Solutions_Manual_for_Organic_Chemistry_6th_Ed 56

Solutions_Manual_for_Organic_Chemistry_6th_Ed 56 - 3- 1 1 -

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Unformatted text preview: 3- 1 1 - -----------------------., -1 5-------------------------.0 kJ/mole : ( 3.6 kcal/mole) 0° %��l e c lipsed 1 x H H 4 .2 kJ/mole + 2 H-H � 60° 1 20 ° dihedral angle 8 H CH3 H staggered x 5 .4 kJ/mole H-CH3 = 1 5 .0 kJ/mole ( 3 . 6 kcaI/mole) %��l eclipsed 3-1 2 0° 42H H &: H 5 e ,, 1 2. 1 80° 240° ec lipsed 5 HC .H 3 4 H 54 H H3 C H �2 'fJ H CH3 s taggered H3 H3C H � & H e ,, 300° 1 2.5 1 e cli psed J!I. 2 4 3.8 4. 2 � , 3.8 dihedral 360° angle 8 A l l energy values are per mole . 5 H3 C 1 2. CH3 e cli psed 5 ifH 3 .4 (Note that the lowest energy conformers at 60° and 1 80° have at l east one CH3-CH3 i nteraction = 3 .8 kJ (0.9 kcal) higher than ethane.) 'fJ H H H3C � CH3 H 'fJ H CH3 H s taggered CH3 s taggered Relative energies on the graph above were calculated using these values from the text: 3 .8 kJ/mole (0.9 kcaI/mole) for a CHrCH3 g auche (staggered) interaction ; 4 . 2 kJ/mole (l.0 kcaI/mole) for a H-H e c l ipsed i nteraction ; 5 .4 kJ/mole ( 1 . 3 kcaI/mole) for a H -CH} e clipsed interaction; 1 2.5 kJ/mole (3 . 0 kcaI/mole) for a CHrCH} e cli psed interaction . These values in kJ/mole are noted on each structure and are summed to give the energy value on the graph . S l i gh t variation between thi s graph and t h e one i n the text are due t o rounding. 47 ...
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