Question 1

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

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Question 2

In the carbon NMR, in what region of the spectrum does one typically observe carbons which are part of the aromatic ring?

Accepted Answer

A)  -10-0 ppm 
B)  40-60 ppm 
C)  80-100 ppm 
D)  120-150 ppm 
E)  200-220 ppm 
A)  -10-0 ppm 
B)  40-60 ppm 
C)  80-100 ppm 
D)  120-150 ppm 
E)  200-220 ppm

Question 3

Provide an acceptable name for the compound below.

Accepted Answer

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Question 4

Provide the structure of tropylium bromide.

Accepted Answer

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Question 5

Which of the labeled H atoms (1 -5) in the following molecule would be predicted to be the most acidic?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  5 
A)  1 
B)  2 
C)  3 
D)  4 
E)  5

Question 6

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

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Question 7

Provide an acceptable name for PhSO3H.

Accepted Answer

benzenesul

Question 8

Which sequence ranks the indicated protons in order of increasing acidity?

Accepted Answer

A)  1 < 2 < 3 
B)  2 < 3 < 1 
C)  3 < 1 < 2 
D)  3 < 2 < 1 
A)  1 < 2 < 3 
B)  2 < 3 < 1 
C)  3 < 1 < 2 
D)  3 < 2 < 1

Question 9

Classify cyclopentadienyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

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Question 10

Describe the occupied p molecular orbitals in the ground state of cyclobutadiene.

Accepted Answer

Two electrons are paired in a

Question 11

Aromatic molecules contain ________ π electrons.

Accepted Answer

A)  no 
B)  4n + 1 (with n an integer) 
C)  4n + 2 (with n an integer) 
D)  4n (with n an integer) 
E)  unpaired 
A)  no 
B)  4n + 1 (with n an integer) 
C)  4n + 2 (with n an integer) 
D)  4n (with n an integer) 
E)  unpaired

Question 12

Provide the structure of pyrimidine.

Accepted Answer

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Question 13

Which of the following compounds has the most signals in the proton-decoupled 13C NMR spectrum?

Accepted Answer

A)  o-dibromobenzene 
B)  m-dibromobenzene 
C)  p-dibromobenzene 
D)  1,3,5-tribromobenzene 
E)  1,2,3,4-tetrabromobenzene 
A)  o-dibromobenzene 
B)  m-dibromobenzene 
C)  p-dibromobenzene 
D)  1,3,5-tribromobenzene 
E)  1,2,3,4-tetrabromobenzene

Question 14

Provide the structure of indole.

Accepted Answer

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Question 15

Show how the p orbitals overlap to generate the p4* of cyclobutadiene.

Accepted Answer

Question 16

How many peaks are in the proton spin decoupled 13C NMR spectrum of the compound shown?

Accepted Answer

Question 17

Classify the following compound as aromatic, antiaromatic, or nonaromatic.

Accepted Answer

nonaromati

Question 18

Classify cyclopentadiene as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

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Question 19

Provide an acceptable name for the compound below.

Accepted Answer

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Question 20

Provide the structure of anthracene.

Accepted Answer

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Exam 16: Aromatic Compounds

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

In the carbon NMR, in what region of the spectrum does one typically observe carbons which are part of the aromatic ring?

Provide an acceptable name for the compound below.

Provide the structure of tropylium bromide.

Which of the labeled H atoms (1 -5) in the following molecule would be predicted to be the most acidic?

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Provide an acceptable name for PhSO3H.

Which sequence ranks the indicated protons in order of increasing acidity?

Classify cyclopentadienyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Describe the occupied p molecular orbitals in the ground state of cyclobutadiene.

Aromatic molecules contain ________ π electrons.

Provide the structure of pyrimidine.

Which of the following compounds has the most signals in the proton-decoupled 13C NMR spectrum?

Provide the structure of indole.

Show how the p orbitals overlap to generate the p4* of cyclobutadiene.

How many peaks are in the proton spin decoupled 13C NMR spectrum of the compound shown?

Classify the following compound as aromatic, antiaromatic, or nonaromatic.

Classify cyclopentadiene as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Provide an acceptable name for the compound below.

Provide the structure of anthracene.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Provide an acceptable name for PhSO₃H.

Which of the following compounds has the most signals in the proton-decoupled ¹³C NMR spectrum?

Show how the p orbitals overlap to generate the p₄* of cyclobutadiene.

How many peaks are in the proton spin decoupled ¹³C NMR spectrum of the compound shown?