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Exam 18: Aromatic Compounds

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Question 1

Multiple Choice

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Which of the following annulenes is not aromatic?

A) [6]-Annulene
B) [14]-annulene
C) [16]-annulene
D) [18]-annulene
E) [22]-annulene

F) A) and C)
G) A) and B)

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Question 2

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What is the structure for styrene?

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11eab459_a5be_42d8_acdb_1755b80ffdd1_TB3185_00

Question 3

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What is the IUPAC name for the following compound?

Which of the following structures with molecular formula C₈H₉Br, is consistent with the following ¹H NMR spectrum. ¹H NMR: 2.8 $\delta$ (triplet, I=2H) , 4.65 $\delta$ (triplet, I=2H) , 7.2 $\delta$ (multiplet, I=5H)

Provide the product for the following reaction? Explain your answer.

What is the IUPAC name for the following compound?

The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers are difficult to distinguish using ¹H NMR, but they can be easily identified using ¹³C NMR. Describe how ¹³C NMR distinguishes these three isomers.

Which one of the following compounds would exhibit seven signals in its ¹³C NMR spectrum?

What is the IUPAC name for the following compound?

Using a Frost circle, draw the molecular orbital energy diagram for the cyclopentadienyl anion and predict if it is aromatic.

Provide the reagents necessary to convert ethylbenzene to styrene.

What is the correct structure for 4-amino-2-chlorophenol?

A compound with molecular formula C₉H₁₂O displays the following ¹H NMR and ¹³C NMR spectra. Propose a structure for this compound.

According to the molecular orbital theory how many molecular orbitals are formed when the six p-orbitals of benzene combine?

Which one of the following compound is aromatic?

Provide the reagents necessary to carry out the following conversion.

Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Provide the structure of the major product(s) for the following reaction.

Which one of the following compound(s) is antiaromatic?

Using a Frost circle, draw the molecular orbital energy diagram for the cyclopropenyl anion and predict if it is aromatic.