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Cycloalkanes

Cycloalkanes. Cycloalkanes. Compounds that contain rings of carbon atoms Have the general formula C n H 2n Represented by polygons in skeletal drawings. cyclopropane cyclobutane cyclopentane. Naming cycloalkanes.

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Cycloalkanes

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  1. Cycloalkanes

  2. Cycloalkanes • Compounds that contain rings of carbon atoms • Have the general formula CnH2n • Represented by polygons in skeletal drawings cyclopropane cyclobutane cyclopentane

  3. Naming cycloalkanes • Count the number of carbon atoms in the ring and the number in the largest substituent. • If the number of carbon atoms in the ring is equal to or greater than the number in the largest substituent, the compound is named as alkyl-substituted cycloalkane.

  4. Substituted cycloalkane Cycloalkyl-substituted alkane Methylcyclopentane 3 carbons 4 carbons 1-cyclopropylbutane

  5. 2. For alkyl-substituted cycloalkanes, start at a point of attachment and number the substituents on the ring so as to arrive at the lowest sum. • 2 1 • 3 6 • 4 5 • 6 1 • 5 2 • 4 3 1,3-dimethylcyclohexane NOT 1,5-dimethylcyclohexane

  6. CH3 CH2CH3 • When two or more different alkyl groups or halogens are present, number them by alphabetical priority. 1-ethyl-2-methylcyclopentane NOT 2-ethyl-1-methylcyclopentane

  7. Cis-trans isomers • Because there is not free rotation in cycloalkanes, geometric isomers called stereoisomers are formed. • Cis (L. “on the same side”) • Trans (L. “across from”) • Geometric isomers do not convert back and forth.

  8. H H H H H Cl H H Cl H H H H H Cl H H Cl H H H H H H trans-1,4-dichlorocyclohexane cis-1,4-dichlorocyclohexane

  9. Chair Conformation

  10. Homework Page 320: 39-43

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