Question 1

Which is the MAJOR product of combining 1,3-butadiene with HBr at 25 oC?

Accepted Answer

A)  1-bromo-2-butene 
B)  3-bromo-1-butene 
C)  1,3-dibromobutadiene 
D)  2,3-dibromobutene 
E)  3,3-dibromobutene 
A)  1-bromo-2-butene 
B)  3-bromo-1-butene 
C)  1,3-dibromobutadiene 
D)  2,3-dibromobutene 
E)  3,3-dibromobutene B

Question 2

The UV spectrum of the following molecule is useful for determining _______.

Accepted Answer

A)  coupling constants between hydrogen atoms 
B)  molecular weight 
C)  conjugation resulting in electronic transitions 
D)  molecular formula 
E)  two of these are correct 
A)  coupling constants between hydrogen atoms 
B)  molecular weight 
C)  conjugation resulting in electronic transitions 
D)  molecular formula 
E)  two of these are correct C

Question 3

Which of the structures below do not benefit from resonance stabilization?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above. D

Question 4

What would be the expected major product of the following reaction?

Accepted Answer

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

Question 5

The reaction shown below is expected to produce which product(s)?

Accepted Answer

A) 
    
B) 
  
C) 
  
D) 
  
E)  more than one of these 
A) 
    
B) 
  
C) 
  
D) 
  
E)  more than one of these

Question 6

The LUMO of 1,3,5-hexatriene is:

Accepted Answer

A) ( F1F1F1S1F1F1F1010 
B)  (F1F1F1S1F1F1F102) 
C)  (F1F1F1S1F1F1F103) 
D)  (F1F1F1S1F1F1F104) 
E)  (F1F1F1S1F1F1F105) 
A) ( F1F1F1S1F1F1F1010 
B)  (F1F1F1S1F1F1F102) 
C)  (F1F1F1S1F1F1F103) 
D)  (F1F1F1S1F1F1F104) 
E)  (F1F1F1S1F1F1F105)

Question 7

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

Accepted Answer

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

Question 8

The pi electrons in 1,3-butadiene are distributed as follows:

Accepted Answer

A)  One in each of 4 bonding orbitals 
B)  Two in bonding orbitals,two in non-bonding orbitals 
C)  Two in each of 2 bonding orbitals 
D)  One in each of 4 non-bonding orbitals 
E)  None of these. 
A)  One in each of 4 bonding orbitals 
B)  Two in bonding orbitals,two in non-bonding orbitals 
C)  Two in each of 2 bonding orbitals 
D)  One in each of 4 non-bonding orbitals 
E)  None of these.

Question 9

Which of the following are most favored thermodynamically?

Accepted Answer

A) 
  
B) 
  
C) 
  
D)  All of these. 
E)  None of these. 
A) 
  
B) 
  
C) 
  
D)  All of these. 
E)  None of these.

Question 10

Predict the product of the following reaction:

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  No reaction 
A) 
  
B) 
  
C) 
  
D) 
  
E)  No reaction

Question 11

What would be the product of the following reaction?

Accepted Answer

A) 
    
B) 
  
C) 
  
D) 
  
E)  No reaction occurs 
A) 
    
B) 
  
C) 
  
D) 
  
E)  No reaction occurs

Question 12

In order of decreasing reactivity,how would the bromides below rank in the following reaction?

Accepted Answer

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

Question 13

Predict the product of the hydrolysis of (S)-4-bromo-2-pentene.

Accepted Answer

A)  (R)-2-pentene-4-ol 
B)  Racemic 3-pentene-2-ol 
C)  (R)-2-hydroxy-3-pentene 
D)  Racemic-3-hydroxy-3-pentene 
E)  (S)-2-hydroxy-3-pentene 
A)  (R)-2-pentene-4-ol 
B)  Racemic 3-pentene-2-ol 
C)  (R)-2-hydroxy-3-pentene 
D)  Racemic-3-hydroxy-3-pentene 
E)  (S)-2-hydroxy-3-pentene

Question 14

Which of the following alkylbromides cannot be a product of the allylic bromination of 1-methylcyclopentene with NBS?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  All of the above can be a product from the reaction. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  All of the above can be a product from the reaction.

Question 15

What major product would result from the following sequence of reactions?

Accepted Answer

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

Question 16

A typical Diels-Alder reaction involves

Accepted Answer

A)  an electron-rich diene and an electron-rich dienophile. 
B)  an electron-poor diene and an electron-rich dienophile. 
C)  an electron-rich diene and an electron-poor dienophile. 
D)  an electron-poor diene and an electron-poor dienophile. 
E)  a non-substituted diene and a non-substituted dienophile. 
A)  an electron-rich diene and an electron-rich dienophile. 
B)  an electron-poor diene and an electron-rich dienophile. 
C)  an electron-rich diene and an electron-poor dienophile. 
D)  an electron-poor diene and an electron-poor dienophile. 
E)  a non-substituted diene and a non-substituted dienophile.

Question 17

What product(s)would NOT be formed from the reaction of 1,3-butadiene with HCl?

Accepted Answer

A) 
  
B) 
  
C) 
  
D)  neither A nor C 
E)  neither B nor C 
A) 
  
B) 
  
C) 
  
D)  neither A nor C 
E)  neither B nor C

Question 18

Predict the MAJOR product of the following reaction:

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  No reaction 
A) 
  
B) 
  
C) 
  
D) 
  
E)  No reaction

Question 19

What would be the major product of the following reaction?

Accepted Answer

A) 
    
B) 
  
C) 
  
D) 
  
E)  None of these products are formed. 
A) 
    
B) 
  
C) 
  
D) 
  
E)  None of these products are formed.

Question 20

What is the proper IUPAC name for the following molecule:

Accepted Answer

A)  (2E,4Z)-2,4-heptadiene 
B)  (2E,3Z)-2,3-heptadiene 
C)  (2Z,4
E) -2,4-heptadiene 
D)  (2E,4Z)-2,4-hexadiene 
E)  (2Z,3
E) -2,3-hexadiene 
A)  (2E,4Z)-2,4-heptadiene 
B)  (2E,3Z)-2,3-heptadiene 
C)  (2Z,4
E) -2,4-heptadiene 
D)  (2E,4Z)-2,4-hexadiene 
E)  (2Z,3
E) -2,3-hexadiene

Exam 14: Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy Interlude

Which is the MAJOR product of combining 1,3-butadiene with HBr at 25 oC?

The UV spectrum of the following molecule is useful for determining _______.

Which of the structures below do not benefit from resonance stabilization?

What would be the expected major product of the following reaction?

The reaction shown below is expected to produce which product(s)?

The LUMO of 1,3,5-hexatriene is:

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

The pi electrons in 1,3-butadiene are distributed as follows:

Which of the following are most favored thermodynamically?

Predict the product of the following reaction:

What would be the product of the following reaction?

In order of decreasing reactivity,how would the bromides below rank in the following reaction?

Predict the product of the hydrolysis of (S)-4-bromo-2-pentene.

Which of the following alkylbromides cannot be a product of the allylic bromination of 1-methylcyclopentene with NBS?

What major product would result from the following sequence of reactions?

A typical Diels-Alder reaction involves

What product(s)would NOT be formed from the reaction of 1,3-butadiene with HCl?

Predict the MAJOR product of the following reaction:

What would be the major product of the following reaction?

What is the proper IUPAC name for the following molecule:

Structure and Bonding in Organic Molecules

Structure and Reactivity: Acids and Bases,polar and Nonpolar Molecules

Reactions of Alkanes: Bond-Dissociation Energies,radical Halogenation,and Relative Reactivity

Cycloalkanes

Stereoisomers

Properties and Reactions of Haloalkanes: Bimolecular Nucleophilic Substitution

Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

Hydroxy of Functional Group: Alcohols: Properties,preparation,and Strategy of Synthesis

Further Reactions of Alcohols and the Chemistry of Ethers

Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure

Alkenes: Infrared Spectroscopy and Mass Spectrometry

Reactions to Alkenes

Alkynes: the Carbon

Benzene and Aromaticity: Electrophilic Aromatic Substitution

Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity

Aldehydes and Ketones: the Carbonyl Group

Enols,enolates,and the Aldol Condensation: A,b-Unsaturated Aldehydes and Ketones

Carboxylic Acids

Carboxylic Acid Derivatives

Amines and Their Derivatives: Functional Groups Containing Nitrogen

Chemistry of the Benzene Substituents: Alkylbenzenes,phenols,and Benzenamines

Ester Enolates and the Claisen Condensation: Synthesis of B-Dicarbonyl Compounds; Acyl Anion Equivalents

Carbohydrates: Polyfunctional Compounds in Nature

Heterocycles: Heteroatoms in Cyclic Organic Compounds

Amino Acids,peptides,proteins,and Nucleic Acids: Nitrogen-Containing Polymers in Nature

Filters

Which is the MAJOR product of combining 1,3-butadiene with HBr at 25 ^oC?