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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 πbonds (atoms or groups never change their position).

Resonance structures for diphenhydramine

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Most popular questions from this chapter

Question: AZT was the first drug approved to treat HIV, the virus that causes AIDS. Explain why the six-membered ring of AZT is aromatic.

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: The purine heterocycle occurs commonly in the structure of DNA.

a. How is each N atom hybridized?

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

c. How many πelectrons does purine contain?

d. Why is purine aromatic?

Question: Rizatriptan (trade name Maxalt) is a prescription drug used for the treatment of migraines.

a. How many aromatic rings does rizatriptan contain?

b. Determine the hybridization of each N atom.

c. In what type of orbital does the lone pair on each N reside?

d. Draw all the resonance structures for rizatriptan that contain only neutral atoms.

e. Draw all reasonable resonance structures for the five-membered ring that contains three N atoms.

Question: Treatment of indene with NaNH2forms its conjugate base in a Brønsted–Lowry acid-base reaction. Draw all reasonable resonance structures for indene’s conjugate base, and explain why the pKaof indene is lower than the pKaof most hydrocarbons.
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