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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: Hydrocarbon A possesses a significant dipole, even though it is composed of only C-C and C-H bonds. Explain why the dipole arises and use resonance structures to illustrate the direction of the dipole. Which ring is more electron rich?

Question: Although benzene itself absorbs at 128 ppm in its C13NMR spectrum, the carbons of substituted benzenes absorb either upfield or downfield from this value depending on the substituent. Explain the observed values for the carbon ortho to the given substituent in the monosubstituted benzene derivatives X and Y.

Question: Name each compound and state how many lines are observed in its C13NMR spectrum.

Question:

a. How many 蟺electrons does C contain?

b. How many 蟺electrons are delocalized in the ring?

c. Explain why C is aromatic.

Question: Draw a structure corresponding to each name.

  1. p-dichlorobenzene
  2. p-iodoaniline
  3. o-bromonitrobenzene
  4. 2,6-dimethoxytoluene
  5. 2-phenylprop-2-en-1-ol
  6. trans-1-benzyl-3-phenylcyclopentane
See all solutions

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