Question 1

Explain the relative acidities of cyclohexene (pKa of 46) and cyclopentadiene (pKa of 16).

Accepted Answer

The conjugate base o

Question 2

Provide the structure of pyrimidine.

Accepted Answer

The answer of Provide the structure of pyrimidine....

Question 3

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 4

Provide the structure of anthracene.

Accepted Answer

The answer of Provide the structure of anthracene....

Question 5

How many pairs of degenerate π molecular orbitals are found in benzene?

Accepted Answer

A)  6 
B)  5 
C)  4 
D)  3 
E)  2 
A)  6 
B)  5 
C)  4 
D)  3 
E)  2

Question 6

The IR spectrum of m-xylene contains stretches which are characteristic of most aromatic hydrocarbons. List the peaks (in cm-1) associated with the aromatic C   
C stretch and the aromatic C-H stretch.

Accepted Answer

C @#IMG-DLM& C: around 1600 cm

Question 7

Provide an acceptable name for the compound below.

Accepted Answer

1,3,5-trin

Question 8

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

Accepted Answer

The answer of Classify cycloheptatrienyl cation as aromatic, antiaromatic, or...

Question 9

Styrene (shown below) has 8 π electrons but is aromatic. Why?

Accepted Answer

Only 6 π electrons a

Question 10

Which orbital is the lone pair of each N in, sp2 or p?

Accepted Answer

Question 11

Use the polygon rule to draw the MO energy diagram of the cyclononatetraenyl anion. Assuming planarity, would this ion be aromatic or antiaromatic?

Accepted Answer

The answer of Use the polygon rule to draw the...

Question 12

Provide the major resonance structures of the ion which results when the most acidic hydrogen of cyclopentadiene is lost.

Accepted Answer

The answer of Provide the major resonance structures of the...

Question 13

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

Accepted Answer

The answer of Classify the following compound as aromatic, antiaromatic,...

Question 14

Provide an acceptable name for the compound below.

Accepted Answer

The answer of Provide an acceptable name for the compound...

Question 15

Provide the structure of p-aminobenzoic acid.

Accepted Answer

The answer of Provide the structure of p-aminobenzoic acid....

Question 16

In the 13C 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 17

Pyrene has been tentatively identified in the interstellar medium. Use Huckel Rule to determine is pyrene is aromatic or antiaromatic (assuming planarity of the π system).

Accepted Answer

If you consider only the π ele

Question 18

Name two of the three common allotropes of carbon.

Accepted Answer

diamond; graphite; f

Question 19

Provide a correct common name for the following compound.

Accepted Answer

p-acetylbe

Question 20

How many distinct trichlorobenzene isomers are possible?

Accepted Answer

A)  2 
B)  3 
C)  4 
D)  5 
E)  6 
A)  2 
B)  3 
C)  4 
D)  5 
E)  6

Exam 16: Aromatic Compounds

Explain the relative acidities of cyclohexene (pKa of 46) and cyclopentadiene (pKa of 16).

Provide the structure of pyrimidine.

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

Provide the structure of anthracene.

How many pairs of degenerate π molecular orbitals are found in benzene?

The IR spectrum of m-xylene contains stretches which are characteristic of most aromatic hydrocarbons. List the peaks (in cm-1) associated with the aromatic C C stretch and the aromatic C-H stretch.

Provide an acceptable name for the compound below.

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

Styrene (shown below) has 8 π electrons but is aromatic. Why?

Which orbital is the lone pair of each N in, sp2 or p?

Use the polygon rule to draw the MO energy diagram of the cyclononatetraenyl anion. Assuming planarity, would this ion be aromatic or antiaromatic?

Provide the major resonance structures of the ion which results when the most acidic hydrogen of cyclopentadiene is lost.

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

Provide an acceptable name for the compound below.

Provide the structure of p-aminobenzoic acid.

In the 13C NMR, in what region of the spectrum does one typically observe carbons which are part of the aromatic ring?

Pyrene has been tentatively identified in the interstellar medium. Use Huckel Rule to determine is pyrene is aromatic or antiaromatic (assuming planarity of the π system).

Name two of the three common allotropes of carbon.

Provide a correct common name for the following compound.

How many distinct trichlorobenzene isomers are possible?

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

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

Explain the relative acidities of cyclohexene (pK_a of 46) and cyclopentadiene (pK_a of 16).

The IR spectrum of m-xylene contains stretches which are characteristic of most aromatic hydrocarbons. List the peaks (in cm^-1) associated with the aromatic C C stretch and the aromatic C-H stretch.

Which orbital is the lone pair of each N in, sp² or p?

In the ¹³C NMR, in what region of the spectrum does one typically observe carbons which are part of the aromatic ring?