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Chapter 17: Q.43. (page 641)

Question: Draw additional resonance structures for each species.

Short Answer

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Answer

a.

b.

c.

Step by step solution

01

Resonance structures

Several structures can be employed to detail bonding in a particular molecule, and such structures are resonance structures. Another name that is employed to denote resonance structures is canonical structures.

02

Cyclic compounds

Cyclic compounds are compounds where one or several atoms are connected like a ring. There are several cyclic compounds, and some of them include cyclopropane and cyclohexane.

03

Additional resonance structures for each species

a. The additional resonance structures of cyclopropenyl radical can be given as:

Additional resonance structure of cyclopropenyl radical

b. The additional resonance structures of pyrrole can be given as:

Additional resonance structures of pyrrole

c. The additional resonance structures of phenanthrene can be given as:

Additional resonance structures of phenanthrene

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Most popular questions from this chapter

Question: Methotrexate, a drug that inhibits the metabolism of folic acid, is used in the treatment of a variety of cancers and autoimmune disorders such as rheumatoid arthritis. (a) Give the hybridization of each N atom in methotrexate. (b) In what type of orbital does the lone pair of each N reside? (c) Explain why the bicyclic ring system that contains four N atoms is aromatic.

Question: Considering both 5-methylcyclopenta-1,3-diene (A) and 7-methylcyclohepta-1,3,5-triene (B), which labeled H atom is most acidic? Which labeled H atom is least acidic? Explain your choices.

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: Thymol (molecular formula C10H14O) is the major component of the oil of thyme. Thymol shows IR absorptions at 3500鈥�3200, 3150鈥�2850, 1621, and 1585 localid="1648806094089" cm-1. The H1NMR spectrum of thymol is given below. Propose a possible structure for thymol.

Question: Zolpidem (trade name Ambien) promotes the rapid onset of sleep, making it a widely prescribed drug for treating insomnia.

a. In what type of orbital does the lone pair on each N atom in the heterocycle reside?

b. Explain why the bicyclic ring system that contains both N atoms is aromatic.

c. Draw all reasonable resonance structures for the bicyclic ring system.
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