Exam 15: Benzene and Aromaticity
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Exam 15: Benzene and Aromaticity47 Questions
Exam 16: Chemistry of Benzene: Electrophilic Aromatic Substitution30 Questions
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Exhibit 15-3
Refer to the data below to answer the following question(s).
The 1H NMR spectrum of [14]annulene at −60°C shows two signals,one at 0 ppm and one at 7.6 ppm,with an area ratio of 5:2.
-Refer to Exhibit 15-3.Is [14]annulene aromatic?
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Correct Answer:
[14]annulene contains a cyclic,conjugated pi system with 14 pi electrons (14 = 4n + 2;n = 3).It is difficult to predict,however,if the molecule is planar without making a model.The 1H NMR signal at 7.6 ppm is consistent with the presence of a ring current,which is characteristic of aromatic molecules.Thus,[14]annulene is aromatic.
Which of the following does not correctly characterize this compound represented by the molecular model shown below? Atoms other than carbon and hydrogen are labeled.
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Correct Answer:
D
Draw a picture of the π orbitals in furan (shown below).Is furan aromatic? 
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Exhibit 15-6
Consider the data below to answer the following question(s).
C9H12;1H NMR:
6.65 δ (singlet,3H)
2.25 δ (singlet,9H)
-Refer to Exhibit 15-6.Propose a structure for this compound.
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Exhibit 15-5
Consider the data below to answer the following question(s).
C9H12;1H NMR:
7.18 δ (broad singlet,5H)
2.55 δ (triplet,2H)
1.70 δ (sextet,2H)
0.9 δ (triplet,3H)
-Refer to Exhibit 15-5.Describe the signal at 7.18 δ in terms of its splitting,integration and chemical shift.
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Exhibit 15-3
Refer to the data below to answer the following question(s).
The 1H NMR spectrum of [14]annulene at −60°C shows two signals,one at 0 ppm and one at 7.6 ppm,with an area ratio of 5:2.
-Refer to Exhibit 15-3.Explain why these protons have absorption at such high fields.
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Explain in terms of MO theory,why systems with 4n + 2 π electrons are aromatic and with 4n π electrons are antiaromatic.
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Exhibit 15-3
Refer to the data below to answer the following question(s).
The 1H NMR spectrum of [14]annulene at −60°C shows two signals,one at 0 ppm and one at 7.6 ppm,with an area ratio of 5:2.
-Refer to Exhibit 15-3.Draw in the protons on the [14]annulene skeleton provided below which are responsible for the 1H NMR signal at 0 ppm. ![Exhibit 15-3 Refer to the data below to answer the following question(s). The <sup>1</sup>H NMR spectrum of [14]annulene at −60°C shows two signals,one at 0 ppm and one at 7.6 ppm,with an area ratio of 5:2. -Refer to Exhibit 15-3.Draw in the protons on the [14]annulene skeleton provided below which are responsible for the <sup>1</sup>H NMR signal at 0 ppm.](https://storage.examlex.com/TB4944/11eab917_1508_405b_99e6_4f9c43851950_TB4944_00.jpg)
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Exhibit 15-7
Consider the data below to answer the following question(s).
C7H7ClO;IR absorption at 810 cm−1
Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/
-Refer to Exhibit 15-7.Propose a structure for this compound.
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Exhibit 15-5
Consider the data below to answer the following question(s).
C9H12;1H NMR:
7.18 δ (broad singlet,5H)
2.55 δ (triplet,2H)
1.70 δ (sextet,2H)
0.9 δ (triplet,3H)
-Refer to Exhibit 15-5.Propose a structure for this compound.
(Essay)
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Exhibit 15-7
Consider the data below to answer the following question(s).
C7H7ClO;IR absorption at 810 cm−1
Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/
-Refer to Exhibit 15-7.Calculate the degrees of unsaturation for this compound.
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Exhibit 15-7
Consider the data below to answer the following question(s).
C7H7ClO;IR absorption at 810 cm−1
Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/
-Refer to Exhibit 15-7.Describe the signal at 3.7 δ in terms of its splitting,integration and chemical shift.
(Essay)
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Exhibit 15-5
Consider the data below to answer the following question(s).
C9H12;1H NMR:
7.18 δ (broad singlet,5H)
2.55 δ (triplet,2H)
1.70 δ (sextet,2H)
0.9 δ (triplet,3H)
-Refer to Exhibit 15-5.Describe the signal at 2.55 δ in terms of its splitting,integration,and chemical shift.
(Essay)
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