ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Textbook Question
Chapter 16, Problem 16.40SP
Biphenyl has the following structure.
- a. Is biphenyl a (fused) polynuclear aromatic hydrocarbon?
- b. How many pi electrons are there in the two aromatic rings of biphenyl? How does this number compare with that for naphthalene?
- c. The heat of hydrogenation for biphenyl is about 418 kJ/mol (100 kcal/mol). Calculate the resonance energy of biphenyl.
- d. Compare the resonance energy of biphenyl with that of naphthalene and with that of two benzene rings. Explain the difference in the resonance energies of naphthalene and biphenyl.
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1. Explain the following
- why stearic acid has higher melting point than decanoic acid.
- why benzoic acid has higher melting point than stearic acid.
- why salicylic acid has higher melting point than benzoic acid.
- why octane has a higher melting point than isooctane.
- why 2,2,3,3-tetramethylbutane has the highest melting point among the three isomers of C8H18.
Benzene’s unusual properties is not limited to hydrogenation. Which one is true about reaction of benzene with Br2?
I. Does not undergo addition reactions typical of other highly unsaturated compounds
II. Benzene does not react with Br2 to yield addition product
III. In the presence of a Lewis acid, bromine substitutes for a hydrogen atom yielding a substitution product
IV. A substitution product still contains a benzene ring
Chapter 16 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
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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