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Chapter 15: Q15-53E (page 477)

Draw all of the resonance forms for each. What patterns emerge?

Short Answer

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Tropylium cation or cycloheptatrienyl cation is aromatic with six pi electrons and its molecular formula isC7H7+and its molar mass is 91.132 g/mol.

Step by step solution

01

Tropylium cation

Tropylium cation or cycloheptatrienyl cation is aromatic with six pi electrons and its molecular formula isC7H7+and its molar mass is 91.132 g/mol.

02

a) Resonating forms of tropylium cation

The resonating forms of the tropylium cation are shown as follows:

The resonating form of other analog is as shown:

The patterns show that alternating double bonds in an organic compound are delocalized to a considerable extent which makes their properties different from the isolated olefinic double bonds.

03

b) Resonating forms of pyrrole anion

The resonating form of pyrrole anion is as shown:

The resonating form of the liner analog is as follows:

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Most popular questions from this chapter

Azo dyes are the major source of artificial color in textiles and food. Part of the reason for their intense coloring is the conjugation from an electron-donating group through the diazo bridge (-N=N-)to an electron-withdrawing group on the other side. For the azo dyes below, draw a resonance form that shows how the electron-donating group is related to the electron-withdrawing group on the other side of the diazo bridge. Used curved arrows to show how the electrons are reorganized.

a.

Methyl orange

b.

C.I. Acid Red 74

What is the structure of a hydrocarbon that hasM+=120in its mass spectrum and has the following1HNMR spectrum? 7.25 d (5 H, broad singlet); 2.90 d (1 H, septet, J 5 7 Hz); 1.22 d (6 H, doublet, J 5 7 Hz).

Draw and name all possible aromatic compounds with the formula C8H9Br.

Compound A,C8H10, yields three substitution products,C8H9Br, on reaction withBr2. Propose two possible structures for A. The1HNMR spectrum of A shows a complex four-proton multiplet at 7.0 d and a six-proton singlet at 2.30 d. What is the structure of A?

How might you convert 1, 3, 5, 7-cyclononatetraene to an aromatic substance?
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