西北农林科技大学：《有机化学 Organic chemistry》课程PPT教学课件（2017）McMurry OCB 3Ed Chapter 04 Organic compounds cycloalkanes and their stereochemistry

Organic Chemistry with BiologicalApplications,3rEdition John McMurry Chapter 04 Organic compounds: cycloalkanes and their stereochemistry The chemistry of a given functional group is affected by being in a ring rather than an open chain. Cyclic molecules are so commonly encountered in most pharmaceuticals and in all classes of biomolecules. It's important to understand the consequences of cyclic structures

Chapter 04 Organic compounds ： cycloalkanes and their stereochemistry Organic Chemistry with Biological Applications, 3 rd Edition John McMurry The chemistry of a given functional group is affected by being in a ring rather than an open chain. Cyclic molecules are so commonly encountered in most pharmaceuticals and in all classes of biomolecules. It’s important to understand the consequences of cyclic structures

有额化学 Organic Chemistry with BiologicalApplications,3 Edition John McMurry Chapter 04 Organic compounds: cycloalkanes and their stereochemistry Homework:P86d:3.42a,b; P108:4.18a-d Key Notes Conformation;Stability;Ring Strainj Stereochemistry;a ee bonds

Chapter 04 Organic compounds ： cycloalkanes and their stereochemistry Organic Chemistry with Biological Applications, 3 rd Edition John McMurry Homework： P86d:3.42a,b; P108: 4.18a-d Key Notes Conformation; Stability; Ring Strain; Stereochemistry ; a & e bonds

Main Contents INaming alkanes of Bridged and spiro rings Conformations of cycloalkanes a &e bonds in cyclohexane Effects of alkyl groups on conformation Conformations of polvcvclic molecules A membrane channel protein that conducts Cl2 ions across cell membranes

Main Contents ◼Naming alkanes of Bridged and spiro rings ◼Conformations of cycloalkanes ◼ a & e bonds in cyclohexane ◼Effects of alkyl groups on conformation ◼Conformations of polycyclic molecules A membrane channel protein that conducts Cl2 ions across cell membranes

Sec 1 Naming alkanes of Bridged and spiro rings -Rings of carbon atoms (-CH2-groups) -Formula:CnH2n -Nonpolar,insoluble in water -Compact shape -Melting and boiling points similar to branched alkanes with same number of carbons

Sec 1 Naming alkanes of Bridged and spiro rings ▪Rings of carbon atoms (-CH2 - groups) ▪Formula: CnH2n ▪Nonpolar, insoluble in water ▪Compact shape ▪Melting and boiling points similar to branched alkanes with same number of carbons

Naming the following cycloalkanes. 1,1,2-trimethycyclohexane CH CH2CH 4-cyclopentyl-2,3-dimethylhexane trans-1-ethyl-2-methylcyclohexane 1,2-dicyclopropylethane ■Cycloalkane usually base compound。 Number carbons in ring if >1 substituent. First in alphabet gets lowest number. May be cycloalkyl attachment to chain

CH3 1 CH2CH3 2 trans-1-ethyl-2-methylcyclohexane 1,1,2-trimethycyclohexane 1,2-dicyclopropylethane 4-cyclopentyl-2,3-dimethylhexane ◼Cycloalkane usually base compound。 ◼Number carbons in ring if >1 substituent. ◼First in alphabet gets lowest number. ◼May be cycloalkyl attachment to chain. Naming the following cycloalkanes

Additional Ring Systems polycyclics-molecules containing more than one ring spirocyclics one carbon atom is common to two rings bridged and fused polycyclics two or more atoms are common to more than one ring

Additional Ring Systems polycyclics - molecules containing more than one ring spirocyclics - one carbon atom is common to two rings bridged and fused polycyclics - two or more atoms are common to more than one ring

桥环与螺环的命名 3 8 螺4.5]癸烷 4-甲基-螺2.4]庚烷 spiro[3.7]undecane

螺[4.5]癸烷 6 5 4 3 2 1 CH3 10 9 8 6 7 5 3 4 2 1 4-甲基-螺[2.4]庚烷 桥环与螺环的命名 spiro[3.7]undecane

Bicyclic Alkanes Fused rings(稠环)share two adjacent carbons. Bridged rings(桥环)share two nonadjacent C's. bicyclo[3.1.0]hexane bicyclo[2.2.1]heptane

Bicyclic Alkanes ▪Fused rings（稠环）share two adjacent carbons. ▪Bridged rings（桥环）share two nonadjacent C’s. bicyclo[3.1.0]hexane bicyclo[3.1.0]hexane bicyclo[2.2.1]heptane bicyclo[2.2.1]heptane

Polycyclic Rings Bicycloalkanes: bicyclo[x.y.z]alkane(x≥y≥z) numbering starts at a bridgehead,proceeds around the largest bridge first,then around successively smaller bridges bicyclo[4.4.0]decane 二环[4.4.0]癸烷（十氢化萘) bicyclo[2.2.1.]heptane bicyclo[4.1.0]heptane bicyclo[3.2.1]octane

bicyclo[4.4.0]decane bicyclo[2.2.1.]heptane bicyclo[4.1.0]heptane bicyclo[3.2.1]octane 二环[4.4.0]癸烷（十氢化萘） Bicycloalkanes: bicyclo[x.y.z]alkane (x  y  z) numbering starts at a bridgehead, proceeds around the largest bridge first, then around successively smaller bridges C C Cz Cy Cx Polycyclic Rings

Polycyclic Rings 3 6 6 2,7,7-三甲基二环 三环2.2.1.02,61庚烷 [2.2.1]庚烷 三环[3.3.1.137]癸烷 (金钢烷)

2,7,7-三甲基二环 [2.2.1]庚烷 7 6 5 4 3 2 1 三环[3.3.1.13、7]癸烷 (金钢烷) 9 8 7 6 5 4 3 2 1 7 6 5 4 3 2 1 三环[ 2.2.1.02,6]庚烷 三环[3.3.1.13、7]癸烷 (金钢烷) 三环[ 2.2.1.02,6 2,7,7-三甲基二环 ]庚烷 [2.2.1]庚烷 三环[3.3.1.13、7]癸烷 (金钢烷) 三环[ 2.2.1.02,6]庚烷 三环[3.3.1.13、7]癸烷 (金钢烷) 三环[ 2.2.1.02,6 2,7,7-三甲基二环 ]庚烷 [2.2.1]庚烷 三环[3.3.1.13、7]癸烷 (金钢烷) 三环[ 2.2.1.02,6]庚烷 Polycyclic Rings