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Chapter 2

Chapter 2. Strain and Stability. CH 3 CH 2 -H 98.2. H 2 C=CH-H 110. HC C-H 132. H 3 C-H 105.1. CH 3 CH 2 -H 98.2. (CH 3 ) 2 CH-H 95.1. (CH 3 ) 3 C-H 93.2. 94.5. 82.3. 71.1. H 3 C-CH 3 90.4. H 2 C=CH 2 174.1. HC CH 230.7. CH 3 -F 109.9. CH 3 -Cl 84.6. CH 3 -Br 70.9.

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Chapter 2

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  1. Chapter 2 Strain and Stability

  2. CH3CH2-H 98.2 H2C=CH-H 110 HCC-H 132 H3C-H 105.1 CH3CH2-H 98.2 (CH3)2CH-H 95.1 (CH3)3C-H 93.2 94.5 82.3 71.1 H3C-CH3 90.4 H2C=CH2 174.1 HCCH 230.7 CH3-F 109.9 CH3-Cl 84.6 CH3-Br 70.9 CH3-I 57.2 CH3-OH 92.3 CH3-NH2 84.9 BDE

  3. Heats of Formation for Alkanes

  4. Group Increments

  5. Strain Energy in Cycloalkanes

  6. CH3CH2-H 98.2 H2C=CH-H 110 HCC-H 132 H3C-H 105.1 CH3CH2-H 98.2 (CH3)2CH-H 95.1 (CH3)3C-H 93.2 Radical Stability

  7. +CH3 312 CH3CH2+ 273 (CH3)2CH+ 246 (CH3)3C+ 231 CH3CH2+ 273 H2C=CH+ 287 287 H2NCH2+ 218 HOCH2+ 243 FCH2+ 290 NCCH2+ 318 Carbocation Stability

  8. Carbanion Stability CH3CH2-H 50 (CH3)3C-H 71 H2C=CH-H 44 HCC-H 24

  9. Conformational Analysis-Ethane

  10. Conformational Analysis-Butane

  11. g+g– Pentane Interaction

  12. Cycloalkane Conformations (3-5)

  13. Cyclohexane Conformations

  14. A Values

  15. Medium Rings Medium Rings Cycloalkanes (CnH2n) Strain Energies Small Ring Common Rings Large Rings

  16. Transannular Strain in Cyclodecane

  17. Polycyclic Systems

  18. trans-cyclooctene trans-Cycloalkenes trans-cycloheptane

  19. Bicyclooctenes

  20. A values in heterocycles

  21. Donor-Acceptor Ability Donor lone pair > bonding pair C:– > N: > O: (p) > O: (sp2) > F: I: > Br: > Cl: > F: C-H > N-H > O-H > F-H C-I > C-Br > C-Cl > C-F C-S > C-C > C-N > C-O > C-F Acceptor C-F > C-O > C-N > C-C C-I > C-Br > C-Cl > C-F C-S > C-O C-P > C-N

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