Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Construct MO energy diagrams for the cyclopropenyl cation, radical, and anion. Which of these species is aromatic according to the Hückel criteria?
Pyrene has been determined experimentally to be aromatic. At first glance, however, its structure appears to break Hückel’s rule. How so? Can you explain why pyrene exhibits aromaticity?Hint: What are the characteristics of the π system on the periphery of the molecule?
Imagine that you used isoprene as diene – in that case you don’t have to worry about assigning endo vs exo. Draw the "endo" and "exo" products of the Diels-Alder reaction between isoprene and maleic anhydride, and explain why the distinction is irrelevant here.
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- Use the inscribed polygon method to show the pattern of molecularorbitals in cyclooctatetraene. Indicate the arrangement of electrons in these orbitals forcyclooctatetraene, and explain why cyclooctatetraene is not aromatic.arrow_forwardCan someone draw the arrows for this reaction so I can understand how the product was formed? I'm having trouble understanding that aspect of the Diels-Alder reaction.arrow_forwardIf a molecule contains an aromatic ring, such as a benzene ring, attached to a non-aromatic ring, how does that affect the overall aromaticity of the molecule?arrow_forward
- Draw out the orbital structure and indicate if aromatic, antiaromatic, or non-aromatic furan thiophenearrow_forward2- Apply the polygon-and-circle method to the cyclopentadienyl cation and explain whether it would be aromatic or not. Cyclopentadienyl cationarrow_forwardProve the aromaticity of the following molecules by discussing | d)arrow_forward
- Explain how to construct the molecular orbitals of a conjugated cyclic system similar tobenzene and cyclobutadiene. Use the polygon rule to draw the energy diagram, and fillin the electrons to show whether a given compound or ion is aromatic or antiaromatic.arrow_forward2. State the two main experiments that were used to establish the extra stability of the benzene molecule. 3. What are the factors that confer Aromaticity to an organic molecule? 4. i. State the effects of substituents on a benzene derivative towards further aromatic substitution.arrow_forwardwhy is cyclopentadiene more acidic than cycloheptatriene?arrow_forward
- 3) In the mid-1930s, the German theoretical chemist Erich Hückel developed a rule that dealt with the aromaticity of various compounds, which became known as the Hückel Rule. Which (parts) of the compounds listed below are aromatic? Justify your answer based on Hückel's rule. You can treat the rings separately or together as you wish.arrow_forwardUse the inscribed polygon method to show the pattern of molecularorbitals in cyclooctatetraene. Classify the dianion of cyclooctatetraene as aromatic, antiaromatic, ornot aromatic, and explain why this is so.arrow_forwardExplain why the Diels Alder reaction would have synthetic significance in the production of biologically active compounds.arrow_forward
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