lecture 04 - 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 Most 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 Find the parent. # of carbons in the ring. Number the substituents
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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-dimethyl-cyclopropane isomers
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8 Stereoisomerism Compounds which have their atoms connected in the same order but differ in 3-D orientation
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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 Baeyer (1885): since carbon prefers to have bond angles of approximately 109°, ring sizes other than five and six may be too strained to exist
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