Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 15.SE, Problem 53AP
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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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- Of Hückel's original rules for aromaticity, one needed to be revised. Which one is it? The ring system must be planar. There must be (4n + 2) pi electrons. The molecule must be monocyclic. The pi electrons must be resonance delocalized over the entire ring. QUESTION 17arrow_forwardUsing the concept of aromaticity and resonance, determine which of the following compounds has the greatest dipole moment. Explain your selectionarrow_forwardThe structure of Vitamin C (ascorbic acid) is shown below. As the name indicates, the molecule is somewhat acidic. Actually, one of the hydrogens on the four OH groups is much more acidic than the other three ones. Which one is the acidic hydrogen? Hints: To find the answer, you will again have to draw some resonance structures of the product formed after loss of H+. Consider the product after the loss of H+ for each of the OH groups. Only two of the OH groups have resonance structures after deprotonation; one of these two groups has a much better resonance structure than the other one (again after deprotonation). Note that the oxygen atom that is part of the five-membered ring has nothing to do with the problem.arrow_forward
- Define the consequence of resonance stabilization ?arrow_forwardHow come the structure labeled as 1 has 8 pi electrons? If the double bond has 2 pi electrons, and you count the lone pairs, wouldn't it have 6 pi electrons? Why does the structure labeled as 2 has aromaticity? If the pi bond has 2 pi electrons and then you coun the lone pairs, wouldn't it only have 5 pi electrons?arrow_forwardIs this structure aromatic, antiaromatic, or nonaromatic? Provide its resonance structure as well.arrow_forward
- 4. One of the resonance structures of "tropylium ion" (C7H7*) is shown below. It is planar and aromatic with Hückel number of p-n electrons where n=1. Draw all the other contributing resonance structures. (There are more than two.) Based on the “average" of the contributing resonance structures, how close does the average ring carbon get to its "octeť" in tropylium ion?arrow_forwardAromatic compounds must have a p orbital on every atom in the ring. Define this ?arrow_forwardGive the name of this compound and write its major and minor resonance structures. Label and explain every step.arrow_forward
- Should the final resonance structure be included in the radical resonance? Or is the first and fifth structure the same?arrow_forwardexplain part A by first drawing all the resonance structures for the four compounds please. and then write the explanaiton. HANDDRAW it instead of using text. thanksarrow_forwardOther than having 4n+ 2 pi electrons, which condition(s) must be met for a molecule to be aromatic The molecule must be planar. The molecule must be conjugated. The molecule must be a ring. All of the above.arrow_forward
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