ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Question
Chapter 17, Problem 17.1P
Interpretation Introduction
Interpretation: All possible resonance structures for the antihistamine diphenhydramine are to be drawn.
Concept introduction: Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.
Expert Solution & Answer
Answer to Problem 17.1P
All possible resonance structures for the antihistamine diphenhydramine are,
Explanation of Solution
The given structure of antihistamine diphenhydramine is shown below.
Figure 1
The given structure contains oxygen and nitrogen atoms and these atoms are not conjugated with any double bond. Thus, the lone pairs of these atoms do not participate in the resonance. Hence, possible resonance structures for the antihistamine diphenhydramine are shown below.
Figure 2
Conclusion
All possible resonance structures for the antihistamine diphenhydramine are shown in Figure 2.
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Students have asked these similar questions
Understanding how substituents activate
Rank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic
aromatic substitution.
Explanation
HN
NH2
Check
X
(Choose one)
(Choose one)
(Choose one)
(Choose one)
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Identifying electron-donating and electron-withdrawing effects on benzene
For each of the substituted benzene molecules below, determine the inductive and resonance effects the substituent will have on the
benzene ring, as well as the overall electron-density of the ring compared to unsubstituted benzene.
Inductive Effects
Resonance Effects
Overall Electron-Density
Molecule
CF3
O donating
O donating
O withdrawing
O withdrawing
O no inductive effects
O no resonance effects
electron-rich
electron-deficient
O similar to benzene
CH3
O donating
O withdrawing
O no inductive effects
O donating
O withdrawing
Ono resonance effects
O electron-rich
O electron-deficient
O similar to benzene
Explanation
Check
Х
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* Hint: Think back to Chem 1 solubility rules.
Follow Up Questions for Part B
12. What impact do the following disturbances to a system at equilibrium have on k, the rate constant
for the forward reaction? Explain. (4 pts)
a) Changing the concentration of a reactant or product. (2 pts)
b) Changing the temperature of an exothermic reaction. (2 pts)
of
Chapter 17 Solutions
ORGANIC CHEMISTRY
Ch. 17 - Prob. 17.1PCh. 17 - Problem 17.2 What orbitals are used to form the...Ch. 17 - Problem-17.3. Give the IUPAC name for each...Ch. 17 - Prob. 17.4PCh. 17 - Problem-17.5 What is the structure of propofol,...Ch. 17 - Problem 17.6 What is the structure of a compound...Ch. 17 - Problem 17.7 How many NMR signals does each...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Problem 17.14 Januvia, the trade name for...Ch. 17 - Prob. 17.15PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 17 - 17.28 Draw a structure corresponding to each...Ch. 17 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 17 - Prob. 17.30PCh. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.34PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 17 - Prob. 17.37PCh. 17 - 17.38
How many electrons does C contain?
How...Ch. 17 - Prob. 17.39PCh. 17 - 17.40 Explain the observed rate of reactivity of...Ch. 17 - 17.41 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 17.42PCh. 17 - 17.43 Draw additional resonance structures for...Ch. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - 17.46 Which compound in each pair is the stronger...Ch. 17 - 17.47 Treatment of indene with forms its...Ch. 17 - Prob. 17.48PCh. 17 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 17 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - 17.53 How many signals does each compound...Ch. 17 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 17 - 17.55 Propose a structure consistent with each...Ch. 17 - 17.56 Propose a structure consistent with each...Ch. 17 - 17.57 Thymol (molecular formula ) is the major...Ch. 17 - 17.58 You have a sample of a compound of molecular...Ch. 17 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 17 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 17 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 17 - 17.62 Answer the following questions about...Ch. 17 - 17.63 Stanozolol is an anabolic steroid that...Ch. 17 - Prob. 17.64PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - Prob. 17.68PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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