Question 1

Which of these conjugated dienes can undergo a Diels-Alder reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) All of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) All of these choices.

Question 2

Stereochemically speaking,the Diels-Alder reaction is ___ and occurs with ___ of the dienophile stereochemistry.

Accepted Answer

stereospec

Question 3

From the standpoint of reactivity,which is the poorest choice of dienophile to react with 2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction?

Accepted Answer

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

Question 4

1,3-Pentadiene has how many antibonding $\pi$ molecular orbitals?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) 0 
A) 1 
B) 2 
C) 3 
D) 4 
E) 0

Question 5

Conjugated dienes routinely undergo 1,2 and 1,4 addition reactions with a variety of electrophilic reagents; this suggests that ___ are likely intermediates during these reactions.

Accepted Answer

allylic ca

Question 6

Arrange these hexadienes in order of expected decreasing stability.

Accepted Answer

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

Question 7

Select the structure of the conjugated diene.

Accepted Answer

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

Question 8

What is an IUPAC name for

Accepted Answer

A) 2,3-methylhept-2-en-4-yne 
B) 1,1,3-trimethylhex-3-yn-1-ene 
C) 1,1,3-trimethyl-3-hexyn-1-ene 
D) 2,3-dimethyl-2-hepten-4-yne 
E) 5,6-dimethyl-5-hepten-3-yne 
A) 2,3-methylhept-2-en-4-yne 
B) 1,1,3-trimethylhex-3-yn-1-ene 
C) 1,1,3-trimethyl-3-hexyn-1-ene 
D) 2,3-dimethyl-2-hepten-4-yne 
E) 5,6-dimethyl-5-hepten-3-yne

Question 9

Which carbon-carbon bond in the following compound would you expect to be shortest?

Accepted Answer

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

Question 10

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 further 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 further apart than in a non-cyclic conjugated system.

Question 11

Select the structure(s)in which the multiple bonds are conjugated.

Accepted Answer

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

Question 12

Which of the following can undergo the Diels Alder reaction?

Accepted Answer

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

Question 13

does not undergo the Diels-Alder reaction because:

Accepted Answer

A) ring systems 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) ring systems 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 14

Which is the major product of the following reaction?

Accepted Answer

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

Question 15

The allyl radical 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 16

Which is the major product of the following reaction?

Accepted Answer

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

Question 17

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 18

Which of the following dienes would you expect to be the most stable?

Accepted Answer

A) CH3CH2CH=CHCH2CH=CHCH3 
B) CH3CH=CHCH=CHCH2CH3 
C) CH2=CHCH2CH2CH2CH=CH2 
D) CH2=CHCH=CHCH2CH2CH3 
E) CH3CH=C(CH3)CH=CHCH2CH3 
A) CH3CH2CH=CHCH2CH=CHCH3 
B) CH3CH=CHCH=CHCH2CH3 
C) CH2=CHCH2CH2CH2CH=CH2 
D) CH2=CHCH=CHCH2CH2CH3 
E) CH3CH=C(CH3)CH=CHCH2CH3

Question 19

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 20

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.

Exam 13: Conjugated Unsaturated Systems

Which of these conjugated dienes can undergo a Diels-Alder reaction?

Stereochemically speaking,the Diels-Alder reaction is ___ and occurs with ___ of the dienophile stereochemistry.

From the standpoint of reactivity,which is the poorest choice of dienophile to react with 2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction?

1,3-Pentadiene has how many antibonding π\piπ molecular orbitals?

Conjugated dienes routinely undergo 1,2 and 1,4 addition reactions with a variety of electrophilic reagents; this suggests that ___ are likely intermediates during these reactions.

Arrange these hexadienes in order of expected decreasing stability.

Select the structure of the conjugated diene.

What is an IUPAC name for

Which carbon-carbon bond in the following compound would you expect to be shortest?

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

Select the structure(s)in which the multiple bonds are conjugated.

Which of the following can undergo the Diels Alder reaction?

does not undergo the Diels-Alder reaction because:

Which is the major product of the following reaction?

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

Which is the major product of the following reaction?

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

Which of the following dienes would you expect to be the most stable?

Which reaction would produce the following compound?

Which reaction would produce the following compound?

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

Stereochemically speaking,the Diels-Alder reaction is _ and occurs with _ of the dienophile stereochemistry.

1,3-Pentadiene has how many antibonding $\pi$ molecular orbitals?

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