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Chapter 15: Q15-53E (page 477)

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

Short Answer

Expert verified

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

Propose structures for aromatic hydrocarbons that meet the following descriptions:

(a) C9H12; gives only one C9H11Brproduct on substitution of hydrogen on the aromatic ring with bromine

(b)C10 H14; gives only one C10H13Clproduct on substitution of hydrogen on the aromatic ring with chlorine

(c) C8H10; gives three C8H9Brproducts on substitution of hydrogen on the aromatic ring with bromine

(d)C10 H14 ; gives two C10H13Clproducts on substitution of hydrogen on the aromatic ring with chlorine

Calicene, like azulene (Problem 15-17), has an unusually large dipole moment for a hydrocarbon. Explain, using resonance structures.

Calicene

The proton NMR spectrum of a compound with formula C6H5NCl2is shown. The normal carbon-13 and DEPT experimental results are tabulated. The infrared spectrum shows peaks at 3432 and 3313鈥�cm-1and a series of medium-sized peaks between 1618 and 1466鈥�cm-1. Draw the structure of this compound.

How many electrons does each of the four nitrogen atoms in purine contribute to the aromatic system?

The following molecular model is that of a carbocation. Draw two resonance structures for the carbocation, indicating the positions of the double bonds.
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