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Chapter 17: Q.1. (page 641)

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

Short Answer

Expert verified

Answer

Resonating structures of diphenhydramine.

Step by step solution

01

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 πbond 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

Draw the structure corresponding to each name

  1. isobutyl benzene
  2. o-dichlorobenzene
  3. cis-1,2-diphenylcyclohexane
  4. m-bromoaniline
  5. 4-chloro-1,2-diethylbenzene
  6. 3-tert-butyl-2-ethyltoluene

Question: Propose a structure consistent with each set of data.

a. Compound A:

Molecular formula: C8H10O

IR absorption at role="math" localid="1648804967273" 3150-2850cm-1

H1NMR data: 1.4 (triplet, 3 H), 3.95 (quartet, 2 H), and 6.8–7.3 (multiplet, 5 H) ppm

b. Compound B:

Molecular formula: C9H10O2

IR absorption at role="math" localid="1648805107903" 1669cm-1

H1NMR data: 2.5 (singlet, 3 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.9 (doublet, 2 H) ppm

Question: Draw the seven resonance structures for the tropyllium cation.

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

Question: Propose a structure consistent with each set of data.

a. C10H14: IR absorptions at 3150-2850,1600, and 1500cm-1

b. C9H12: C13NMR signals at 21, 127, and 138 ppm

c. C8H10: IR absorptions at 3108-2875cm-1, 1606, and 1496cm-1
See all solutions

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