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Understanding Cyclic Alkanes and Isomerism in Organic Chemistry

Dive into the world of cyclic alkanes, from cyclopropane to common organics like nicotine and cholesterol. Learn how to name cyclic alkanes with one substituent and explore their isomerism. Discover the sources, physical properties, and chemical properties of alkanes.

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Understanding Cyclic Alkanes and Isomerism in Organic Chemistry

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  1. 1.12 CYCLIC ALKANES cyclopropane cyclopentane cyclobutane

  2. MORE CYCLOALKANES ( cyclo = ring ) cyclopentane MOST STABLE cyclohexane

  3. COMMON ORGANICS THAT CONTAIN RINGS nicotine cholesterol mescaline caffeine

  4. 1.13 Naming cyclic alkanes

  5. RINGS WITH ONE SUBSTITUENT sec-butylcyclohexane No locant is needed. With one substituent on a ring , it is automatically on carbon 1.

  6. C H 3 C H 3 C H 3 C H C H 3 3 C H 3 C H 3 C H C H 3 2 C H C H 2 3 SOME CYCLOALKANES 1,3-dimethylcyclopentane Drawn differently but same name. 2 1 = 3 Begin numbering the ring at one of the attached groups, so that the attached groups have the lowest numbers. 4 3 1 2 2 1 3 3-ethyl-1,1-dimethylcyclobutane 1-ethyl-4-methylcyclohexane The more substituted carbon takes precedence even though E comes before M. E before M

  7. NAMES OF THE COMMON ALKYL GROUPS ARE ALSO USEFUL WITH CYCLIC COMPOUNDS isopropylcyclohexane C H C H 3 C H 3 2-cyclohexylpropane C H 3 C C H 3 C H 3 • tert-butylcyclopentane You can base the name on either the RING or the LONGEST CHAIN 2-cyclopentyl-2-methylpropane

  8. Name This 1-isopropyl-2-methylcyclohexane

  9. 1.14 Isomerism in cyclic alkanes • Constitutional isomerism • Stereoisomerism

  10. C H 3 C H 3 Constitutional Isomers of C7H14 C H C H 3 3 C H 3 1,3-dimethylcyclopentane 1,1-dimethylcyclopentane C H 3 1,2-dimethylcyclopentane

  11. More constitutional isomers of C7H14 CAN YOU THINK OF ANY MORE?

  12. Stereoismerism in cyclic alkanes 1. Occurs in cyclic alkanes with two or more groups attached to the ring. 2. Attached groups do not have to be the same. 3. Attached groups must be on different carbon atoms. 4. The stereoisomers are named “cis” and “trans”

  13. Stereoismerism in cyclic alkanes (cont) We will only consider the stereoisomerism in rings with two attached groups. 1. cis:the groups are on the same side of the ring (above or below)

  14. Stereoismerism in cyclic alkanes (cont) 2. trans : the groups are on opposite sides of the ring (one group above and one group below)

  15. C H 3 C H 3 C H 3 C H 3 C H 3 C H 3 C H 3 C H 3 Stereoisomers of 1,3–dimethylcyclopetane cis-1,3-dimethylcyclopentane trans-1,3-dimethylcyclopentane cis-1,3-dimethylcyclopentane trans-1,3-dimethylcyclopentane

  16. C H 3 C H 3 C H 3 C H 3 C C C C H H H H 3 3 3 3 Stereoisomers of 1,2–dimethylcyclopentane cis-1,2-dimethylcyclopentane trans-1,2-dimethylcyclopentane cis-1,2-dimethylcyclopentane trans-1,2-dimethylcyclopentane

  17. C H 3 C H 3 1,1-dimethylcyclopentane Neither cis nor trans Attached groups must be on different carbon atoms

  18. 1.15 Sources of alkanes

  19. 1.16 Physical properties of alkanes • Water solubility • B.P. and M.P • Branched • Linear • Cyclo • Increasing M.W.

  20. 1.17 Chemical Properties • Combustion…… • Energy source • CO2 and H2O are products • Write balanced equations

  21. THE END

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