Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 15, Problem 15.48AP
Interpretation Introduction
Interpretation:
The explanation as to why the given compound is not aromatic is to be stated.
Concept introduction:
According to
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Of the following compounds,
+
are aromatic.
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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?
If 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?
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42APCh. 15 - Prob. 15.43APCh. 15 - Prob. 15.44APCh. 15 - Prob. 15.45APCh. 15 - Prob. 15.46APCh. 15 - Prob. 15.47APCh. 15 - Prob. 15.48APCh. 15 - Prob. 15.49APCh. 15 - Prob. 15.50APCh. 15 - Prob. 15.51APCh. 15 - Prob. 15.52APCh. 15 - Prob. 15.53APCh. 15 - Prob. 15.54APCh. 15 - Prob. 15.55APCh. 15 - Prob. 15.56APCh. 15 - Prob. 15.57APCh. 15 - Prob. 15.58APCh. 15 - Prob. 15.59APCh. 15 - Prob. 15.60APCh. 15 - Prob. 15.61APCh. 15 - Prob. 15.62APCh. 15 - Prob. 15.63APCh. 15 - Prob. 15.64APCh. 15 - Prob. 15.65APCh. 15 - Prob. 15.66APCh. 15 - Prob. 15.67APCh. 15 - Prob. 15.68APCh. 15 - Prob. 15.69APCh. 15 - Prob. 15.70APCh. 15 - Prob. 15.71APCh. 15 - Prob. 15.72APCh. 15 - Prob. 15.73APCh. 15 - Prob. 15.74APCh. 15 - Prob. 15.75APCh. 15 - Prob. 15.76APCh. 15 - Prob. 15.77APCh. 15 - Prob. 15.78APCh. 15 - Prob. 15.79APCh. 15 - Prob. 15.80APCh. 15 - Prob. 15.81APCh. 15 - Prob. 15.82APCh. 15 - Prob. 15.83APCh. 15 - Prob. 15.84APCh. 15 - Prob. 15.85APCh. 15 - Prob. 15.86AP
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- Heteroaromatic Structures Aromatic compounds which contain non-carbon atoms (e.g., O, N, S) as part of the cyclic conjugated a system are called heteroaromatics. the ring OR a lone pair in a p-orbital. Only one p The heteroatom can be a part of the conjugation as either part of a r bond orbital from the atom can align to contribute to the aromaticity. For example, let's look at furan (shown to the right). How many lone pairs are on the oxygen in this structure? O 3 lone pairs O 1 lone pair O 2 lone pairs O O lone pairs How many electrons are in the r bonds? O 0 electrons O 4 electrons O 2 electrons O 1 electron O 5 electrons O 3 electrons O 6 electrons To determine, the total number of x electrons to use for the Huckel calculation, you need to determine how many of the non-bonding electrons on the oxygen are aligned with the x bonds. Is the red orbital on oxygen aligned with r bonds? O yes O no Is the blue orbital on oxygen aligned with x bonds? O no O yes What is the total number of…arrow_forwardState which of the following compounds is/are aromatic and non-aromatic? Classify the compounds based on Hückel's Rule by providing their n values. II II IVarrow_forwardIs the following molecule/compound aromatic or not aromatic? Choose the correct answer (and motive) from options provided ( ZI O It has 10 T aelectrons, therefore aromatic It has 6 m electrons and satisfy Hückel's rule, therefore aromatic O is not aromatic because it has 10 m electrons and does not satisfy Huckel's rule for aromatic compounds O It has 8 mr electrons, and therefore aromaticarrow_forward
- 2. The molecular structure of perylene (see below) contains 20 m-electrons, which is not a Hückel number. Nonetheless, this compound is aromatic. Explain. 88 perylenearrow_forwardCyclopropenones are described as having aromatic character. How would you account for this, given that the ring contains three π-electrons?arrow_forwardThe compound MON-0585 is a non-toxic, biodegradable larvicide that is highly selective against mosquito larvae. Synthesize MON-0585 using either benzene or phenol as a source of the aromatic rings.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. IMAGE IV: colchicine: a highly poisonous alkaloid, obtained from autumn turmeric and used to treat gout.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.image iv: colchicine: a highly poisonous alkaloid,obtained from autumn turmeric and used to treat gout.arrow_forwardOne of the four criteria of aromaticity by Hückel is planarity of the rings containing 4n+2 electrons. Based on the Hückel rules, can a compound be aromatic but not planar? Please explain your answer.arrow_forward
- Cyclopropenones are described as having aromatic character. How would you account for this, given that the ring contains three ℼ-electronarrow_forwardSome of the following compounds show aromatic properties, and others do not. Predict which ones are likely to be aromatic, and explain why they are aromatic or not.arrow_forwardAromatic heterocyclic chemistry: State whether the following drugs are aromatic heterocycles and if they follow the 4 aromaticity rules (unsaturation, (4n + 2)pi electrons, cyclic and flat/planar), NAME ANY HETEROCYCLES. Draw the structure of the core of any aromatic heterocycles in the drug. Riociguat, Imatinib, Clopidogrel, Glatiramer acetate, Axitinibarrow_forward
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