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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

7 Propose structures for aromatic compounds that have the following 1HNMR spectra:

(a) C8H9BrIR=820 cm-1

b) C9H12IR:750 cm-1

c) C11H16IR:820 cm-1

Azulene, a beautiful blue hydrocarbon, is an isomer of naphthalene. Is azulene aromatic? Draw a second resonance form of azulene in addition to that shown.

Propose structures for compounds that fit the following descriptions:

(a) C10H141HNMR: 7.18 δ(4 H, broad singlet);2.70 δ(4 H, quartet, J = 7 Hz); 1.20 δ(6 H, triplet, J =7 Hz) IR:745 cm-1.

(b)C10H141HNMR:7.0 δ(4 H, broad singlet);2.85  δ(1 H, septet, J = 8 Hz);2.28  δ(3 H, singlet);1.20  δ(6 H, doublet, J = 8 Hz) IR:825 cm-1.

Draw structures corresponding to the following names:

(a) 3-Methyl-1,2-benzenediamine

(b) 1,3,5-Benzenetriol

(c) 3-Methyl-2-phenylhexane

(d) o-Aminobenzoic acid

(e) m-Bromophenol

(f) 2,4,6-Trinitrophenol (picric acid)

Give IUPAC names for the following compounds

b)

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