ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Question
Chapter 15, Problem 48P
Interpretation Introduction
(a)
Interpretation: The
Concept introduction: The inscribed polygon method is helpful to predict whether a compound involves completely filled bonding
Interpretation Introduction
(b)
Interpretation: The arrangement of electrons in the
Concept introduction: The inscribed polygon method is helpful to predict whether a compound involves completely filled bonding
Interpretation Introduction
(c)
Interpretation: The number of
Concept introduction: The inscribed polygon method is helpful to predict whether a compound involves completely filled bonding
Interpretation Introduction
(d)
Interpretation: The arrangement of
Concept introduction: The inscribed polygon method is helpful to predict whether a compound involves completely filled bonding
Interpretation Introduction
(e)
Interpretation: The classification of dianion as aromatic, nonaromatic, or antiaromatic is to be stated and its being so is to be explained.
Concept introduction: The inscribed polygon method is helpful to predict whether a compound involves completely filled bonding
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59. Bond Strength
I. Cyclobutane
II. Cyclopentane
60. Optical Rotation
I. 70% R, 30% S
11.30% R, 70% S
61. Which of the following is/ are alternant aromatic compounds?
A. benzene
B. naphthalene
C. anthracene
D. all of the given choices
62. Which of the following is/ are not aromatic?
A. Cyclobutadiene
B. Cyclopentadiene
C. Cyclohexadiene
D. All of the given choices
63. The following can exhibit tautomerism EXCEPT:
A. benzaldehyde
B. ethanal
C. Cyclohexane carbaldehyde
D. Cyclohexanone
64. Which of the following substituents exhibits both - inductive effect and -
Resonance effect when attached to the benzene ring?
A. -OH B. -CI D. -NO2 D.-CH3
65. Alkyl groups if attached to halogen (example: tert-butyl bromide) would
exhibit
A. negative inductive effect
B. positive inductive effect
C. negative resonance effect
D. positive resonance effect.
9
Following the instructions for drawing the energy levels of the molecular orbitals for the compounds shown in Figure 8.17, draw the energy levels of the molecular orbitals for the cycloheptatrienyl cation, the cycloheptatrienyl anion, and the cyclopropenyl cation. For each compound, show the distribution of the p electrons. Which of the compounds are aromatic?
1.Discuss how aromaticity is affected in large ring compounds.
2. Discuss the aromaticity of heterocyclic compounds.
3. Discuss the aromaticity of polynuclear hydrocarbons
Chapter 15 Solutions
ORGANIC CHEMISTRY
Ch. 15.2 - Prob. 1PCh. 15.2 - Problem 17.2 What orbitals are used to form the...Ch. 15.3 - Prob. 4PCh. 15.3 - Problem-17.5 What is the structure of propofol,...Ch. 15.6 - Prob. 7PCh. 15.8 - Prob. 8PCh. 15.8 - Prob. 11PCh. 15.8 - Prob. 12PCh. 15.8 - Problem 17.16 Rank the following compounds in...Ch. 15.8 - Problem 17.17 Draw the seven resonance structures...
Ch. 15 - 17.23 Name each compound and state how many lines...Ch. 15 - Prob. 21PCh. 15 - Prob. 22PCh. 15 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 15 - 17.28 Draw a structure corresponding to each...Ch. 15 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - 17.38
How many electrons does C contain?
How...Ch. 15 - Prob. 36PCh. 15 - 17.40 Explain the observed rate of reactivity of...Ch. 15 - 17.41 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 39PCh. 15 - 17.43 Draw additional resonance structures for...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 17.46 Which compound in each pair is the stronger...Ch. 15 - 17.47 Treatment of indene with forms its...Ch. 15 - Prob. 45PCh. 15 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 15 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 15 - Prob. 48PCh. 15 - Prob. 49PCh. 15 - 17.53 How many signals does each compound...Ch. 15 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 15 - 17.55 Propose a structure consistent with each...Ch. 15 - 17.56 Propose a structure consistent with each...Ch. 15 - 17.57 Thymol (molecular formula ) is the major...Ch. 15 - 17.58 You have a sample of a compound of molecular...Ch. 15 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 15 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 15 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 15 - 17.62 Answer the following questions about...Ch. 15 - 17.63 Stanozolol is an anabolic steroid that...Ch. 15 - Prob. 61P
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- question 6. Which of the following is anti-aromatic?arrow_forwardINSTRUCTIONS: Choose the letter of the BEST answer for each item. 1. How many lone pairs are involved in sustaining the conjugation of pyridine? A. One B. Two C. Three D. Four 2. Benzopyrene, naphthalene and pyrene are members of these group of aromatic compounds: A. Benzenoid aromatic compounds B. Non-benzenoid aromatic compounds C. Heterocyclic aromatic compounds D. Heteronuclear compounds 3. What type of aromatic compound is pyridine? A. Heterocyclic aromatic compound B. Benzenoid aromatic compound C. Non-benzenoid aromatic compound D. Homonuclear cyclic compound 4. What property of aromatic rings prevent the involvement of the conjugated structure to addition reactions? A. Radical stabilization B. Resonance stability C. Inductive effect D. Aromatic effect 5. Which electrophilic aromatic substitution reaction is described when aniline is transformed into para-aminotolouene? A. Nitration B. Friedel Crafts alkylation C. Oxidation D. Halogenation 6. What type of relationship does…arrow_forward2. Which structure is NOT aromatic? a d. H3C :Br: DOarrow_forward
- 41. Draw the structure of a hydrocarbon that has six carbon atoms and a. three vinylic hydrogens and two allylic hydrogens. b. three vinylic hydrogens and one allylic hydrogen. c. three vinylic hydrogens and no allylic hydrogens.arrow_forwardHow many moles of Bra are required to completely halogenate the alkene?A. One moleB. Two molesC. Three molesD. Four moles What is the expected arrangement of the bromine atoms relative to each other amongthe carbon involved in pi bonding?A. anti-conformationB. syn-conformationC. trans-configurationD. cis-configuration What happens to bromine when it is adjacent to an alkene during a chemical reaction?A. Bromine becomes stable. (? kasi before brown siya/acidic tas naging colorless? Jk ewan)B. Bromine becomes polarized.C. Bromine becomes hybridized.D. Bromine becomes acidic. The relative arrangement of bromine atoms in the product is primarily due to:A. ElectronegativityB. RepulsionC. Hydrogen bondingD. Atomic weightWhat is your observation after the reaction?A. A yellow flame is produced.B. Bromine water decolorizes.C. The alkene becomes denser.D. A brown precipitate forms.arrow_forward1. Piperonal is a natural product found in various plants, such as dill and black pepper. Answer the questions below about piperonal. H. A E piperonal A. What is the hybridization of this carbon? B. How many H's does this carbon have? C. What is this functional group called? D. What is the molecular geometry of this carbon? E. What is the hybridization of this carbon? F. What is the strongest intermolecular interaction piperonal can participate in? G. How many degrees of unsaturation does piperonal have? H. How many 'H NMR signals would piperonal have? I. How many 13C NMR signals would piperonal have?arrow_forward
- A 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_forwardDetermine if the following compounds are aromatic, non-aromatic, or anti-aromatic. Show a structure that helps to support your classification. This structure should not just redraw the compound; show lone pairs, resonance, and/or contributing π bonds as part of your explanation.arrow_forwardWhich of the following is not a Huckel's criterion for aromaticity to. a.the molecule must have 4n pi electrons b. no alternative is correct c. the molecule must be fully conjugated d. the molecule must be flat and. e.the molecule must be cyclicarrow_forward
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