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Chapter 17: Q.17. (page 641)

Question: Draw the seven resonance structures for the tropyllium cation.

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01

Resonance

In certain molecules or ions, the bonding occurs by combining different contributing structures or resonance structures into a hybrid structure. Resonance has a particular value for delocalization.

02

Example for resonance

An example for resonance using benzene is shown below:

Resonance structures of benzene

Different resonance structures can be obtained by shifting the bonds and the charges within the structure. The resonance structure of tropyllium is shown below:

Resonance structure of tropyllium

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Most popular questions from this chapter

Question: Propose a structure consistent with each set of data.

a. Compound A:

Molecular formula: C8H10O

IR absorption at role="math" localid="1648804967273" 3150-2850cm-1

H1NMR data: 1.4 (triplet, 3 H), 3.95 (quartet, 2 H), and 6.8–7.3 (multiplet, 5 H) ppm

b. Compound B:

Molecular formula: C9H10O2

IR absorption at role="math" localid="1648805107903" 1669cm-1

H1NMR data: 2.5 (singlet, 3 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.9 (doublet, 2 H) ppm

Question: The carbon–carbon bond lengths in naphthalene are not equal. Use a resonance argument to explain why bond (a) is shorter than bond (b).

Question: Which heterocycles are aromatic?

a.

b.

c.

d.

Question: Which compound in each pair is the stronger acid?

Question: (a) How is each N atom in quinine, an effective antimalarial drug that reduces fever, hybridized? (b) In what type of orbital does the lone pair on each N reside?
See all solutions

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