厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）第四章 烷烃 命名 构象分析及合成导论（4.4-4.7）Physical Properties of Alkanes and Cycloalkanes

ORGANIC CHEMISTRY Chapter 4 4.4 Nomenclature of Cycloalkanes Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 4.4 Nomenclature of Cycloalkanes

ORGANIC CHEMISTRY Chapter 4 4. 4a Monocyclic Compounds o Cycloalkanes with only one ring are named by attaching the prefix cyclo-to the names of the alkanes possessing the same number of carbon atoms △ Cyclopropane Cyclopentane Cyclohexane 环丙烷 环戊烷 环己烷 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 4.4A Monocyclic Compounds Cycloalkanes with only one ring are named by attaching the prefix cyclo- to the names of the alkanes possessing the same number of carbon atoms. Cyclopropane Cyclopentane Cyclohexane 环丙烷 环戊烷 环己烷

ORGANIC CHEMISTRY Chapter 4 CH CH,CH CH HOcH Br Br 4-Bromo-2-ethyl-l-methylcyclohexane 1-Bromo-3-ethy l-5-methylcyclohexane 1-甲基2-乙基-4-溴环己烷 1-甲基-3-乙基-5-溴环己烷 OH C 2-Chlorocyclohexanol 2-氯环己醇 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 4-Bromo-2-ethyl-1-methylcyclohexane CH3 CH2CH3 Br 1-甲基-2-乙基-4-溴环己烷 CH2CH3 Br CH3 1-Bromo-3-ethyl-5-methylcyclohexane 1-甲基-3-乙基-5-溴环己烷 OH Cl 2-Chlorocyclohexanol 2-氯环己醇

ORGANIC CHEMISTRY Chapter 4 When a single ring system is attached to a single chain with a greater number of carbon atoms, or when more one ring system is attached to a single chain, then it 1s appropriate to name the compounds as cycloalkylalkanes CHoCHoCHoCH yclopropylbutane 1, 3-Dicyclohexylpropane 1-环丙基丁烷 ,3-二环己基丙烷 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 When a single ring system is attached to a single chain with a greater number of carbon atoms, or when more one ring system is attached to a single chain, then it is appropriate to name the compounds as cycloalkylalkanes. CH2CH2CH2CH3 1-Cyclopropylbutane 1,3-Dicyclohexylpropane 1-环丙基丁烷 1,3-二环己基丙烷

ORGANIC CHEMISTRY Chapter 4 4.4 b Bridged Hydrocarbons(桥环烃) (a) Bicyclic Compounds o Compounds containing two fused or bridged rings- cycloalkanes Bridgehead One-carbon bridge Bridgehead Bicyclo 2. 2. I heptane Two-carbon bridge 二环22.庚烷 Parent name: the total number of carbon atoms in the rings Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 4.4B Bridged Hydrocarbons (桥环烃) (a) Bicyclic Compounds Compounds containing two fused or bridged rings — bicycloalkanes Bridgehead Bridgehead Bridgehead Bridgehead One-carbon bridge One-carbon bridge Bicyclo[2.2.1]heptane Two-carbon bridge Two-carbon bridge 二环[2.2.1]庚烷 Parent name: the total number of carbon atoms in the rings

ORGANIC CHEMISTRY Chapter 4 CH3 CH3 4 CH2CH3 CH,CH 7,7-二甲基-2-乙基二环22.1庚烷 2-Ethyl-7, 7-dimethylbicyclo[2.2.1 heptane 4 Bicyclo 5.2.0]nonane 二环520]壬烷 6 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 CH3 CH3 CH2CH3 1 CH2CH3 2 3 4 5 6 7 7,7-二甲基-2-乙基二环[2.2.1]庚烷 2-Ethyl-7,7-dimethylbicyclo[2.2.1]heptane 1 2 3 4 5 6 7 8 9 Bicyclo[5.2.0]nonane 二环[5.2.0]壬烷

ORGANIC CHEMISTRY Chapter 4 (b) polycyclic Compounds o Compounds consisting of three or more rings may be named by adding the appropriate prefix tricyclo- tetracyclo-, etc. before the name of the open-chain hydrocarbon o a polycyclic system is regarded as containing a number of rings equal to the number of scissions required to convert the system into an open-chain compound 三环32.1.024辛烷 2 Tricyclo 3. 2.1.0- octane Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 (b) Polycyclic Compounds Compounds consisting of three or more rings may be named by adding the appropriate prefix "tricyclo-", "tetracyclo-", etc. before the name of the open-chain hydrocarbon. A polycyclic system is regarded as containing a number of rings equal to the number of scissions required to convert the system into an open-chain compound. 2 3 4 1 5 6 7 8 三环[3.2.1.02,4]辛烷 Tricyclo[3.2.1.02,4]octane

ORGANIC CHEMISTRY Chapter 4 4 Spiro hydrocarbons(螺环烃) A spiro atom o a spiro union" is one formed by a single atom which is the only common member of two rings o The common atom is designated as the spiro atom o According to the number of spiro atoms present, the compounds are distinguished as monospiro- dispiro-, trispirocompounds, etc Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 4.4C Spiro Hydrocarbons (螺环烃) A spiro atom A "spiro union" is one formed by a single atom which is the only common member of two rings. The common atom is designated as the "spiro atom". According to the number of spiro atoms present, the compounds are distinguished as monospiro-, dispiro-, trispirocompounds, etc

ORGANIC CHEMISTRY Chapter 4 o Monospiro compounds consisting of only two alicyclic rings as components are named by placing"spiro"before the name of the normal acyclic hydrocarbon of the same total number of carbon atoms g The number of carbon atoms linked to the spiro atom in each ring is indicated in ascending order in brackets placed between the spiro prefix and the hydrocarbon name 9 The carbon atoms in monospiro hydrocarbons are numbered consecutively starting with a ring atom next to the spiro atom, first through the smaller ring(if such be present)and then through the spiro atom and around the second ring Cl 104 3 螺34]辛烷6氯螺[4.5]癸烷 Spiro[3. octane 6-Chlorospiro[4.5 ]decane Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 Monospiro compounds consisting of only two alicyclic rings as components are named by placing "spiro" before the name of the normal acyclic hydrocarbon of the same total number of carbon atoms. The number of carbon atoms linked to the spiro atom in each ring is indicated in ascending order in brackets placed between the spiro prefix and the hydrocarbon name. The carbon atoms in monospiro hydrocarbons are numbered consecutively starting with a ring atom next to the spiro atom, first through the smaller ring (if such be present) and then through the spiro atom and around the second ring. Cl 螺[3.4]辛烷 Spiro[3.4]octane 6-Chlorospiro[4.5]decane 6 氯螺[4.5]癸烷 1 2 3 3 1 2 4 5 5 6 7 8 9 10 6 7 8 4

ORGANIC CHEMISTRY Chapter 4 4.5 Nomenclature of alkenes and Cycloalkenes Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 4 4.5 Nomenclature of Alkenes and Cycloalkenes