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Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
Author: SMITH
Publisher: MCG
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Chapter 17, Problem 17.44P
Interpretation Introduction
Interpretation: An explanation for shorter bond (a) than bond (b) is to be stated.
Concept introduction: Napthalene exhibits three resonating structures, in which second resonating structure is most stable. Due to variation in double bond character, napthalene possesses different
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Hydrocarbon A possesses a signicant 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?
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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.
Chapter 17 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
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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- 2. a) Draw the structures of Perylene dianhydride, Naphthalene and Salicylic acid b) Arrange the compounds in order of increasing polarity considering the structures and Rf valuesarrow_forwardHydrocarbon A possesses a significant dipole, even though it iscomposed of only C—C and C—H bonds. Explain why the dipole arisesand use resonance structures to illustrate the direction of the dipole.Which ring is more electron rich?arrow_forwardDraw a resonance structure, complete with all formal charges and lone (unshared) electron pairs, that shows the resonance interaction of the carboxy with the para position in benzoic acid.arrow_forward
- An electrostatic potential map of calicene is shown below. a) Both the electrostatic potential map and its significant dipole moment indicate that calicene is an unusually polar hydrocarbon. Which of the dipolar resonance forms, structure A or structure B, better corresponds to the electron distribution in the molecule? Select the single best answer. b) Which one of the following structures should be stabilized by resonance to a greater extent? Select the single best answer.arrow_forwardDraw all resonance contributors for each of the following molecules or ions. Be sure to include the curved arrows thatindicate which pairs of electrons are shifted in going from one resonance structure to the next.(a) CH3NO2(b) CH3CO-2(c) CH3CHCHCH-2(the ion has two C-C single bonds)(d) C5H5N (a ring is formed by the C and N atoms, and each H is bonded to C)(e) C4H5N (a ring is formed by the C and N atoms, the N is bonded to one H, and each C is bonded to one H)arrow_forwardRizatriptan (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 reasonableresonance structures for the ve-membered ring that contains three N atoms.arrow_forward
- Determine the weakest C-H bond in each of the following compounds. (a) (b) (c) ОНarrow_forwardDefine the consequence of resonance stabilization ?arrow_forwardFor each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.(a) ethyl chloride or ethyl iodidearrow_forward
- Bromine is a larger atom than chlorine, but the equilibrium constants in Table 3.9 indicate that a chloro substituent has a greater preference for the equatorial position than does a bromo substituent. Suggest an explanation for this fact.arrow_forwardWhich of the following is true about the carbon-carbon single bond in 1,3-butadiene when compared to the carbon-carbon single bond in ethane? (A) It is shorter than the carbon-carbon single bond of ethane. (B) The single bond in 1,3-butadiene has a higher %s character than in ethane The hydrogen atoms push the carbons closer using electrocyclic forces. Both A and B. (E) None of the above.arrow_forwardWrite a molecular formula of the following structure in its most simplified form.arrow_forward
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