- 8.71P: ?Which can lose a proton more readily, a methyl group bonded to cyc...
- 8.72P: The triphenylmethyl cation is so stable that a salt such as triphen...
- 8.73P: ?1. The B ring ( Section \(3.15\) ) of cortisone, a steroid, is for...
- 8.74P: ?Answer the following questions and explain the reason for each ans...
- 8.75P: ?Draw the resonance contributors for the following anion and rank t...
- 8.76P: ?Rank the following compounds in order from most stable to least st...
- 8.77P: ?Which species in each pair is more stable?
- 8.78P: ?Which species in each of the pairs in \(\text{Problem} \ 77\) is t...
- 8.79P: ?Purine is a heterocyclic compound with four nitrogen atoms.a. Whic...
- 8.80P: ?Which of the following compounds is the strongest acid?
- 8.81P: ?Why is the delocalization energy of pyrrole \((21 \ \mathrm{kcal} ...
- 8.9P: a. What is the value of n in Hückel’s rule when a compound has nine...
- 8.82P: ?Rank the indicated hydrogen in the following compounds in order fr...
- 8.21P: How many bonding, nonbonding, and antibonding ? molecular orbitals ...
- 8.22P: Can a radical be aromatic?
- 8.83P: Answer the following questions for the ? molecular orbitals (MOs) o...
- 8.84P: ?How could you synthesize the following compound from starting mate...
- 8.85P: A student obtained two products from the reaction of 1,3-cyclohexad...
- 8.86P: ?How could the following compounds be synthesized using a Diels–Ald...
- 8.87P: ?1. How could each of the following compounds be prepared from a hy...
- 8.88P: Draw the products obtained from the reaction of 1 equiv HBr with 1 ...
- 8.89P: How would the following substituents affect the rate of a Diels–Ald...
- 8.90P: Give the major products obtained from the reaction of one equivalen...
- 8.91P: ?The acid dissociation constant \((\mathrm{K}_\mathrm{a})\) for los...
- 8.92P: ?Protonated cyclohexylamine has a \(\mathrm{K}_\mathrm{a} = 1 \time...
- 8.93P: ?Draw the product or products that would be obtained from each of t...
- 8.94P: ?What two sets of a conjugated diene and a dienophile could be used...
- 8.95P: ?1. Which dienophile in each pair is more reactive in a Diels–Alder...
- 8.96P: Cyclopentadiene can react with itself in a Diels–Alder reaction. Dr...
- 8.97P: ?Which diene and which dienophile could be used to prepare each of ...
- 8.10P: ?Which compound in each set is aromatic? Explain your choice.
- 8.98P: ?1. Propose a mechanism for the following reaction: 2. What is the ...
- 8.11P: The pKa of cyclopentane is > 60, which is about what is expected fo...
- 8.100P: As many as 18 different Diels–Alder products can be obtained by hea...
- 8.99P: ?1. What are the products of the following reaction? 2. How many st...
- 8.23P: Following the instructions for drawing the ? molecular orbital ener...
- 8.101P: On a single graph, draw the reaction coordinate diagram for the add...
- 8.34P: ?A methoxy substituent attached to a benzene ring withdraws electro...
- 8.35P: ?What is the major product obtained from the addition of \(H B r\) ...
- 8.102P: ?While attempting to recrystallize maleic anhydride, a student diss...
- 8.36P: ?Predict the sites on each of the following compounds where protona...
- 8.103P: ?The following equilibrium is driven to the right if the reaction i...
- 8.104P: ?In \(1935\), J. Bredt, a German chemist, proposed that a bicycloal...
- 8.46P: ?What are the major \(1,2-\text { and } 1,4-\) addition products of...
- 8.105P: ?The experiment shown next and discussed in \(\text{Section} \ 8.18...
- 8.47P: ?Identify the kinetic and thermodynamic products of the following r...
- 8.106P: ?The product of the following reaction has a fused bicyclic ring. W...
- 8.107P: Draw the resonance contributors of the cyclooctatrienyl dianion.a. ...
- 8.48P: ?What are the products of the following reactions?
- 8.108P: ?Investigation has shown that cyclobutadiene is actually a rectangu...
- 8.1P: ?a. The following compounds have the same molecular formula as benz...
- 8.2P: ?Between \(1865\) and \(1890\), other possible structures were prop...
- 8.12P: ?Which of the following are aromatic?
- 8.13P: ?a. In what direction is the dipole moment in fulvene? Explain.b. I...
- 8.14P: ?What orbital do the lone-pair electrons occupy in each of the foll...
- 8.24P: The heat of hydrogenation of 2,3-pentadiene, a cumulated diene, is ...
- 8.25P: ?Name the following dienes and rank them in order from most stable ...
- 8.26P: ?Which carbocation in each pair is more stable? b. \(\mathrm{CH}_{3...
- 8.37P: ?What is the major product of each of the following reactions, assu...
- 8.38P: ?Which of the double bonds in zingiberene, the compound responsible...
- 8.39P: ?What are the products of the following reactions, assuming that on...
- 8.49P: ?What would be the major product if the methoxy substituent in the ...
- 8.50P: Write a general rule that can be used to predict the major product ...
- 8.51P: ?What two products are formed from each of the following reactions?
- 8.3P: ?a. Which of the following compounds have delocalized electrons?1. ...
- 8.4P: ?Draw resonance contributors for each of the following species and ...
- 8.5P: ?Draw the resonance hybrid for each of the species in \(4\) Equatio...
- 8.15P: What orbitals contain the electrons represented as lone pairs in th...
- 8.16P: ?Which of the following compounds could be protonated without destr...
- 8.17P: Refer to the electrostatic potential maps on page 347 to answer the...
- 8.27P: ?What is the total number of nodes in the \(\psi_{3} \text { and } ...
- 8.28P: Answer the following questions for the ? MOs of 1,3-butadiene:a. Wh...
- 8.29P: ?The most stable \(M O\) of \(1,3,5\)-hexatriene and the most stabl...
- 8.40P: ?What stereoisomers are obtained from the two reactions shown on th...
- 8.41P: What products would be obtained from the reaction of 1,3,5-hexatrie...
- 8.42P: ?What are the products of the following reactions, assuming that on...
- 8.52P: ?Which of the following conjugated dienes would not react with a di...
- 8.53P: ?What are the products of the following reactions?
- 8.55P: Explain why the following compounds are not optically active:a. the...
- 8.6P: a. Predict the relative bond lengths of the three carbon-oxygen bon...
- 8.7P: ?Which species in each pair is more stable?
- 8.8P: ?Which of the following species has the greatest delocalization ene...
- 8.18P: a. Predict the relative pKa values of cyclopentadiene and cyclohept...
- 8.19E: Which is more soluble in water, 3-bromocyclopropene or bromocyclopr...
- 8.20P: ?Which of the compounds in \(12\) are antiaromatic? Equation Transc...
- 8.30P: ?Which member of each pair is the stronger acid?
- 8.31P: Which is a stronger base?a. ethylamine or anilineb. ethylamine or e...
- 8.32P: ?Rank the following compounds in order from strongest acid to weake...
- 8.56P: ?What diene and what dienophile should be used to synthesize the fo...
- 8.57P: Which of the following have delocalized electrons?
- 8.43P: ?a. Why does deuterium add to \(C-1\) rather than to \(C-4\) in the...
- 8.44P: A student wanted to know whether the greater proximity of the nucle...
- 8.58P: a. Draw resonance contributors for the following species, showing a...
- 8.45P: a. When HBr adds to a conjugated diene, what is the rate-determinin...
- 8.59P: ?What is the major product of each of the following reactions? Assu...
- 8.60P: ?Draw resonance contributors for the following ions:
- 8.61P: ?Draw all the products of the following reaction:
- 8.62P: ?Are the following pairs of structures resonance contributors or di...
- 8.63P: a. How many linear dienes have molecular formula C6H10? (Disregard ...
- 8.64P: ?a. Draw resonance contributors for the following species. Do not i...
- 8.65P: ?Which ion in each of the following pairs is more stable and why?
- 8.66P: Which compound would you expect to have the greater heat of hydroge...
- 8.67P: ?Which resonance contributor in each pair makes the greater contrib...
- 8.68P: ?Classify the following species as aromatic, nonaromatic, or antiar...
- 8.69P: ?a. Which oxygen atom has the greater electron density? b. Which co...
- 8.70P: ?Which compound is the strongest base?
- 8.57: Which of the following have delocalized electrons?
- 8.58: a. Draw resonance contributors for the following species, showing a...
- 8.59: What is the major product of each of the following reactions? Assum...
- 8.60: Draw resonance contributors for the following ions:
- 8.61: Draw all the products of the following reaction:
- 8.62: Are the following pairs of structures resonance contributors or dif...
- 8.63: a. How many linear dienes have molecular formula C 6 H 10 ? (Disreg...
- 8.64: a. Draw resonance contributors for the following species. Do not in...
- 8.65: Which ion in each of the following pairs is more stable and why?
- 8.66: Which compound would you expect to have the greater heat of hydroge...
- 8.67: Which resonance contributor in each pair makes the greater contribu...
- 8.68: Classify the following species as aromatic, nonaromatic, or antiaro...
- 8.69: a. Which oxygen atom has the greater electron density?
- 8.70: Which compound is the strongest base?
- 8.71: Which can lose a proton more readily, a methyl group bonded to cycl...
- 8.72: The triphenylmethyl cation is so stable that a salt such as triphen...
- 8.73: a. The B ring ( Section 3.15 ) of cortisone, a steroid, is formed b...
- 8.74: Answer the following questions and explain the reason for each answer:
- 8.75: Answer the following questions and explain the reason for each answer:
- 8.76: Rank the following compounds in order from most stable to least sta...
- 8.77: Which species in each pair is more stable?
- 8.78: Which species in each of the pairs in is the stronger base?
- 8.79: Purine is a heterocyclic compound with four nitrogen atoms. a. Whic...
- 8.80: Which of the following compounds is the strongest acid?
- 8.81: Why is the delocalization energy of pyrrole (21 kcal/mol) greater t...
- 8.82: Rank the indicated hydrogen in the following compounds in order fro...
- 8.83: Answer the following questions for the p molecular orbitals (MOs) o...
- 8.84: How could you synthesize the following compound from starting mater...
- 8.85: A student obtained two products from the reaction of 1,3-cyclohexad...
- 8.86: How could the following compounds be synthesized using a DielsAlder...
- 8.87: a. How could each of the following compounds be prepared from a hyd...
- 8.88: Draw the products obtained from the reaction of 1 equiv HBr with 1 ...
- 8.89: How would the following substituents affect the rate of a DielsAlde...
- 8.90: Draw the major products obtained from the reaction of one equivalen...
- 8.91: The acid dissociation constant ( Ka ) for loss of a proton from cyc...
- 8.92: Protonated cyclohexylamine has a Ka = 1 * 10-11 . Using the same se...
- 8.93: Draw the product or products that would be obtained from each of th...
- 8.94: What two sets of a conjugated diene and a dienophile could be used ...
- 8.95: a. Which dienophile in each pair is more reactive in a DielsAlder r...
- 8.96: Cyclopentadiene can react with itself in a DielsAlder reaction. Dra...
- 8.97: Which diene and which dienophile could be used to prepare each of t...
- 8.98: a. Propose a mechanism for the following reaction:
- 8.99: a. What are the products of the following reaction? Br + 2 b. How m...
- 8.100: As many as 18 different DielsAlder products can be obtained by heat...
- 8.101: As many as 18 different DielsAlder products can be obtained by heat...
- 8.102: While attempting to recrystallize maleic anhydride, a student disso...
- 8.103: The following equilibrium is driven to the right if the reaction is...
- 8.104: In 1935, J. Bredt, a German chemist, proposed that a bicycloalkene ...
- 8.105: The experiment shown next and discussed in Section 8.18 shows that ...
- 8.106: The product of the following reaction has a fused bicyclic ring. Wh...
- 8.107: Draw the resonance contributors of the cyclooctatrienyl dianion. a....
- 8.108: Investigation has shown that cyclobutadiene is actually a rectangul...
Solutions for Chapter 8: Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction
Full solutions for Organic Chemistry | 7th Edition
ISBN: 9781269406772
Solutions for Chapter 8: Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction
Get Full SolutionsSummary of Chapter 8: Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction
Delocalized electrons play such an important role in organic chemistry that they will be a part of all the remaining chapters in this book. This chapter will start by showing you how delocalized electrons are depicted. Then you will see how they affect things that are now familiar to you, such as pKa values, the stability of carbocations, and the products formed from electrophilic addition reactions.
Chapter 8: Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction includes 158 full step-by-step solutions. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 7. This expansive textbook survival guide covers the following chapters and their solutions. Organic Chemistry was written by and is associated to the ISBN: 9781269406772. Since 158 problems in chapter 8: Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction have been answered, more than 500055 students have viewed full step-by-step solutions from this chapter.
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acid
A substance that is able to donate a H+ ion (a proton) and, hence, increases the concentration of H+1aq2 when it dissolves in water. (Section 4.3)
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barometer
An instrument that measures atmospheric pressure. (5.2)
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biodegradable
Organic material that bacteria are able to oxidize. (Section 18.4)
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decarboxylation
A reaction involving loss of CO2, characteristic of compounds containing a carbonyl group that is beta to a COOH group.
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degree of substitution
For alkenes, a classification method that refers to the number of alkyl groups connected to the double bond.
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delocalized
A lone pair or charge that is participating in resonance.
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E (Section 5.2C)
From the German, entgegen, opposite. Specifi es that groups of higher priority on the carbons of a double bond are on opposite sides
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ester
An organic compound that has an OR group attached to a carbonyl; it is the product of a reaction between a carboxylic acid and an alcohol. (Section 24.4)
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exo
In Diels-Alder reactions that produce bicyclic structures, the positions that are anti to the larger bridge.
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Fatty acid
A long, unbranched-chain carboxylic acid, most commonly of 12 to 20 carbons, derived from the hydrolysis of animal fats, vegetable oils, or the phospholipids of biological membranes.
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Furanose
A fi ve-membered cyclic form of a monosaccharide.
-
Gabriel synthesis
A method forpreparing primary amines that avoids formation of secondary and tertiary amines.
-
line spectrum
A spectrum that contains radiation at only certain specific wavelengths. (Section 6.3)
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Monosaccharide
A carbohydrate that cannot be hydrolyzed to a simpler carbohydrate.
-
Nitrogen rule
A rule stating that the molecular ion of a compound with an odd number of nitrogen atoms has an odd m/z ratio; if zero or an even number of nitrogen atoms, the molecular ion has an even m/z ratio
-
percent yield
The ratio of the actual (experimental) yield of a product to its theoretical (calculated) yield, multiplied by 100. (Section 3.7)
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Radical
Any chemical species that contains one or more unpaired electrons.
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silicates
Compounds containing silicon and oxygen, structurally based on SiO4 tetrahedra. (Section 22.10)
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specific rotation
For a chiral compound that is subjected to plane-polarized light, the observed rotation when a standard concentration (1 g/mL) and a standard path length (1 dm) are used.
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Terpene
A compound whose carbon skeleton can be divided into two or more units identical with the carbon skeleton of isoprene