Answer Happy

Assigning a value to aromate station is actually Consider a hypothetical reaction in which a molecule of hydrogen is added to benene to yield 1 cyclohexadene Nest consideranalogous hydrogenation reactions of 13-cyclohexadienseading to cych and of cyclohexene leading to cycan Part A +H + +25 kamol -109 kimol -117 kmal Cydonde Con Optic tactures of benzene, 1.1, 1.2 dyret mot Evoke the courgy of the following action in the new logo of rage of standard we 1 On the basis of hydrogations, would you condus toote some sort or empty on you atch the words in the left column to the appropriate blanks in the sentences on the right Addition of H, to benzentrades an H H bood and a bond for two C H bonds. Undoing destroys the Incontri adation to other 1.3 cyclohexadione or cyclohexenet the same bonds but does not result in any loss of aromaticity there is nothing to lose). Therefore, the difference in the heat of hydrogenation (134 k moleforenced to 1.3-cyclohexadienend 142. mol! referenced 10 cyclohexene) is more of the cromaticity of Benson Reliable quonstative comparisons require more experimental daca theats of formation. There we generally be valable only for very simple molecules and will most never be valable for boven Sompounds. As a caso in point, consider to what extent on the 10 cincin molecule 1,6 methanocyclodeco1.3.5.7.0-pontoneridged naphthone') is stabilized by aromaticity. Evidence provided by the way crystal structure suggests a fut delocal system. The two that make up the base we very nearly coplanar al bonds intermediate in longth between mange and double in agosto they are in naphther 118 11 1.42 1.41 According of hydin en more woman The mu For stave 112 1.0 1.40 de surowie mo Calculations provide a viable alternative to experiment for the chemical dalis. Although we hydrogenation energies may be out to ration enorme GLAV

Optimize the structures of benzene, 1,3-cyclohexadione, naphthalone, and 1,2-dihydronaphthalene using the HF/6-316' model Evaluate the energy of the following reaction, relating the energy of hydrogenation of naphthalene to that of benzene (as a standard) Naphthalene 3-cydohexadiene 1,2-hydronaphthalene Benaene On the basis of relative hydrogenation energies, would you conclude that naphthalene is stabilized (by aromaticity) to about the same extent as is benzene or to a lesser or greater extent? Try to explain your result Match the words in the left column to the appropriate blanks in the sentences on the right Reset Help 53 kJ. mol 112 kl. mol According to HF/8-31G calculations, the energy of hydrogenation of naphthalene relative to that of benzene is more aromatic This implies that naphthalene is by this particular than benzene by For reference calculations suggest a value of 134 kJ - mol-' for the aromatic stabilization of benzene. measure 112 kJ. mol less aromatic 53 11 mol1