专英第三章(有机化学)
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one another and are usually very similar in their properties, and so are difficult to separate.
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Optical isomers may arise when four different groups are bonded to one carbon atom, producing an asymmetric molecule. The property of having
70: heptaconta-
16: hexadeca-
26: hexacosa-
80: octaconta-
17: heptadeca-
27: heptacosa-
90: enneaconta-
18: octadeca-
28: octacosa-
19: nonadeca-
29: nonacosa-
❖
i-: iso-(异), implies a branched alkane with the
❖
second carbon in the end of chain linking
❖
with a methyl.
❖
neo-: (新), implies a branched alkane with the
polarized light(偏振光).
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Reactivity
The reactivity of saturated hydrocarbons is generally low, although hydrogen atoms are readily replaced by halogen atoms (halogenation). Double bonds or polar bonds provide sites where reaction is more likely to occur. Unsaturated hydrocarbons readily undergo addition reactions; aromatic compounds tend to undergo substitution reaction.
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表示取代基相对位置的字头：
iso- 异；
cis- 顺； trans- 反
neo- 新；
primary伯
o-（ortho-）邻； secondary仲 sec-
m-（meta-）间； tertiary叔 tert-
p-（para-）对； quaternary季
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conjugated double bonds(共轭双键).
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Aromatic hydrocarbons(芳烃) are unsaturated
compounds with planar ring systems stabilized by delocalized π bonding, as in benzene. Hydrocarbons that do not contain aromatic rings are termed
❖ CH4 methane; CH3—methyl甲基
❖ propane →propyl
butane →butyl;
❖ pentane →pentyl;
hexane →hexyl
❖ heptane →heptyl;
octane →octyl
❖ nonane →nonyl;
decane →decyl癸基
❖
second carbon at the end of chain linking
❖
with two methyls.
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❖E.G.
❖ C-C-C-C-C
C
❖ C-C-C-C
C
❖ C-C-C
C
n-pentane 正戊烷 isopentane 异戊烷 neopentane 新戊烷
optical isomers is called chirality(手性). A mixture of equal parts of the levorotatory(左旋) and dextrorotatory(右旋) isomers of a substance —— a racemic(外消旋) mixture— causes no net rotation of
1）Aliphatic Hydrocarbons（Fatty Hydrocarbons ，脂肪烃）
烷烃（alkane-paraffin hydrocarbons石蜡烃/烷属烃/链烷 烃CnH2n+2 ）命名数字头 + -ane
例:（以a结尾的数字头直接加-ne ）
甲烷: methane; 癸烷: decane; 庚烷: heptane;
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Isomerism
Pairs of molecules with the same molecular formula that rotate plane-polarized light in opposite
directions are called optical isomers(旋光异构) or enantiomers(对映异构). They are mirror images of
5-甲基-4-丙基壬烷 5-methyl-4-propylnonane
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CH2CH3 CH3CH2CH2CHCH2CHCH2CH2CH2CH3
六十烷: hexacontane 七十烷: heptacontane
八十烷: octacontane 九十烷: nonacontane
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❖ CnH2n+1 radicals (alkyls/hydrocarbyl)烃基的命
名： 将烃类名称的词尾 “ane” → “yl”
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支链烃类（hydrocarbon with branched chains）的命名：
i). 以最长的碳链为主链，从一端向另一端编号，使侧 链具有最低编号。如有几个侧链，按侧链取代基字头 的英文字母顺序排列。
例： CH3(CH2)3CHCH(CH2)2CH3 H3C CH2CH2CH：3
十三烷: tridecane
十四烷: tetradecane
十五烷: pentadecane 二十烷: (e)icosane
二十一烷: heneicosane 二十二烷: docosane
三十烷: triacontane 三十一烷: hentriacontane
四十烷: tetracontane 五十烷: pentacontane
31: hentriaconta-
12: dodeca-
22: docosa-
40: tetraconta-
13: trideca-
23: tricosa-
50: pentaconta-
14: tetradeca-
24: tetracosa-
60: hexaconta-
15:pentadeca-
25: pentacosa-
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Rotation of two carbon atoms joined by a double bond is inhibited by the π bond, and these two carbon atoms are similarly unable to rotate. In both cases, cis-trans isomerism is therefore possible. A carbon-carbon double bond creates a planar region in a molecule. The double bonds that alternate with single bonds are named as
戊: penta-
双, 两: di-,
己: hexa-
bi-, bis-
庚: hepta-
辛: octa-
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总碳数>10时：
一: hen(i)-;二: do-;三: tri(a)-;四: tetra-…
10. deca-
20: eicosa-
30: triaconta-
11: undeca, hendeca- 21: heneicosa-
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Some Introductory Concepts
A functional group is a chemically reactive atom or group of atoms that imparts characteristic properties to the family of organic compounds containing it. The site of reaction in an organic molecule is often a functional group, a multiple covalent bond, or a polar single bond. An electron-poor atom or group that will bond with an atom that has an available electron pair is called an electrophile. An electron-rich atom or group that will bond with an electron-deficient atom is called a nucleophile.
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1. Nomenclature of Hydrocarbons: （烃类命名法）
Number Prefix（数字前缀）：
总碳数≤10时
甲: meth-
壬: nona-
乙: eth-
癸: deca-
丙: prop-
半: hemi-, semi-
丁: buta-
单: mono-
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➢ Common nomenclature of alkanes
❖
First, described as above.
❖
Second, there are some rules:
❖
n-: normal(正), implies a straight-chain or
❖
unbranched alkane
Nomenclature of Organic Compounds
有机化合物的命名
Brief Introduction
Hydrocarbons
All organic compounds can be regarded as based on the structures of hydrocarbons. Saturated hydrocarbons contain only single covalent bonds; they may consist of straight or branched carbon chains (alkanes) or rings (cycloalkanes). All hydrocarbons with more than three carbon atoms exhibit structural isomerism. Groups containing one less hydrogen atom than an alkane are called alkyl groups. Unsaturated hydrocarbons are those containing double bonds (alkenes源自文库 or triple bonds (alkynes).
aliphatic(脂肪族) hydrocarbons. The preferred
system of nomenclature for organic compounds is that formulated by the International Union of Pure and Applied Chemistry, IUPAC.
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Optical isomers may arise when four different groups are bonded to one carbon atom, producing an asymmetric molecule. The property of having
70: heptaconta-
16: hexadeca-
26: hexacosa-
80: octaconta-
17: heptadeca-
27: heptacosa-
90: enneaconta-
18: octadeca-
28: octacosa-
19: nonadeca-
29: nonacosa-
❖
i-: iso-(异), implies a branched alkane with the
❖
second carbon in the end of chain linking
❖
with a methyl.
❖
neo-: (新), implies a branched alkane with the
polarized light(偏振光).
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Reactivity
The reactivity of saturated hydrocarbons is generally low, although hydrogen atoms are readily replaced by halogen atoms (halogenation). Double bonds or polar bonds provide sites where reaction is more likely to occur. Unsaturated hydrocarbons readily undergo addition reactions; aromatic compounds tend to undergo substitution reaction.
Company Logo
表示取代基相对位置的字头：
iso- 异；
cis- 顺； trans- 反
neo- 新；
primary伯
o-（ortho-）邻； secondary仲 sec-
m-（meta-）间； tertiary叔 tert-
p-（para-）对； quaternary季
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conjugated double bonds(共轭双键).
Company Logo
Aromatic hydrocarbons(芳烃) are unsaturated
compounds with planar ring systems stabilized by delocalized π bonding, as in benzene. Hydrocarbons that do not contain aromatic rings are termed
❖ CH4 methane; CH3—methyl甲基
❖ propane →propyl
butane →butyl;
❖ pentane →pentyl;
hexane →hexyl
❖ heptane →heptyl;
octane →octyl
❖ nonane →nonyl;
decane →decyl癸基
❖
second carbon at the end of chain linking
❖
with two methyls.
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❖E.G.
❖ C-C-C-C-C
C
❖ C-C-C-C
C
❖ C-C-C
C
n-pentane 正戊烷 isopentane 异戊烷 neopentane 新戊烷
optical isomers is called chirality(手性). A mixture of equal parts of the levorotatory(左旋) and dextrorotatory(右旋) isomers of a substance —— a racemic(外消旋) mixture— causes no net rotation of
1）Aliphatic Hydrocarbons（Fatty Hydrocarbons ，脂肪烃）
烷烃（alkane-paraffin hydrocarbons石蜡烃/烷属烃/链烷 烃CnH2n+2 ）命名数字头 + -ane
例:（以a结尾的数字头直接加-ne ）
甲烷: methane; 癸烷: decane; 庚烷: heptane;
Company Logo
Isomerism
Pairs of molecules with the same molecular formula that rotate plane-polarized light in opposite
directions are called optical isomers(旋光异构) or enantiomers(对映异构). They are mirror images of
5-甲基-4-丙基壬烷 5-methyl-4-propylnonane
Company Logo
CH2CH3 CH3CH2CH2CHCH2CHCH2CH2CH2CH3
六十烷: hexacontane 七十烷: heptacontane
八十烷: octacontane 九十烷: nonacontane
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❖ CnH2n+1 radicals (alkyls/hydrocarbyl)烃基的命
名： 将烃类名称的词尾 “ane” → “yl”
Company Logo
支链烃类（hydrocarbon with branched chains）的命名：
i). 以最长的碳链为主链，从一端向另一端编号，使侧 链具有最低编号。如有几个侧链，按侧链取代基字头 的英文字母顺序排列。
例： CH3(CH2)3CHCH(CH2)2CH3 H3C CH2CH2CH：3
十三烷: tridecane
十四烷: tetradecane
十五烷: pentadecane 二十烷: (e)icosane
二十一烷: heneicosane 二十二烷: docosane
三十烷: triacontane 三十一烷: hentriacontane
四十烷: tetracontane 五十烷: pentacontane
31: hentriaconta-
12: dodeca-
22: docosa-
40: tetraconta-
13: trideca-
23: tricosa-
50: pentaconta-
14: tetradeca-
24: tetracosa-
60: hexaconta-
15:pentadeca-
25: pentacosa-
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Rotation of two carbon atoms joined by a double bond is inhibited by the π bond, and these two carbon atoms are similarly unable to rotate. In both cases, cis-trans isomerism is therefore possible. A carbon-carbon double bond creates a planar region in a molecule. The double bonds that alternate with single bonds are named as
戊: penta-
双, 两: di-,
己: hexa-
bi-, bis-
庚: hepta-
辛: octa-
Company Logo
总碳数>10时：
一: hen(i)-;二: do-;三: tri(a)-;四: tetra-…
10. deca-
20: eicosa-
30: triaconta-
11: undeca, hendeca- 21: heneicosa-
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Some Introductory Concepts
A functional group is a chemically reactive atom or group of atoms that imparts characteristic properties to the family of organic compounds containing it. The site of reaction in an organic molecule is often a functional group, a multiple covalent bond, or a polar single bond. An electron-poor atom or group that will bond with an atom that has an available electron pair is called an electrophile. An electron-rich atom or group that will bond with an electron-deficient atom is called a nucleophile.
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1. Nomenclature of Hydrocarbons: （烃类命名法）
Number Prefix（数字前缀）：
总碳数≤10时
甲: meth-
壬: nona-
乙: eth-
癸: deca-
丙: prop-
半: hemi-, semi-
丁: buta-
单: mono-
Company Logo
➢ Common nomenclature of alkanes
❖
First, described as above.
❖
Second, there are some rules:
❖
n-: normal(正), implies a straight-chain or
❖
unbranched alkane
Nomenclature of Organic Compounds
有机化合物的命名
Brief Introduction
Hydrocarbons
All organic compounds can be regarded as based on the structures of hydrocarbons. Saturated hydrocarbons contain only single covalent bonds; they may consist of straight or branched carbon chains (alkanes) or rings (cycloalkanes). All hydrocarbons with more than three carbon atoms exhibit structural isomerism. Groups containing one less hydrogen atom than an alkane are called alkyl groups. Unsaturated hydrocarbons are those containing double bonds (alkenes源自文库 or triple bonds (alkynes).
aliphatic(脂肪族) hydrocarbons. The preferred
system of nomenclature for organic compounds is that formulated by the International Union of Pure and Applied Chemistry, IUPAC.