tb15 - Chapter 15 - Benzene and Aromaticitv Draw structures...

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136 Chapter 15: Benzene and Aromaticity Chapter 15 - Benzene and Aromaticitv Draw structures corresponding to the names given. 1. m-fluoroniuobenzene Answer: (iF 2. p-bromoaniline Answer: Br-Q-NH2 3. a-chlorophenol Answer: ex '" I a OH 4. 3,5-dimethylbenzoic acid Answer: COzH H3~rn3 5. p-chlorobenzaldehyde Answer: 0 CI-Q-~-H
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6. l-phenyl-3-methylpentane Answer: r Provide correct IUPAC names for each of the following compounds. 7. aI3 Answer: m-nitrotoluene or l-methyl-3-nitrobenzene 8. d' Answer: (l-methylethyl) benzene or isopropylbenzene or cumene aI3 9. Answer: 1-«1 S, 3R)- 3-methylcyclohexy1)benzene 10. NH2 H2N~CH3 Answer: l-methyl-2,4-benzenediamine or 2,4-diaminotoluene Test Itemsfor McMurry's Organic Chemistry, Seventh Edition 137
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11. Ph CH2CH2CH3 \ / C=C / \ H3C Ph Answer: (E)- 2,3-diphenyl- 2-hexene For each molecule below, predict whether the molecule would be expected to show aromatic character or not. Explain your answer in each case. 12. .. (:J N I H Answer: To meet the criterion of a cyclic, planar, conjugated molecule, the oxygen and the nitrogen bearing the hydrogen must both be sp2 -hybridized. If this occurs, both heteroatoms contribute two electrons each to the pi system. This results in a total of eight pi electrons, which is not aromatic according to the Hiickel (4n + 2) Rule. 13. OH 6 0 Answer: The carbocation is sp2-hybridized, so if the oxygen is also sp2-hybridized then each atom in the cycle has a conjugated p-orbital. Each double bond contributes two pi electrons and the oxygen contributes two pi electrons, for a total of six pi electrons in the conjugated system. Therefore, this species is predicted to show aromatic character. 14. Answer: This compound, [16]annulene, appears to be a cyclic, planar, conjugated molecule with 16 pi electrons. However, 16 is not a Hiickel number, so the compound is probably not planar, and is not aromatic. 138 Chapter 15: Benzene and Aromaticity
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15. ON !(J 0 Answer: This compound has a pyridine-like nitrogen, which is Sp2- hybridized and has its lone pair of electrons in the plane of the ring. If oxygen is also Sp2 - hybridized, then it contribute two pi electrons to the cyclic, conjugated pi system for a total of six 1t-electrons. Therefore, this molecule is predicted to show aromatic character. Answer the following questions concerning sulfathiazole, below.
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tb15 - Chapter 15 - Benzene and Aromaticitv Draw structures...

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