Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 15, Problem 57P
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
rizatriptan
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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 reasonableresonance structures for the ve-membered ring that contains three N atoms.
Draw all of the resonance structures for each of the following species. Be sure to include the curved arrows that indicate
which pairs of electrons are shifted in going from one resonance structure to the next. Draw the resonance hybrid of
each species.
(a)
ОН
(b)
(c)
H3C
The curved arrow notation introduced in Section 1.6B is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions.Because each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.
Chapter 15 Solutions
Organic Chemistry (6th Edition)
Ch. 15.2 - Prob. 1PCh. 15.2 - Problem 17.2 What orbitals are used to form the...Ch. 15.3 - Prob. 4PCh. 15.3 - Problem-17.5 What is the structure of propofol,...Ch. 15.6 - Prob. 7PCh. 15.8 - Prob. 8PCh. 15.8 - Prob. 11PCh. 15.8 - Prob. 12PCh. 15.8 - Problem 17.16 Rank the following compounds in...Ch. 15.8 - Problem 17.17 Draw the seven resonance structures...
Ch. 15 - 17.23 Name each compound and state how many lines...Ch. 15 - Prob. 21PCh. 15 - Prob. 22PCh. 15 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 15 - 17.28 Draw a structure corresponding to each...Ch. 15 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - 17.38
How many electrons does C contain?
How...Ch. 15 - Prob. 36PCh. 15 - 17.40 Explain the observed rate of reactivity of...Ch. 15 - 17.41 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 39PCh. 15 - 17.43 Draw additional resonance structures for...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 17.46 Which compound in each pair is the stronger...Ch. 15 - 17.47 Treatment of indene with forms its...Ch. 15 - Prob. 45PCh. 15 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 15 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 15 - Prob. 48PCh. 15 - Prob. 49PCh. 15 - 17.53 How many signals does each compound...Ch. 15 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 15 - 17.55 Propose a structure consistent with each...Ch. 15 - 17.56 Propose a structure consistent with each...Ch. 15 - 17.57 Thymol (molecular formula ) is the major...Ch. 15 - 17.58 You have a sample of a compound of molecular...Ch. 15 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 15 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 15 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 15 - 17.62 Answer the following questions about...Ch. 15 - 17.63 Stanozolol is an anabolic steroid that...Ch. 15 - Prob. 61P
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- (a) Label each carbon, oxygen, and nitrogen atom as being sp, sp, or sp' hybridized. (b) Circle and identify each functional group by its formal name. (c) Redraw the following compound to be a complete Lewis structure, showing all carbons, hydrogens, bonds, and nonbonded electrons. yo NECarrow_forwardThe curved arrow notation introduced in Section 1.6B is a powerfulmethod used by organic chemists to show the movement of electronsnot only in resonance structures, but also in chemical reactions.Because each curved arrow shows the movement of two electrons,following the curved arrows illustrates what bonds are broken andformed in a reaction. Consider the following three-step process. (a) Addcurved arrows in Step [1] to show the movement of electrons. (b) Use thecurved arrows drawn in Step [2] to identify the structure of X. X isconverted in Step [3] to phenol and HCl.arrow_forwardCreatine is a dietary supplement used by some athletes to boost their athletic performance. (a) Draw in all lone pairs in creatine. (b) Draw two additional resonance structures showing all lone pairs and formal charges.arrow_forward
- (a) Draw all resonance contributors of the following ion. In drawing each additional resonance structure, use curved arrows to indicate which pairs of electrons are being shifted. (b) Draw the resonance hybrid. (c) Which c–C bond is the longest?arrow_forwardConsider Lewis formulas A, B, and C:(a) Are A, B, and C constitutional isomers, or are they resonance contributors? (b) Which have a negatively charged carbon? (c) Which have a positively charged carbon? (d) Which have a positively charged nitrogen? (e) Which have a negatively charged nitrogen? (f) What is the net charge on each? (g) Which is a more stable structure, A or B? Why? (h) Which is a more stable structure, B or C? Why? (i) What is the CNN geometry in each according to VSEPR?arrow_forwardCreatine is a dietary supplement used by some athletes to boost theirathletic performance. (a) Draw in all lone pairs in creatine. (b) Draw two additional resonance structures showing all lone pairs and formal charges.arrow_forward
- 1. (a) Redraw the following compound to be a complete Lewis structure, showing all carbons, hydrogens, bonds, and nonbonded electrons. (b) Label each carbon, oxygen, and nitrogen ator being sp, sp', or sp' hybridized. (c) Circle and identify each functional group by its formal name.arrow_forwardThe following questions are regarding the structure of oseltamivir (Tamiflu) antiviral medication used to treat and prevent influenza. a.) How many hydrogens are there in Tamiflu? (b) What is the molecular weight of Tamilfu? (c) How many π bonds does Tamiflu contain? (d) List all functional groups contained in Tamilfu.arrow_forwardThe curved arrow notation introduced in Section 1.6 is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions. Since each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.arrow_forward
- 16. Which of the following structures is the CORRECT resonance structure of the following. molecule: (A) (B) (C) (D) CH3- CH₂ CH3 -H CH₂CH3 CH₂CH-CH₂ CH3 CH3arrow_forwardJanuvia, the trade name for sitagliptin, was introduced in 2006 for the treatment of type 2 diabetes. (a) Explain why the five-membered ring in sitagliptin is aromatic. (b) Determine the hybridization of each N atom. (c) In what type of orbital does the lone pair on each N atom reside?arrow_forwardCompute the formal charge (FC) on each atom in the following structures. (b) The hydronium ion, H3O+arrow_forward
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