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Chapter 17: Problem 17.1 (page 644)

Draw all possible resonance structures for the antihistamine diphenhydramine, the active ingredient in Benadryl.

Short Answer

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Answer

Resonating structures of diphenhydramine.

Step by step solution

01

Step-by-Step Solution Step 1: Resonance structures

Some properties of an organic compound, that cannot be explained by a single structure are explained using multiple structures.

That differs only in the position of bond or nonbonding electrons are called resonance or canonical structures.

02

Resonance structures for diphenhydramine

Resonating structures are drawn by only moving the 蟺bonds (atoms or groups never change their position).

Resonance structures for diphenhydramine

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Most popular questions from this chapter

Question: Which compounds are aromatic? For any compound that is not aromatic, state why this is so.

Question: Explain why compound A is much more stable than compound B.

Question: Draw the conjugate bases of pyrrole and cyclopentadiene. Explain why thesp3 hybridized C-H bond of cyclopentadiene is more acidic than the N-H bond of pyrrole.

Question: Use the inscribed polygon method to show the pattern of molecular orbitals in cyclooctatetraene.

a. Label the MOs as bonding, antibonding, or nonbonding.

b. Indicate the arrangement of electrons in these orbitals for cyclooctatetraene, and explain why cyclooctatetraene is not aromatic.

c. Treatment of cyclooctatetraene with potassium forms a dianion. How many蟺electrons does this dianion contain?

d. How are the 蟺electrons in this dianion arranged in the molecular orbitals?

e. Classify the dianion of cyclooctatetraene as aromatic, antiaromatic, or not aromatic, and explain why this is so.

Question: Draw the four resonance structures for anthracene.
See all solutions

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