Question 1

The allyl cation has how many bonding $\pi$ molecular orbitals?

Accepted Answer

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

Question 2

Which is the major product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III + enantiomer 
D) IV 
E) V 
A) I 
B) II 
C) III + enantiomer 
D) IV 
E) V

Question 3

Which is the major product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III + enantiomer 
D) IV + enantiomer 
E) V 
A) I 
B) II 
C) III + enantiomer 
D) IV + enantiomer 
E) V

Question 4

Which is the only compound which can be completely ruled out as a product of the reaction of 1,3-butadiene with HCl?

Accepted Answer

A) (S)-3-chloro-1-butene 
B) (R)-3-chloro-1-butene 
C) (
E) -1-chloro-2-butene 
D) (Z)-1-chloro-2-butene 
E) (Z)-2-chloro-2-butene 
A) (S)-3-chloro-1-butene 
B) (R)-3-chloro-1-butene 
C) (
E) -1-chloro-2-butene 
D) (Z)-1-chloro-2-butene 
E) (Z)-2-chloro-2-butene

Question 5

Which of the following compounds would be the most stable?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) They are all of equal stability. 
A) I 
B) II 
C) III 
D) IV 
E) They are all of equal stability.

Question 6

Which of the following would afford a synthesis of the following compound?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) None of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) None of these choices.

Question 7

Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) More than one of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) More than one of these choices.

Question 8

Which is not an example of resonance?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) None of these choices are examples of resonance. 
A) I 
B) II 
C) III 
D) IV 
E) None of these choices are examples of resonance.

Question 9

Arrange these carbocations in order of expected increasing stability.

Accepted Answer

A) V < II < I < IV < III 
B) V < I < II < IV < III 
C) IV < I < II < V < III 
D) IV < III < I < II < V 
E) I < II < IV < III < V 
A) V < II < I < IV < III 
B) V < I < II < IV < III 
C) IV < I < II < V < III 
D) IV < III < I < II < V 
E) I < II < IV < III < V

Question 10

Arrange these carbocations in order of expected increasing stability.

Accepted Answer

A) V < II < I < IV < III 
B) V < I < II < IV < III 
C) IV <I < II < V < III 
D) IV < III < I < II < V 
E) II < III < IV < V < I 
A) V < II < I < IV < III 
B) V < I < II < IV < III 
C) IV <I < II < V < III 
D) IV < III < I < II < V 
E) II < III < IV < V < I

Question 11

Which carbocation would be most stable?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 12

When the product distribution for a particular reaction reflects the relative stabilities of the products,the reaction is said to be under ___ control.

Accepted Answer

The answer of When the product distribution for a particular...

Question 13

Which diene would be least reactive toward Diels-Alder addition of maleic anhydride?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 14

Which reaction would produce the following compound?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) None of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) None of these choices.

Question 15

Which compounds could be used in a Diels-Alder synthesis of

Accepted Answer

A) I and III 
B) I and IV 
C) II and III 
D) II and IV 
E) I and II 
A) I and III 
B) I and IV 
C) II and III 
D) II and IV 
E) I and II

Question 16

does not undergo the Diels-Alder reaction as a diene because:

Accepted Answer

A) a bicyclic ring system cannot function as the diene component. 
B) it cannot adopt the s-cis conformation. 
C) it lacks electron-withdrawing groups. 
D) it lacks strong electron-releasing groups. 
E) the two double bonds are farther apart than in a non-cyclic conjugated system. 
A) a bicyclic ring system cannot function as the diene component. 
B) it cannot adopt the s-cis conformation. 
C) it lacks electron-withdrawing groups. 
D) it lacks strong electron-releasing groups. 
E) the two double bonds are farther apart than in a non-cyclic conjugated system.

Question 17

Which carbocation would be least stable?

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 18

Systems that have a p orbital on an atom adjacent to a double bond are called ___ systems.

Accepted Answer

conjugated

Question 19

The first step in the total synthesis of synthetic cholesterol involves production of the intermediate structure shown.Which combination of diene and dieneophile will result in its preparation?

Accepted Answer

The answer of The first step in the total synthesis...

Question 20

Which compound would have a UV absorption band at longest wavelength?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Exam 13: Conjugated Unsaturated Systems

The allyl cation has how many bonding π\piπ molecular orbitals?

Which is the major product of the following reaction?

Which is the major product of the following reaction?

Which is the only compound which can be completely ruled out as a product of the reaction of 1,3-butadiene with HCl?

Which of the following compounds would be the most stable?

Which of the following would afford a synthesis of the following compound?

Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below?

Which is not an example of resonance?

Arrange these carbocations in order of expected increasing stability.

Arrange these carbocations in order of expected increasing stability.

Which carbocation would be most stable?

When the product distribution for a particular reaction reflects the relative stabilities of the products,the reaction is said to be under ___ control.

Which diene would be least reactive toward Diels-Alder addition of maleic anhydride?

Which reaction would produce the following compound?

Which compounds could be used in a Diels-Alder synthesis of

does not undergo the Diels-Alder reaction as a diene because:

Which carbocation would be least stable?

Systems that have a p orbital on an atom adjacent to a double bond are called ___ systems.

The first step in the total synthesis of synthetic cholesterol involves production of the intermediate structure shown.Which combination of diene and dieneophile will result in its preparation?

Which compound would have a UV absorption band at longest wavelength?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

The allyl cation has how many bonding $\pi$ molecular orbitals?