨向:
Boiling point (沸點): CH3CH2I > CH3CH2Br > CH3CH2Cl > CH3CH2F
Solution:
The boiling point increases from CH3CH2F to CH3CH2I, it is due to the increased molecular
size. So, the molecule has stronger intermolecular forces as the molecular size increases.
沸點由 CH3CH2F 增加至 CH3CH2I,是由於分子大小增加,分子大小增加,所以有更強的分子
間引力。
38
Systematic nomenclature (IUPAC) of haloalkanes
鹵烷的系統命名法 (IUPAC)
Example:
(a) CH3CHBrCHClCH2CH2CH3 2-bromo-3-chlorohexane
2-溴-3-氯己烷
(c) 1,3,5-tribromobenzene
1,3,5-三溴苯
(d) CH3CBrCH2CH2CH2CH2OH
(e) CH3CH=CHCH2CClCH2COOH
39
Aldehydes and Ketones
醛和酮
- They are carbonyl compounds.
它們是羰基化合物。
O O
Aldehyde Ketone
醛 酮
40
Physical properties of aldehydes and ketones
醛和酮的物理性質
Aldehydes and ketones with large molecular size has polar carbonyl group (>C=O) and a
long hydrocarbon chain, therefore they have weak attraction with water molecules and they
are water insoluble.
分子體積大的醛和酮有帶極性的羰基(>C=O)和長烴鏈,所以它們與水分子的吸力很弱,並在
水中的溶解度很低。
Aldehydes and ketones with small molecular size has polar carbonyl group (>C=O) and a
short hydrocarbon chain, therefore they can form strong hydrogen bonds with water
molecules and they are water soluble.
分子體積細小的醛和酮有帶極性的羰基(>C=O)和短烴鏈,所以它們可與水分子形成氫鍵,並
且可溶於水。
- Aldehydes and ketones have higher melting point and boiling point than alkanes and alkenes
with similar molecular masses because the polar molecules have strong intermolecular
attraction.
醛和酮比有相若分子質量的烷和烯有較高的沸點和熔點,因為其極性分子間有較強的分子間引
力。
41
Systematic nomenclature (IUPAC) of aldehydes and
ketones
醛和酮的系統命名法 (IUPAC)
1. Find the longest continuous carbon chain contains the -CHO group.
找出有-CHO 鍵的最長連續碳主鏈。
命名烴鏈 = 根。
42
Steps for naming ketones
命名酮的步驟
1. Find the longest continuous carbon chain contains the >C=O group.
找出有>C=O 鍵的最長連續碳主鏈。
命名烴鏈 = 根。
43
Q8: Give the systematic name for the following organic compounds:
寫出以下有機化合物的系統名稱:
44
Esters (酯)
- Esters are carboxylic acid derivatives. O
酯是羧酸的衍生物。
RCOOR’ with large molecular size has polar ester group (-COO-) and a long hydrocarbon
chain, therefore they have weak attraction with water molecules and they are water
insoluble.
分子體積大的 RCOOR’有帶極性的酯基(-COO-)和長烴鏈,所以它們與水分子的吸力很弱,並
在水中的溶解度很低。
RCOOR’ with small molecular size has polar ester group (-COO-) and a short hydrocarbon
chain, therefore they can form strong hydrogen bonds with water molecules and they are
water soluble.
分子體積細小的 RCOOR’有帶極性的酯基(-COO-)和短烴鏈,所以它們可與水分子形成氫鍵,
並且可溶於水。
45
2022DSEM IA #9 (20%)
Consider the following three organic compounds:
考慮以下三個有機化合物:
Which of the following shows the increasing order of their solubilities in water?
下列何者顯示它們在水中溶解度的遞增次序?
A. Y<X<W B. W<X<Y
C. W<Y<X D. Y<W<X
46
- Due to the polar van der Waals’ forces formed between the molecules of esters,
their boiling point and melting point are similar to aldehydes and ketones with a
similar relative molecular mass.
由於酯分子間的極性范德華力,其沸點和熔點與有相若相對分子質量的醛和酮相近似。
Since polar van der Waals’ forces are weaker than hydrogen bond, their boiling
point and melting point are lower than alkanols and carboxylic acids with a
similar relative molecular mass.
由於極性范德華力比氫鍵弱,它們的沸點和熔點低於有相若相對分子質量的烷醇和羧酸。
The intermolecular attraction between ester molecules is weaker than that between water
molecules.
酯的分子間引力比水分子間的較弱。
47
Systematic nomenclature (IUPAC) of esters
酯的系統命名法 (IUPAC)
CH3CH2 C O CH2CH3
根 + 酸 根 + 酯 答案: 丙酸乙酯
1. The RO- part (come from ROH) in the ester molecule is named first. Using the root name and
ended with ‘yl’.
2. The R’CO- part (come from R’COOH) is then named by using the root name and ended with
‘anoate’.
48
Q9: Give the systematic name for the following organic compounds:
寫出以下有機化合物的系統名稱:
(a) O
CH3 C O CH3
_____________________________
(b) O
CH3CH2CH2 C O CH2CH3
_____________________________
O
(c)
CH3CH2 O C CH3
_____________________________
(d) O
CH3CH2CH2 O C H _____________________________
49
Unsubstituted amides
未經取代的酰胺
C H
R N
H
Exception: HCOONH2(l)
50
Physical properties of unsubstituted amides
未經取代的酰胺的物理性質
- RCONH2 with large molecular size has polar amide group (-CONH2) and a long hydrocarbon
chain, therefore they have weak attraction with water molecules and they are water
insoluble.
分子體積大的 RCONH2 有帶極性的酰胺基(-CONH2)和長烴鏈,所以它們與水分子的吸力很弱,
並在水中的溶解度很低。
RCONH2 with small molecular size has polar amide group (-CONH2) and a short hydrocarbon
chain, therefore they can form strong hydrogen bonds with water molecules and they are
water soluble.
分子體積細小的 RCONH2 有帶極性的酰胺基(-CONH2)和短烴鏈,所以它們可與水分子形成氫
鍵,並且可溶於水。
- Due to the more extensive intermolecular hydrogen bonds formed between the
molecules of unsubstituted amides, their boiling point and melting point are
higher than alkanols and carboxylic acids with a similar relative molecular mass.
由於未經取代的酰胺分子間有伸展性較高的分子間鍵鍵,其沸點和熔點高於有相若相對分子
質量的烷醇和羧酸。
51
Systematic nomenclature (IUPAC) of unsubstituted
amide
未經取代的酰胺的系統命名法 (IUPAC)
1. Find the longest continuous carbon chain contains the -CONH2 group.
找出有-CONH2 鍵的最長連續碳主鏈。
命名烴鏈 = 根。
52
Q10: Give the systematic name for the following organic compounds:
寫出以下有機化合物的系統名稱:
(a) CH3 O
CH3CH2CHCH2CH2CH2CH2-C NH2
______________________________
(b) O
______________________________
(c) O
CH2CH2C-NH2 ______________________________
53
Primary amines
一級胺
.. .. ..
R N H R N R' R N R'
H H R''
- They are formed by substituting hydrogen atoms in NH3 with alkyl groups.
它們是經烷基取代 NH3 上的氫所生成。
54
Physical properties of primary amines
一級胺的物理性質
- RNH2 with large molecular size has polar amino group (-NH2) and a long hydrocarbon chain,
therefore they have weak attraction with water molecules and they are water insoluble.
分子體積大的 RNH2 有帶極性的胺基(-NH2)和長烴鏈,所以它們與水分子的吸力很弱,並在水
中的溶解度很低。
RNH2 with small molecular size has polar amino group (-NH2) and a short hydrocarbon chain,
therefore they can form strong hydrogen bonds with water molecules and they are water
soluble.
分子體積細小的 RNH2 有帶極性的胺基(-NH2)和短烴鏈,所以它們可與水分子形成氫鍵,並且
可溶於水。
- Hydrogen bonds formed between the molecules of primary amines. As the electronegativity
of nitrogen is lower than oxygen, N-H bond is less polar than O-H bond. their boiling point
and melting point are lower than alkanols and carboxylic acids with a similar relative
molecular mass.
一級胺的分子間存在氫鍵,由於氮的電負性比氧低,N-H 鍵比 O-H 鍵的極性較弱。 它們的
沸點和熔點低於有相若相對分小質量的烷醇和羧酸。
55
Systematic nomenclature (IUPAC) of primary amine
一級胺的系統命名法 (IUPAC)
1. Find the longest continuous carbon chain contains the amino group (-NH2).
找出有胺基(-NH2)的最長連續碳主鏈。
命名烴鏈 = 根。
CH2ClCH2CH=CHCH2CH2CH2CH2NH2 8-chlorooct-5-en-1-amine
8-氯辛-5-烯-1-胺
CH3CH2CH2CHCH2CHCH2CH3 Octane-3,5-diamine
辛-3,5-二胺
NH2 NH2
56
Trivial names of some common
organic compounds
一些有機化合物的通俗名稱
- No systematic principles in assigning the trivial names.
命名通俗名稱是沒有系統原理的。
1. Methanal HCHO
甲醛
2. Propanone CH3COCH3
丙酮
Uses: Solvent
用途: 溶劑
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3. Propan-2-ol CH3CH(OH)CH3
丙-2-醇
5. Trichloromethane CHCl3
三氯甲烷
58
Q12: Give the structural formula of the following compounds.
舉出下列化合物的結構式。
4,5-二甲基己-1-烯 丁酸丙酯
丙酸乙酯 4-甲基己-3-酮
3-氯己-2-酮 4,4-二甲基庚-1-烯-3-酮
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(11) 2,4-dichlorohexan-1-ol (12) 2-methylpentanoic acid
2,4-二氯已-1-醇 2-甲基戊酸
60
Summary
With similar relative molecular masses and molecular shape, the order
of boiling point and melting point as follows:
有相若的相對分子質量和分子形狀,沸點和熔點的排列次序如下:
Unsubstituted amide > carboxylic acid > alcohol > primary amine >
CnH2n+2、CnH2n 和 RX 都不溶水。
積都是可溶水的。它們的溶解度隨烴鏈長度增加而下降。
61
Q1: Which of the following compound has the highest melting point?
以下哪化合物有最高的熔點?
A. B.
OH Cl
C. O D.
OH
Q2: Which of the following compound has the lowest boiling point?
以下哪化合物有最低的沸點?
A. B. O
NH2
OH
C. D.
OH
C. O D. O
H OH
62
Q4: Which of the following compound has the highest solubility in water?
以下哪化合物於水中有最高的溶解度?
A. B. O
Cl
C. OH D. O
OH
O
Q5: Which of the following compound has the highest boiling point?
以下哪化合物有最高的沸點?
A. O B. OH
C. D.
O
NH2
Q6: Which of the following compound has the lowest melting point?
以下哪化合物有最低的熔點?
A. O B.
C. D.
63
2019DSEM IB #6b (ii)
Explain why CBr4 has a higher boiling point than CH2Br2. (2 marks)
解釋為什麼 CBr4 比 CH2Br2 具較高的沸點。
Solution:
CBr4 has a larger molecular size than that of CH2Br2. 1
CBr4 的分子體積較 CH2Br2 的為大。
Therefore, it has stronger van der Waals’ forces between molecules / intermolecular forces,
and hence a higher boiling point. 1
所以在 CBr4 分子間的范德華力/分子間引力較強,故具較高沸點。
Solution:
Octane 1
辛烷
The molecular size of octane is the greatest so that the van der Waals’ forces between
octane molecules are the strongest. 1
辛烷的分子體積是最大的,所以辛烷分子間的范德華力是最強。
64
Q7: Explain the following increasing order of the boiling points of the three organic
compounds:
解釋以下這三個有機化合物的沸點遞增次序:
Solution:
65
HOMEWORK
Exercise 1:
(a) (b) (c) (d)
CH2CH3 CH3CH2-CH-CH2CH3 OH
CH3CH2CH2CH=CHCOOH CH3CH=CHCH2CH2OH CH3CH
CH3CH2CH2CH2-C-CH2CH3 CH2CH=CH2 CH3CHCH2CH2COOH
Cl
HO-CH2-C=CH-CH2-C C-H OH
HC CCH2CH2CH2OH HC CCH2CHCH2CH2OH
CH3
Br CH2CH3
CH2CH3 CH3-CH Cl
CH3
CH3
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(n) (o) (p)
NH2 CH=CH2
Cl OH
CH2CH2COOH CH2CH2OH
CH3-CH CH3CH2CH=CH
CH3
CH3
(z) HCOOCH2CH3
67
Solution of exercise 1:
(a) 3-chloro-3-ethylheptane 3-氯-3-乙基庚烷
(b) 4-ethylhex-1-ene 4-乙基己-1-烯
(c) hex-2-enoic acid 己-2-烯酸
(d) pent-3-en-1-ol 戊-3-烯-1-醇
(e) pent-4-yn-1-ol 戊-5-炔-1-醇
(f) 2-methylhex-2-en-5-yn-1-ol 2-甲基己-2-烯-5-炔-1-醇
(g) hex-5-yne-1,3-diol 己-5-炔-1,3-二醇
(h) 1-chloro-2-ethylbenzene 1-氯-2-乙基苯
(i) 5-bromo-2-methylbenzoic acid 5-溴-2-甲基苯酸
(j) 2-bromo-6-ethylbenzoic acid 2-溴-6-乙基苯酸
(k) 2-phenylethanol 2-苯基乙醇
(l) 3-ethylbenzene-1,2-dicarboxylic acid 3-乙基苯-1,2-二羧酸
(m) (methylethyl)benzene (甲基乙基)苯
(n) 3-phenlypropanoic acid 3-苯基丙酸
(o) 2-(2-chlorophenyl)ethanol 2-(2-氯苯基)乙醇
(p) phenylethene 苯基乙烯
(q) Butanone 丁酮
(r) 2,4-dimethylpentan-3-one 2,4-二甲基戊-3-酮
(s) 1-phenylpropan-1-one 1-苯基丙-1-酮
(t) ethanal 乙醛
(u) 4-bromo-3-methylheptanal 4-溴-3-甲基庚醛
(v) Pent-2-enal -2-烯醛
(w) Butanone 丁醛
(x) 3,5-dimethylheptan-4-one 3,5-二甲基庚-4-酮
(y) Methyl propanoate 丙酸甲酯
(z) Ethyl methanoate 甲酸乙酯
68
Exercise 2:
Give the structural formula of the following compounds.
舉出下列化合物的結構式。
(m) butanal 丁醛
(n) butanone 丁酮
69
Solution of exercise 2:
(a) (b) (c)
CH3 CH2 CH=CH2 CH3 CH2 COONa CH3 CH2 NH2
Cl Cl CH3CH2 COOH
CH3 Br
O O O
CH3CH2CH2C-H CH3CH2C-CH3 C
H
(p) CH3CH2CH2CH(CH3)CH2CONH2
70