Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 16, Problem 16.33SP
Azulene is a deep-blue hydrocarbon with resonance energy of 205 kJ/mol (49 kcal/mol). Azulene has ten pi electrons, so it might be considered as one large
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3) In the mid-1930s, the German theoretical chemist Erich Hückel developed a rule that dealt with the aromaticity of various compounds, which became known as the Hückel Rule. Which (parts) of the compounds listed below are aromatic? Justify your answer based on Hückel's rule. You can treat the rings separately or together as you wish.image iv: colchicine: a highly poisonous alkaloid,obtained from autumn turmeric and used to treat gout.
The compound shown reacts readily with HBr and adds water across at least of one of its double bonds. Why doesn't it
behave like Benzene?
1. It is NOT a 4n + 2 system
2. severe steric interactions prevent it from being flat
3. It does NOT have a continous array of p orbitals to overlap
4. There are too many pi bonds to be aromatic
(b) The structure of heptalene (2E) is shown below. Answer the following questions: (i) Is
heptalene aromatic, non-aromatic, or anti-aromatic? (ii) 2E can be readily protonated to
form a more stable species. Draw the structure of the protonated 2E and explain the
stability.
heptalene (2E)
Chapter 16 Solutions
Organic Chemistry (9th Edition)
Ch. 16.2 - Prob. 16.1PCh. 16.2 - Prob. 16.2PCh. 16.2 - a. Draw the resonance forms of benzene,...Ch. 16.2 - Show the product of the Diels-Alder dimerization...Ch. 16.4 - Prob. 16.5PCh. 16.6 - Make a model of cyclooctatetraene in the tub...Ch. 16.6 - Prob. 16.7PCh. 16.6 - Prob. 16.8PCh. 16.7 - Prob. 16.9PCh. 16.8A - a. Draw the molecular orbitals for the...
Ch. 16.8A - Repeat Problem16-10 for the cyclopentadienyl ions....Ch. 16.8C - Explain why each compound or ion should be...Ch. 16.8C - The following hydrocarbon has an unusually large...Ch. 16.8C - Prob. 16.14PCh. 16.8C - Prob. 16.15PCh. 16.9B - Prob. 16.16PCh. 16.9C - Show which of the nitrogen atoms in purine are...Ch. 16.9C - The proton NMR spectrum of 2-pyridone gives the...Ch. 16.9D - Prob. 16.19PCh. 16.9D - Prob. 16.20PCh. 16.10 - Prob. 16.21PCh. 16.12 - Ciprofloxacin is a member of the fluoroquinolone...Ch. 16.13 - Draw and name all the chlorinated benzenes having...Ch. 16.13 - Name the following compounds:Ch. 16.15 - The UV spectrum of 1-phenylprop-2-en-1-ol shows an...Ch. 16 - Prob. 16.26SPCh. 16 - Name the following compounds:Ch. 16 - Draw and name all the methyl, dimethyl, and...Ch. 16 - Four pairs of compounds are shown. In each pair,...Ch. 16 - One of the following hydrocarbons is much more...Ch. 16 - In Kekuls time cyclohexane was unknown, and there...Ch. 16 - Prob. 16.32SPCh. 16 - Azulene is a deep-blue hydrocarbon with resonance...Ch. 16 - Prob. 16.34SPCh. 16 - Prob. 16.35SPCh. 16 - Prob. 16.36SPCh. 16 - Prob. 16.37SPCh. 16 - Prob. 16.38SPCh. 16 - Prob. 16.39SPCh. 16 - Biphenyl has the following structure. a. Is...Ch. 16 - Anions of hydrocarbons are rare, and dianions of...Ch. 16 - How would you convert the following compounds to...Ch. 16 - Prob. 16.43SPCh. 16 - Prob. 16.44SPCh. 16 - A student found an old bottle labeled thymol on...Ch. 16 - Prob. 16.46SPCh. 16 - Prob. 16.47SPCh. 16 - Prob. 16.48SPCh. 16 - The proton NMR chemical shifts of the hydrogens in...Ch. 16 - Prob. 16.50SPCh. 16 - NMR has been used to probe many molecular...
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- (b) The activating and deactivating groups could affect the position(s) of the next incoming group(s) to the benzene ring. Based on the structure below, analyze and explain the group(s) on the benzene ring is activating or deactivating group. Then, identify the product(s) formed from the following reactions. NH, CC, CH;CH,COCI AICI, (i) NH, HNO, H,SO, (ii) H Br AICI, (iii) Page 3 of 4arrow_forwardDetermine the class of the compound, which contains only carbon and hydrogen, and exhibits the infrared spectrum below. Possible compound classes are:alkane, alkene, alkyne, aromatic, alcohol, amine, aldehydeketone, carboxylic acid, acid chloride, ester, amide Chem 1 = Chem 2 image=arrow_forwardCH=CHNO₂ (2-nitrovinyl)benzene Electrophilic substitution on (2-nitrovinyl)benzene occurs at the meta position. Draw resonance structures to show how the ring is electron-poor at the ortho and para positions. You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu. 0 78 00-F karrow_forward
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