Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 17, Problem 17.52P
Interpretation Introduction
Interpretation: The pattern of molecular orbitals in cyclonona-
Concept introduction: The inscribed polygon method is helpful to predict whether a compound involves completely filled bonding
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Use the inscribed polygon method to show the pattern of molecular orbitals in cyclonona-1,3,5,7-tetraene, and use it to label its cation, radical, and anion as aromatic, antiaromatic, or not aromatic.
3. Use the inscribed polygon method to show the pattern of molecular orbitals of the following
cyclononatetraenyl cation and anion. Explain their aromaticity.
cyclononatetraenyl
cation
cyclononatetraenyl
anion
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…
Chapter 17 Solutions
Organic Chemistry-Package(Custom)
Ch. 17 - Prob. 17.1PCh. 17 - What orbitals are used to form the bonds indicated...Ch. 17 - Give the IUPAC name for each compound.Ch. 17 - Prob. 17.4PCh. 17 - Problem-17.5 What is the structure of propofol,...Ch. 17 - Problem 17.6 What is the structure of a compound...Ch. 17 - How many 13C NMR signals does each compound...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Problem 17.14 Januvia, the trade name for...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - Prob. 17.27PCh. 17 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 17 - 17.28 Draw a structure corresponding to each...Ch. 17 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - Prob. 17.33PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.35PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 17 - 17.38
How many electrons does C contain?
How...Ch. 17 - Prob. 17.39PCh. 17 - 17.40 Explain the observed rate of reactivity of...Ch. 17 - 17.41 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 17.42PCh. 17 - 17.43 Draw additional resonance structures for...Ch. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - 17.46 Which compound in each pair is the stronger...Ch. 17 - 17.47 Treatment of indene with forms its...Ch. 17 - Prob. 17.48PCh. 17 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 17 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - 17.53 How many signals does each compound...Ch. 17 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 17 - 17.55 Propose a structure consistent with each...Ch. 17 - 17.56 Propose a structure consistent with each...Ch. 17 - 17.57 Thymol (molecular formula ) is the major...Ch. 17 - 17.58 You have a sample of a compound of molecular...Ch. 17 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 17 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 17 - 17.62 Answer the following questions about...Ch. 17 - 17.63 Stanozolol is an anabolic steroid that...Ch. 17 - Prob. 17.63PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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- 3) Outline an acceptable step by step mechanism for the Nucleophilic aromatic substitution of ortho-fluoronitrobenzene with methylamine. Do not forget to include the formal charges of all non-hydrogen atoms that do not have a neutral charge.arrow_forwardA benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.arrow_forwardDo not handwriting solution.arrow_forward
- Fill the blank space. Compounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and ---------. The correct name (or abbreviation) of an example compound containing a phenol group with antioxidant properties is: ---------.arrow_forwardSubstituents on an aromatic ring can have several effects on electrophilic aromatic substitution reactions. Substituents can activate or deactivate the ring to substitution, donate or withdraw electrons inductively, donate or withdraw electrons through resonance, and direct substitution either to the ortho/para or to the meta positions. From the lists of substituents, select the substituents that correspond to each indicated property. The substituents are written as –XY, where X is the atom directly bound to the aromatic ring. These substituents activate the ring These substituents withdraw electrons towards substitution. through resonance. -CN -COOH -CH, O -OCH, -NO, O -NH, -NHCOCH, -CN Incorrect These substituents give ortho/para-directed substitution. -F -CH,arrow_forwardCompounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and The correct name (or abbreviation) of an example compound (discussed in the lecture videos) containing a phenol group with antioxidant properties is:arrow_forward
- What type of substituent effect do you expect a -CC12-CC12-CC13 (perchloropropyl) group to have upon aromatic electrophilic substitution reactions? Resonance electron donor; activating substituent; ortho/para director Inductive electron donating; activating substituent; ortho/para director Resonance electron withdrawing; deactivating substituent; ortho/para director Inductive electron withdrawing; deactivating substituent; meta directorarrow_forward5) Draw resonance structures for both carbanion and carbocation showing aromaticity and anti- aromaticity, respectively. This practice gives a proof for the cyclic delocalization. AROMATIC (10 e) ANTI-AROMATIC (8 e) allowing benzene analogs and other aromatic compounds.arrow_forwardConsider the structure of the cyclopentadienyl anion. cyclopentadienyl anion Complete the Frost circle (i.e., use the inscribed polygon method) for the anion. Classify the aromaticity of the compound. Aromatic Nonaromatic Antiaromatic Energy Answer Bank 1 1.arrow_forward
- Rank the following groups in order of their ability to activate an aromatic compound to electrophilic aromatic substitution.arrow_forward11:38 1. Is the following compound aromatic or not? Motivate your answer by using Huckel's rule." 2. Show a reaction scheme with all the reactants and reagents of the nitration reaction of bromobenzene and show the major products(s), with valid reasons motivate why the positioning of the two constituents' favour ortho, para and/or meta positioning Add a caption... > Status (Custom) +arrow_forwardThe heterocyclopentadienes listed contain more than one heteroatom. For each molecule, identify the orbitals occupied by each lone pair and determine whether the molecule is aromatic. For the sulfur and oxygen, two sets of lone pairs will each be in a different orbital, so place 2 orbitals in the box. N. 4 pyrazole Aromatic or not? P isoxazole pyrazole imidazole thiazole H imidazole Answer Bank non-aromatic aromatic Which heterocycles are more basic than pyrrole? sp² thiazole :0: isoxazolearrow_forward
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