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Foundations of Organic Chemistry - Dr Jacksons Home Page：有机化学基础-杰克逊博士的主页
Cycloalkanes Organic Chem I: lecture 9 by Doba Jackson, Ph.D. Lecture Alkanes Naming alkanes con’t Newman projections con’t Cycloalkanes Naming cycloalkanes Cis-Trans isomerism Cyclopropane Cyclobutane Introduction to Cycloalkanes Cycloalkanes, common names Naming Cycloalkanes Step 1: Find the Parent If the ring has equal or more carbons, it is the parent. Step 2: Number the substituents with the lowest numbers and write the name. Substituents should have the lowest possible numbers When two or more substituents can have the same number, they are numbered by alphabetical priority When two or more substituents can have the same number, they are numbered by alphabetical priority Some Examples Problem 4.13: Draw two conformations of trans 1,4 dimethylcyclohexane Methyl groups are on opposite faces of the ring One trans conformation has both methyl groups equatorial and only a gauche interaction between methyls (3.8 kJ/mol). Steric strain of 15.2 kJ/mol makes the diaxial conformation 11.4 kJ/mol less favorable than the diequatorial conformation trans-1,2-dimethylcyclohexane will exist almost exclusively (99%) in the diequatorial conformation Trans-1,2-Dimethylcyclohexane Conformations of Polycyclic Molecules Decalin consists of two cyclohexane rings joined to share two carbon atoms and a common bond. Two isomeric forms of decalin: trans fused or cis fused In cis-decalin hydrogen atoms at the bridgehead carbons are on the same face of the rings In trans-decalin, the bridgehead hydrogens are on opposite faces Flips and rotations do not interconvert cis and trans * * * * * * * * * * * * * * * * Problem 3.1- Give IUPAC names for the following compounds 1,4 dimethyl cyclohexane 1-methyl 3-propyl cyclopentane 3-cyclobutyl pentane 1-bromo 4-ethyl cyclodecane 1-isopropyl 2-methyl cyclohexane or 1-(1-methylethyl) 2-methyl cyclohexane 4-bromo 2-methyl 1-tert-butyl cycloheptane Stability of Cycloalkanes: Ring Strain Rings larger than 3 atoms are not flat Cycl
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