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Organic chemistry B Chapter 13 Ali phatic cyclic compounds Alicyclic compounds By Prof. Dr. Adel M. Awadallah Islamic

Organic chemistry B Chapter 13 Ali phatic cyclic compounds Alicyclic compounds By Prof. Dr. Adel M. Awadallah Islamic University of Gaza. Cycloalkanes: Nomenclature. Industrial source. Preparation. Reactions similar to that of alkanes (free radical substitution) , .

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Organic chemistry B Chapter 13 Ali phatic cyclic compounds Alicyclic compounds By Prof. Dr. Adel M. Awadallah Islamic

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  1. Organic chemistry B Chapter 13 Aliphatic cyclic compounds Alicyclic compounds By Prof. Dr. Adel M. Awadallah Islamic University of Gaza

  2. Cycloalkanes: Nomenclature

  3. Industrial source

  4. Preparation

  5. Reactionssimilar to that of alkanes (free radical substitution) ,

  6. Reactionsalkenes (addition or cleavage of the double bond)

  7. Ring Strain in Cyclopropane • Average heat of composition per CH2 = 157.4 Kcal / mol • Ring strain in cyclopropane = 27.6 Kcal/mol • Ring strain in cyclobutane = 26.3 Kcal/mol

  8. Ring Strain in Cyclopropane • Eclipsing (torsional) strain: • Strain resulting from deviation from the staggered arrangement • Bond-Angle Strain: • Strain resulting from deviation from the normal bond angle (tetrahedral 109.5)

  9. Addition to cyclopropane

  10. Addition to cyclopropaneCyclobutane undergoes hydrogenation under vigorous conditions

  11. Relieve of torsional strain in cyclobutanePuckered structure (butterfly)

  12. Relieve of torsional strain in cyclopentaneEnvelope (half chair) structure

  13. Conformations of Cyclohexane

  14. Conformations of cyclohexane

  15. Twist boat is more stable than the boat conformation

  16. 1,2 + 1,4 Trans diaxial or diequatorial1,3 cis diaxial or diequatorial

  17. Example

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