(a) Interpretation: Each of the following compounds exists as a fluxional molecule that is interconverted into one or more identical forms by the sigmatropic process indicated. One structure in each case that demonstrates the process involved is to be drawn. Each process is an allowed pericyclic reaction – the statement is to be verified. Concept introduction: When a molecule undergoes a dynamic molecular motion involving the interchange of two or more groups which are chemically and magnetically different, then the molecule is said to have fluxionality nature. In this case, the signals corresponding to interchanged two or more groups will be identical, if the rate of exchange of the groups occurs very quickly. The fluxionality in organic molecules can be easily followed by multinuclear NMR spectroscopy.

Question

(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?(c) Draw resonance forms to show the charge distribution on the pyrrole structure.

Answer 1

Question

Chapter 28, Problem 28.24P

Interpretation Introduction

(a)

Interpretation:

Each of the following compounds exists as a fluxional molecule that is interconverted into one or more identical forms by the sigmatropic process indicated. One structure in each case that demonstrates the process involved is to be drawn. Each process is an allowed pericyclic reaction – the statement is to be verified.

Concept introduction:

When a molecule undergoes a dynamic molecular motion involving the interchange of two or more groups which are chemically and magnetically different, then the molecule is said to have fluxionality nature. In this case, the signals corresponding to interchanged two or more groups will be identical, if the rate of exchange of the groups occurs very quickly. The fluxionality in organic molecules can be easily followed by multinuclear NMR spectroscopy.

Interpretation Introduction

(b)

Interpretation:

Each of the following compounds exists as a fluxional molecule that is interconverted into one or more identical forms by the sigmatropic process indicated. One structure in each case that demonstrates the process involved is to be drawn. Each process is an allowed pericyclic reaction – the statement is to be verified.

Concept introduction:

When a molecule undergoes a dynamic molecular motion involving the interchange of two or more groups which are chemically and magnetically different, then the molecule is said to have fluxionality nature. In this case, the signals corresponding to interchanged two or more groups will be identical, if the rate of exchange of the groups occurs very quickly. The fluxionality in organic molecules can be easily followed by multinuclear NMR spectroscopy.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?(c) Draw resonance forms to show the charge distribution on the pyrrole structure.

(a) What monobromo allylic substitution products would result from reaction of each of PRACTICE P the following compounds with NBS in the presence of peroxides and/or light? (b) In the case of isomeric products for any reaction, which would you predict to be the most stable based on the double bond in the product? (c) Draw the resonance hybrid(s) for the allylic radical that would be involved in each reaction. (i) (ii) V dil.... (iii) oily

Provide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)