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CHAPTER 4 - 4 Organic Compounds Cycloalkanes and their...

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4. Organic Compounds: Cycloalkanes and their Stereochemistry Based on McMurry’s Organic Chemistry , 7 th edition
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2 ± We’ve discussed open-chained compounds up to this point ± Many organic compounds contain rings of carbon atoms e.g. - Prostaglandins - Steroids
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3 Why this chapter? ± Because cyclic molecules are commonly encountered in all classes of biomolecules : - Proteins - Lipids - Carbohydrates - Nucleic acids
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4 4.1 Naming Cycloalkanes ± Cycloalkanes are saturated cyclic hydrocarbons ± Have the general formula (C n H 2n )
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5 Naming Cycloalkanes 1. Find the parent (# of carbons in the ring) 2. Number the substituents and write the name Work Problems 4.1 and 4.2 here
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6 4.2 Cis-Trans Isomerism in Cycloalkanes ± Cycloalkanes are less flexible than open-chain alkanes ± Much less conformational freedom in cycloalkanes
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7 ± Because of their cyclic structure, cycloalkanes have 2 faces as viewed edge-on “top” face “bottom” face - Therefore, isomerism is possible in substituted cycloalkanes - There are two different 1,2-dimethylcyclopropane isomers cis – on the same side trans on the opposite side (across)
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8 Stereoisomers ± Compounds which have their atoms connected in the same order but differ in 3-D orientation are called stereoisomers . cis -1,2-dimethylcyclopropane trans -1,2-dimethylcyclopropane Work Problems 4.4 and 4.5 here
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9 4.3 Stability of Cycloalkanes: Ring Strain ± Rings larger than 3 atoms are not flat ± Cyclic molecules can assume nonplanar conformations to minimize angle strain and torsional strain by ring-puckering ± Larger rings have many more possible conformations than smaller rings and are more difficult to analyze
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10 Stability of Cycloalkanes: The Baeyer Strain Theory
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CHAPTER 4 - 4 Organic Compounds Cycloalkanes and their...

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