EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
7th Edition
ISBN: 9780133556186
Author: Bruice
Publisher: VST
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Chapter 8, Problem 104P
Interpretation Introduction

Interpretation: In accordance with Bredt’s rule, it should be explained that why there cannot be a double bond at a bridgehead carbon atom.

Concept introduction:

  • Bredt’s rule: This rule states that a bridged bicyclic compound cannot have a double bond at the bridgehead position unless one of the rings contains at least 8 carbon atoms.

According to this rule stable and unstable molecule is mentioned below,

EBK ORGANIC CHEMISTRY, Chapter 8, Problem 104P , additional homework tip  1EBK ORGANIC CHEMISTRY, Chapter 8, Problem 104P , additional homework tip  2

The first compound is stable. Although double bond is at bridgehead, the system is not bridged

But the second compound is the good example to illustrate the violation of this rule. This compound is unstable because double bond is at bridgehead and ring contains only 6 carbons.

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Chapter 8 Solutions

EBK ORGANIC CHEMISTRY

Ch. 8.9 - Prob. 13PCh. 8.10 - Prob. 14PCh. 8.10 - What orbitals contain the electrons represented as...Ch. 8.10 - Prob. 16PCh. 8.10 - Prob. 17PCh. 8.11 - Prob. 18PCh. 8.11 - Prob. 19PCh. 8.11 - Prob. 20PCh. 8.12 - Prob. 21PCh. 8.12 - Prob. 22PCh. 8.12 - Prob. 23PCh. 8.13 - Prob. 24PCh. 8.13 - Prob. 25PCh. 8.13 - Prob. 26PCh. 8.14 - Prob. 27PCh. 8.14 - Prob. 28PCh. 8.14 - Prob. 29PCh. 8.15 - Which member of each pair is the stronger acid?Ch. 8.15 - Which member of each pair is the stronger base? a....Ch. 8.15 - Rank the following compounds from strongest acid...Ch. 8.15 - Prob. 34PCh. 8.16 - Prob. 35PCh. 8.17 - Prob. 37PCh. 8.17 - Prob. 38PCh. 8.17 - Prob. 39PCh. 8.17 - Prob. 40PCh. 8.17 - Prob. 41PCh. 8.17 - Prob. 42PCh. 8.18 - Prob. 43PCh. 8.18 - Prob. 44PCh. 8.18 - Prob. 45PCh. 8.18 - Prob. 47PCh. 8.19 - Prob. 48PCh. 8.19 - Prob. 49PCh. 8.19 - Prob. 50PCh. 8.19 - Prob. 51PCh. 8.19 - Prob. 52PCh. 8.19 - Prob. 53PCh. 8.19 - Prob. 55PCh. 8.20 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Prob. 58PCh. 8 - Prob. 59PCh. 8 - 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 - Which compound is the strongest base?Ch. 8 - Prob. 71PCh. 8 - Prob. 72PCh. 8 - Prob. 73PCh. 8 - Prob. 74PCh. 8 - Prob. 75PCh. 8 - Prob. 76PCh. 8 - Prob. 77PCh. 8 - Prob. 78PCh. 8 - Purine is a heterocyclic compound with four...Ch. 8 - Prob. 80PCh. 8 - Why is the delocalization energy of pyrrole (21...Ch. 8 - Prob. 82PCh. 8 - Prob. 83PCh. 8 - Prob. 84PCh. 8 - A student obtained two products from the reaction...Ch. 8 - Prob. 86PCh. 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. 90PCh. 8 - The acid dissociation constant (Ka) for loss of a...Ch. 8 - Protonated cyclohexylamine has a Ka = 1 1011...Ch. 8 - Prob. 93PCh. 8 - Prob. 94PCh. 8 - Prob. 95PCh. 8 - Prob. 96PCh. 8 - Prob. 97PCh. 8 - a. Propose n mechanism for the following reaction:...Ch. 8 - Prob. 99PCh. 8 - As many as 18 different Diels-Alder products can...Ch. 8 - Prob. 101PCh. 8 - Prob. 102PCh. 8 - Prob. 103PCh. 8 - Prob. 104PCh. 8 - The experiment shown next and discussed in Section...Ch. 8 - Prob. 106PCh. 8 - Prob. 107PCh. 8 - Prob. 108PCh. 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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