Question 1

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

Accepted Answer

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

Question 2

What is the IUPAC name of the following compound?

Accepted Answer

A) 1-bromo-2-fluoro-4-toluene 
B) 4-bromo-2-fluorotoluene 
C) 2-bromo-4-fluorophenol 
D) 4-bromo-2-fluoroxylene 
A) 1-bromo-2-fluoro-4-toluene 
B) 4-bromo-2-fluorotoluene 
C) 2-bromo-4-fluorophenol 
D) 4-bromo-2-fluoroxylene

Question 3

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 4

What is the IUPAC name of the following compound?

Accepted Answer

The answer of What is the IUPAC name of the...

Question 5

What is the hybridization of the oxygen atom of furan?

Accepted Answer

A) s 
B) sp 
C) sp2 
D) sp3 
A) s 
B) sp 
C) sp2 
D) sp3

Question 6

Consider the following structure.   The S1U1P11S1S1P0H NMR spectrum of [14]annulene at -60S1U1P1$\circ$S1S1P0C shows two peaks, one at 0 ppm and one at 7.6 ppm.
-The NMR data would seem to indicate that this compound is ____________.

Accepted Answer

The answer of Consider the following structure.   The...

Question 7

Which of the following statements is not true about the structure of benzene?

Accepted Answer

A) the carbon-carbon bonds are all the same length 
B) the structure rapidly transforms between two resonance contributors 
C) the structure is an average of two resonance contributors 
D) the ring of six carbon atoms is planar 
A) the carbon-carbon bonds are all the same length 
B) the structure rapidly transforms between two resonance contributors 
C) the structure is an average of two resonance contributors 
D) the ring of six carbon atoms is planar

Question 8

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

Accepted Answer

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

Question 9

The following compound is named (Z)-2,3-diphenyl-2-hexene.

Accepted Answer

A) True 
 B)False

Question 10

What are the relative positions of the substituents in the following structure?

Accepted Answer

A) anti 
B) meta 
C) ortho 
D) para 
A) anti 
B) meta 
C) ortho 
D) para

Question 11

What is the intermediate in the reaction of ethylbenzene with NBS in the presence of benzoyl peroxide to give 1-bromo-1-phenylethane?

Accepted Answer

A) Benzylic anion 
B) Benzylic cation 
C) Benzylic radical 
D) Benzylic carbene 
A) Benzylic anion 
B) Benzylic cation 
C) Benzylic radical 
D) Benzylic carbene

Question 12

Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene?

Accepted Answer

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

Question 13

What is the best choice of reagent to achieve the following reaction?

Accepted Answer

A) Br2, CCl4 
B) HBr, H2O 
C) Br2, light 
D) NaBr 
A) Br2, CCl4 
B) HBr, H2O 
C) Br2, light 
D) NaBr

Question 14

Consider the following structure.  
-Using the Hückel criteria, the compound would be ______________.

Accepted Answer

The answer of Consider the following structure.  
-Using the...

Question 15

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 16

Provide a brief explanation of why the cyclopentadienyl anion (below) is aromatic. Your answer should identify the hybridization of each carbon atom and account for which electrons are in the pi system.

Accepted Answer

The all five carbons are sp² hybridized.

Question 17

Which of the following compounds is aromatic?

Accepted Answer

A) ethane 
B) cyclobutadiene 
C) benzene 
D) cyclooctatetraene 
A) ethane 
B) cyclobutadiene 
C) benzene 
D) cyclooctatetraene

Question 18

Which of the following does not undergo oxidation in the presence of H2CrO4?

Accepted Answer

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

Question 19

What is the IUPAC name of the following compound?

Accepted Answer

4-chloro-3

Question 20

The product of the following reaction would be 1-bromo-1-phenylethane.

Accepted Answer

A) True 
 B)False

Exam 21: Benzene and the Concept of Aromaticity

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

What is the IUPAC name of the following compound?

What is the major organic product obtained from the following reaction?

What is the IUPAC name of the following compound?

What is the hybridization of the oxygen atom of furan?

Consider the following structure. The 1H NMR spectrum of [14]annulene at -60 ∘\circ∘ C shows two peaks, one at 0 ppm and one at 7.6 ppm. -The NMR data would seem to indicate that this compound is ____________.

Which of the following statements is not true about the structure of benzene?

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

The following compound is named (Z)-2,3-diphenyl-2-hexene.

What are the relative positions of the substituents in the following structure?

What is the intermediate in the reaction of ethylbenzene with NBS in the presence of benzoyl peroxide to give 1-bromo-1-phenylethane?

Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene?

What is the best choice of reagent to achieve the following reaction?

Consider the following structure. -Using the Hückel criteria, the compound would be ______________.

What is the major organic product obtained from the following reaction?

Provide a brief explanation of why the cyclopentadienyl anion (below) is aromatic. Your answer should identify the hybridization of each carbon atom and account for which electrons are in the pi system.

Which of the following compounds is aromatic?

Which of the following does not undergo oxidation in the presence of H2CrO4?

What is the IUPAC name of the following compound?

The product of the following reaction would be 1-bromo-1-phenylethane.

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Reactions of Benzene and Its Derivatives

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

Filters

Which of the following does not undergo oxidation in the presence of H₂CrO₄?