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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: Give the IUPAC name for each compound.

a.

b.

c.

d.

Question: Early structural studies on benzene had to explain the following experimental evidence. When benzene was treated with Br2(plus a Lewis acid), a single substitution product of molecular formula C6H5Brwas formed. When this product was treated with another equivalent of Br2, three different compounds of molecular formularole="math" localid="1648727281591" C6H4Br2 were formed.

  1. Explain why a single Kekule structure is consistent with the first result, but does not explain the second result.
  2. Then explain why a resonance description of benzene is consistent with the results of both reactions.

Question: Estimate where the protons bonded to the sp2hybridized carbons will absorb in the 1 H NMR spectrum of each compound.

Question: a. Explain why protonation of pyrrole occurs at C2 to form A, rather than on the N atom toform B.

b. Explain why A is more acidic than C, the conjugate acid of pyridine.

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).
See all solutions

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