ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 15, Problem 58P
Zolpidem (trade name Ambien) promotes the rapid onset of sleep, making it a widely prescribed drug for treating insomnia.
a In what type of orbital does the lone pair on each N atom in the heterocycle reside?
b. Explain why the bicyclic ring system that contains both N atoms is
c. Draw all reasonable resonance structures for the bicyclic ring system.
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Chapter 15 Solutions
ORGANIC CHEMISTRY
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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- 2. Nicotine contains two heterocyclic rings. a) Fill in the blanks regarding the N atom of each ring. b) Circle the ring that is aromatic and explain what makes it aromatic. hybridization of N: orbital of lone pair: H nicotine hybridization of N: orbital of lone pair:arrow_forwardWhich of the following statements is incorrect: aromatic compounds... a. Are cyclic b. Are generally less reactive than similarly substituted alkenes c. Are planar O d. Have 4n n-electrons Benzene or the other aromatic species all have high "pi" electron density inside the aromatic ring. Select one: True O Falsearrow_forward1. Draw the structure for each compound. a.(3R)-3-methylhexane b. (3R,5S,6R)-5-ethyl-3,6-dimethylnonanearrow_forward
- 1. Which of the following structures is considered aromatic?arrow_forwardquestion 6. Which of the following is anti-aromatic?arrow_forwardSerotonin contains an aromatic heterocycle called an indole. a) Fill in the blanks regarding the N atom of the indole. b) Circle the entire aromatic heterocycle and explain what makes it aromatic. НО. serotonin NH₂ hybridization of N: orbital of lone pair:arrow_forward
- Groups that withdraw electrons from the ring decrease the electron density of the ring, increasing the ring reactivity. Is that true or false?arrow_forward4. a) Explain why pyrrole is aromatic. Draw an orbital energy diagram (arrows on lines) that indicates where the non-bonding electron pair in nitrogen is located. H furan b) Furan can undergo electrophilic aromatic substitution, just like benzene. Draw the intermediate and its resonance form(s) if furan is substituted with an electrophile (E') in the C-2 position. c) Draw the intermediate and its resonance form(s) if furan is substituted with an electrophile (E") in the C-3 position. d) Based upon your answers to b and c, what is the product of the following reaction. HNO3 H₂SO4 €arrow_forwardThe following is generic depiction of a reaction using the curve arrow formalism. -D Which of these statements is not correct for this reaction? Electrons move from C to B. Electrons move from B to A. O In the products, a bond forms between C and B. O In the products, A would have a positive charge.arrow_forward
- Which of the following molecules is non-aromatic?A. 1,3,5-cycloheptatrienyl cation B. 1.3-cyclopentadienyl anion C. 1.3.5-cycloheptatrienyl anion D. 1.3.5.7-cyclooctatetraene E. 1.3.5-cycloheptatrienearrow_forwardA bicyclic heterocycle aromatic ring with four N atoms. a Pyridine b Pyrazine c Purine d Pyrrolearrow_forward44 How many double bonds would be in one of the resonance structure of aromatic napthalene? a. c. b. 6 d. 12arrow_forward
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