Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 15.SE, Problem 53AP
Consider the
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a. Consider the structure drawn below. Assuming the structure is planar, would you predict this compound to be aromatic, anti-aromatic, or nonaromatic? (Note: each nitrogen has a lone pair and, as drawn, each gallium has 6 valence electrons.) b. Explain your answer for part a: Which rules of aromaticity does the compound obey or disobey?
Why isn't this compound aromatic? Doesn't it fit the 4n+2 rule where there is 6 pi electrons? Or is it not planar, which is why it is not aromatic?
Is the following compound aromatic or not? Choose the correct answer (with motive ) from the options given
Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Give IUPAC names for the following compounds:Ch. 15.1 - Prob. 3PCh. 15.2 - Pyridine is a flat, hexagonal molecule with bond...Ch. 15.3 - Prob. 5PCh. 15.4 - Draw the five resonance structures of the...Ch. 15.4 - Prob. 7PCh. 15.4 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Prob. 10P
Ch. 15.6 - Prob. 11PCh. 15.6 - How many electrons does each of the four nitrogen...Ch. 15.SE - Give IUPAC names for the following substances (red...Ch. 15.SE - All-cis cyclodecapentaene is a stable molecule...Ch. 15.SE - 1, 6-Methanonaphthalene has an interesting 1H NMR...Ch. 15.SE - Prob. 16VCCh. 15.SE - Azulene, an isomer of naphthalene, has a...Ch. 15.SE - Give IUPAC names for the following compounds:Ch. 15.SE - Draw structures corresponding to the following...Ch. 15.SE - Prob. 20APCh. 15.SE - Prob. 21APCh. 15.SE - Draw and name all possible aromatic compounds with...Ch. 15.SE - Propose structures for aromatic hydrocarbons that...Ch. 15.SE - Look at the three resonance structures of...Ch. 15.SE - Prob. 25APCh. 15.SE - Prob. 26APCh. 15.SE - Look at the five resonance structures for...Ch. 15.SE - Prob. 28APCh. 15.SE - 3-Chlorocyclopropene, on treatment with AgBF4,...Ch. 15.SE - Prob. 30APCh. 15.SE - Prob. 31APCh. 15.SE - Prob. 32APCh. 15.SE - Which would you expect to be most stable,...Ch. 15.SE - How might you convert 1, 3, 5, 7-cyclononatetraene...Ch. 15.SE - Calicene, like azulene (Problem 15-17), has an...Ch. 15.SE - Pentalene is a most elusive molecule that has been...Ch. 15.SE - Prob. 37APCh. 15.SE - Prob. 38APCh. 15.SE - Compound A, C8H10, yields three substitution...Ch. 15.SE - Prob. 40APCh. 15.SE - Propose structures for compounds that fit the...Ch. 15.SE - Prob. 42APCh. 15.SE - Prob. 43APCh. 15.SE - N-Phenylsydnone, so-named because it was first...Ch. 15.SE - Prob. 45APCh. 15.SE - Prob. 46APCh. 15.SE - Prob. 47APCh. 15.SE - Propose a structure for a molecule C14H12 that has...Ch. 15.SE - The proton NMR spectrum for a compound with...Ch. 15.SE - The proton NMR spectrum of a compound with formula...Ch. 15.SE - Aromatic substitution reactions occur by addition...Ch. 15.SE - Prob. 52APCh. 15.SE - Consider the aromatic anions below and their...Ch. 15.SE - After the reaction below, the chemical shift of Ha...Ch. 15.SE - Prob. 55APCh. 15.SE - Azo dyes are the major source of artificial color...
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- Which of the molecules and ions given in Problem 21.15 are aromatic according to the Hckel criteria? Which, if planar, would be antiaromatic? 21.15 State the number of 2p orbital electrons in each molecule or ion.arrow_forwardThe unusual molecule below is aromatic and somewhat stable in spite of the positive charge on oxygen. Draw all possible resonance structures to show how the electrons can move about the ring in an uninterrupted circuit.arrow_forwardWhich of the following are consistent with the requirements for aromaticity?I. A system with delocalized p electrons in a ring.II. 4n p electrons in the ring.III. All the ring atoms must be carbons.IV. (4n + 2) p electrons in the ring. Give the answer why.arrow_forward
- How many additional resonance forms can be drawn for phenanthrene shown below?arrow_forwardDraw just the bonding p-MO’s for the cycloheptatrienyl cation. Draw the energy diagram to show the relative energies of all the MO’s, and show which orbitals the electrons would occupy in the ground state. Predict whether this ion is aromatic, antiaromatic, or nonaromatic.arrow_forwardPropose the electronic mechanism for the reaction, use curved arrows to show the flow of the electrons ir each step with the respective formal charges.arrow_forward
- Which of these images are not aromatic?arrow_forwardAside from the multiple ring systems shown in the table, search for 1 multiple ring aromatic compound and list down its properties, sources, and uses or applications.arrow_forward3) 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_forward
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