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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: 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: Would [16]-, [20]- or [22]-annulene be aromatic if each ring is planar?

Question: Use the inscribed polygon method to show why the cyclopentadienyl cation and radical are not aromatic.

Question: Answer the following questions about curcumin, a yellow pigment isolated from turmeric, a tropical perennial in the ginger family and a principal ingredient in curry powder.

a. In Chapter 11 we learned that most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols.

b. Explain why the enol O-H proton is more acidic than an alcohol O-H proton.

c. Why is curcumin colored?

d. Explain why curcumin is an antioxidant.

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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