Organic Chemistry, Books a la Carte Edition (8th Edition)
Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 8.13, Problem 35P

a)

Interpretation Introduction

Interpretation:

  • The rate determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product.  The reactions that produce the kinetic product as the major product are said to be kinetically controlled.  The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product.  The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled.  The thermodynamic product predominates when the reaction is reversible.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3carbocation > 2 carbocation > 1 carbocation > methyl cation > vinyl cation

b)

Interpretation Introduction

Interpretation:

  • The product determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product.  The reactions that produce the kinetic product as the major product are said to be kinetically controlled.  The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product.  The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled.  The thermodynamic product predominates when the reaction is reversible.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3carbocation > 2 carbocation > 1 carbocation > methyl cation > vinyl cation

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1. Alkene Addition Reaction Mechanisms: Draw the product for the addition reactions below in the boxes. Then, draw the FULL electron-pushing mechanism for the reactions, including all intermediates (with formal charges and lone pairs of electrons) and all electron pushing arrows. For each step, label the electrophile and nucleophile and name what type of elementary step it is. a. Addition of H-Br to an alkene: of b. Addition of H₂O using an acid catalyst: H-CI: H-Ö-SO₂H (cat.) H₂O
a.What carbon radical is formed by homolysis of the C–Ha bond in propylbenzene? Draw all reasonable resonance structures for this radical. b.What carbon radical is formed by homolysis of the C–Hb bond in propylbenzene? Draw all reasonable resonance structures for this radical. c. The bond dissociation energy of one of the C–H bonds is considerably less than the bond dissociation energy of the other. Which C–H bond is weaker? Offer an explanation.
When HBr adds to a conjugated diene, what is the product-determining step?

Chapter 8 Solutions

Organic Chemistry, Books a la Carte Edition (8th Edition)

Ch. 8.7 - Prob. 12PCh. 8.7 - Prob. 13PCh. 8.8 - Prob. 14PCh. 8.8 - Prob. 15PCh. 8.8 - Prob. 16PCh. 8.9 - Which member of each pair is the stronger acid?Ch. 8.9 - Which member of each pair is the stronger base? a....Ch. 8.9 - Rank the following compounds from strongest acid...Ch. 8.10 - Prob. 20PCh. 8.10 - Which acid in each of the following pairs is...Ch. 8.10 - Prob. 23PCh. 8.11 - Prob. 24PCh. 8.11 - Prob. 26PCh. 8.12 - Prob. 27PCh. 8.12 - Prob. 28PCh. 8.12 - Prob. 29PCh. 8.12 - Prob. 30PCh. 8.12 - Prob. 31PCh. 8.12 - Prob. 32PCh. 8.13 - Prob. 33PCh. 8.13 - Prob. 34PCh. 8.13 - Prob. 35PCh. 8.13 - What are the major 1,2- and 1,4-addition products...Ch. 8.13 - Prob. 38PCh. 8.14 - Prob. 39PCh. 8.14 - Prob. 40PCh. 8.14 - Prob. 41PCh. 8.14 - Prob. 42PCh. 8.14 - Prob. 43PCh. 8.14 - Prob. 44PCh. 8.14 - Prob. 46PCh. 8.15 - Prob. 47PCh. 8.17 - Prob. 48PCh. 8.17 - Prob. 49PCh. 8.18 - Prob. 50PCh. 8.18 - Prob. 52PCh. 8.18 - Prob. 53PCh. 8.18 - Prob. 54PCh. 8.19 - Prob. 55PCh. 8.20 - Prob. 56PCh. 8.20 - What orbitals contain the electrons represented as...Ch. 8.20 - Prob. 59PCh. 8.20 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - Prob. 65PCh. 8 - Prob. 66PCh. 8 - Prob. 67PCh. 8 - Prob. 68PCh. 8 - Prob. 69PCh. 8 - Prob. 70PCh. 8 - Prob. 71PCh. 8 - Prob. 72PCh. 8 - Prob. 73PCh. 8 - Which compound is the strongest base?Ch. 8 - Prob. 75PCh. 8 - Prob. 76PCh. 8 - a. The A ring (Section 3.16) of cortisone (a...Ch. 8 - Prob. 78PCh. 8 - Prob. 79PCh. 8 - Prob. 80PCh. 8 - Prob. 81PCh. 8 - Purine is a heterocyclic compound with four...Ch. 8 - Prob. 83PCh. 8 - Why is the delocalization energy of pyrrole (21...Ch. 8 - Prob. 85PCh. 8 - Prob. 86PCh. 8 - Prob. 87PCh. 8 - A student obtained two products from the reaction...Ch. 8 - Prob. 89PCh. 8 - a. How could each of the following compounds be...Ch. 8 - Draw the products obtained from the reaction of...Ch. 8 - How would the following substituents affect the...Ch. 8 - Prob. 93PCh. 8 - The acid dissociation constant (Ka) for loss of a...Ch. 8 - Protonated cyclohexylamine has a Ka = 1 1011...Ch. 8 - Draw the product or products that would be...Ch. 8 - Prob. 97PCh. 8 - Prob. 98PCh. 8 - Prob. 99PCh. 8 - Prob. 100PCh. 8 - Prob. 101PCh. 8 - a. Propose n mechanism for the following reaction:...Ch. 8 - Prob. 103PCh. 8 - As many as 18 different Diels-Alder products can...Ch. 8 - Prob. 105PCh. 8 - Prob. 106PCh. 8 - Prob. 107PCh. 8 - Prob. 108PCh. 8 - The experiment shown next and discussed in Section...Ch. 8 - Prob. 110PCh. 8 - Prob. 111PCh. 8 - Prob. 112PCh. 8 - Prob. 1PCh. 8 - Prob. 2PCh. 8 - Prob. 3PCh. 8 - Prob. 4PCh. 8 - Prob. 5PCh. 8 - Prob. 6PCh. 8 - Prob. 7PCh. 8 - Prob. 8PCh. 8 - Prob. 9PCh. 8 - Prob. 10PCh. 8 - Prob. 11PCh. 8 - Prob. 12P
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