Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 17, Problem 17.39P
Interpretation Introduction
Interpretation: The reason corresponding to the fact that AZT is aromatic is to be explained.
Concept introduction: A molecule must be cyclic, planar, completely conjugated and should follow
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Serotonin 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:
Which best explains why the bromination of
nitrobenzene is slower than the bromination of
benzene?
A)
B)
C)
D)
The -NO₂ group stabilizes the cationic
intermediate by induction
The -NO₂ group stabilizes the cationic
intermediate by resonance
The -NO₂ group destabilizes the
anionic intermediate by induction
The -NO₂ group destabilizes the
cationic intermediate by resonance and
induction
AZT was the first drug approved to treat HIV, the virus that causes AIDS. Explain why the sixmembered ring of AZT is aromatic.
Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Prob. 17.1PCh. 17 - What orbitals are used to form the bonds indicated...Ch. 17 - Give the IUPAC name for each compound.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 - How many 13C NMR signals does each compound...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 - Prob. 17.16PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - Prob. 17.27PCh. 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. 17.31PCh. 17 - Prob. 17.32PCh. 17 - Prob. 17.33PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.35PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 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 - 17.61 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. 17.63PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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- If a molecule contains an aromatic ring, such as a benzene ring, attached to a non-aromatic ring, how does that affect the overall aromaticity of the molecule?arrow_forwarda) Which molecule has a higher electron density in the aromatic ring? Explain. H₂C O CO₂H CO₂H H₂C-N CH3 CH3 b) which is more acidic?arrow_forwardAnswer the following questions for the non-aromatic compound. 1. is every compound cyclic? yes or no 2. is every compound conjugated? yes or no 3. is every atom with a p-orbital connected to atoms on both sides that have a p-orbital? yes or no 4. based on the orbital drawings, are all p-orbitals in the same plane? yes or noarrow_forward
- AZT was the rst drug approved to treat HIV, the virus that causes AIDS. Explain why the sixmembered ring of AZT is aromatic.arrow_forward2. 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_forwardAnswer the following questions for the aromatic compound. 1. is every compound cyclic? yes or no 2. is every compound conjugated? yes or no 3. is every atom with a p-orbital connected to atoms on both sides that have a p-orbital? yes or no 4. Are all p-orbitals in the same plane? yes or noarrow_forward
- Pyrene has been determined experimentally to be aromatic. At first glance, however, its structure appears to break Hückel’s rule. How so? Can you explain why pyrene exhibits aromaticity?Hint: What are the characteristics of the π system on the periphery of the molecule?arrow_forwardWhich of the following is NOT a criterion for a molecule to exhibit aromatic stabilization? O planarity of the molecule O (4n+2) conjugated n-electrons O molecule cannot have a positive or negative charge O molecule must be cyclic O all atoms in question must have a p orbitalarrow_forwardWhich contributes to the π aromatic system?arrow_forward
- Cycloheptatriene is not considered to be an aromatic compound because it does not satisfy the aromaticity rules. However when it loses a hydride ion as shown below, it is said to be an aromatic compound. Explain why this is so: H H Harrow_forwardA bicyclic heterocycle aromatic ring with one N atom and the rings are of different size. a Indole b Pyrazine c Purine d Quinolinearrow_forwardClick the "draw structure" button to launch the drawing utility. Under certain reaction conditions, 2,3-dibromobutane reacts with two equivalents of base to give three products, each of which contains two new T bonds. Product A has two sp hybridized carbon atoms, product B has one sp hybridized carbon atom, and product C has none. What is the structure of C?arrow_forward
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