Question 1

Which of the indicated C-C bonds requires the least amount of energy to break homolytically?

Accepted Answer

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

Question 2

Which of the following monobrominated products forms fastest under the conditions shown?

Accepted Answer

A)    
B)    
C)    
D)    
E)  All form at equal rates. 
A)    
B)    
C)    
D)    
E)  All form at equal rates. B

Question 3

Which of the following compounds is the product of this reaction?

Accepted Answer

A)    
B)    
C)    
D)    
E)  Both  a  and  b  would be produced. 
A)    
B)    
C)    
D)    
E)  Both  a  and  b  would be produced. E

Question 4

Draw all the constitutional isomers of the monochloroalkane generated from the free radical
chlorination of methylcyclohexane.Which of the constitutional isomers would also have
stereoisomers?

Accepted Answer

The answer of Draw all the constitutional isomers of the...

Question 5

Which of the following monomers will react to provide the polymer shown here?

Accepted Answer

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

Question 6

What is the principal monobrominated product that would result from the conditions shown?

Accepted Answer

The answer of What is the principal monobrominated product that...

Question 7

Devise a multistep synthesis of the target molecule from the given starting material.Show the
reagents needed for each step and the product of each step.

Accepted Answer

The answer of Devise a multistep synthesis of the target...

Question 8

Which is the following would not be a valid resonance form for this radical?

Accepted Answer

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

Question 9

A chemist would like to prepare a tertiary alcohol via the following reaction sequence.
 
What halogen  X  should be used to ensure the maximum selectivity for the intermediate haloalkane?

Accepted Answer

Bromine would selectively halo

Question 10

Anti-Markovnikov addition of HX to an alkene only works with HBr in the presence of peroxides
as a radical initiator.Use the bond dissociation data provided to explain why the reaction fails
with HCl and HI.

Accepted Answer

For HI, the reaction fails because the f

Question 11

What is the name of the process shown here?

Accepted Answer

A)  disproportionation 
B)  hydrogen abstraction 
C)   β cleavage 
D)  dimerization 
E)  pyrolysis 
A)  disproportionation 
B)  hydrogen abstraction 
C)   β cleavage 
D)  dimerization 
E)  pyrolysis

Question 12

Which of the following transformations is a disproportionation?

Accepted Answer

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

Question 13

Draw an arrow-pushing mechanism for the transformation shown here.

Accepted Answer

The answer of Draw an arrow-pushing mechanism for the transformation...

Question 14

Draw an arrow-pushing mechanism to show the transformation of dibromomethane to bromoform in
the presence of molecular bromine and bromine radical.

Accepted Answer

The answer of Draw an arrow-pushing mechanism to show the...

Question 15

Devise a multistep synthesis of the target molecule from the given starting material.Show the
reagents needed for each step and the product of each step.Explain why the target cannot be made
from the starting material in one step.

Accepted Answer

The anti-Markovnikov addition of HI to a

Question 16

Draw the products of the following reaction.

Accepted Answer

The answer of Draw the products of the following reaction....

Question 17

In an allylic bromination, why is it essential to keep the concentration of molecular bromine relatively low?

Accepted Answer

Alkenes react with Br₂ to pro

Question 18

Using the bond dissociation energies provided below, draw an energy diagram for the two
propagation steps in the following reaction.  
Show the correct relative energies of intermediates, starting materials and products. Estimate the  
Bond dissociation energies (kcal/mol)

Accepted Answer

The answer of Using the bond dissociation energies provided below,...

Question 19

Provide the structures of all monochlorinated products that would result from the conditions
shown.Assume that all chiral products are formed as racemic mixtures.

Accepted Answer

The answer of Provide the structures of all monochlorinated products...

Question 20

The disproportionation product(s) of the alkyl radical shown here will be

Accepted Answer

A)  two alkanes. 
B)  an alkane and an alkene. 
C)  one alkane. 
D)  one alkene. 
E)  two alkenes. 
A)  two alkanes. 
B)  an alkane and an alkene. 
C)  one alkane. 
D)  one alkene. 
E)  two alkenes.

Exam 12: Radical Reactions

Which of the indicated C-C bonds requires the least amount of energy to break homolytically?

Which of the following monobrominated products forms fastest under the conditions shown?

Which of the following compounds is the product of this reaction?

Draw all the constitutional isomers of the monochloroalkane generated from the free radical chlorination of methylcyclohexane.Which of the constitutional isomers would also have stereoisomers?

Which of the following monomers will react to provide the polymer shown here?

What is the principal monobrominated product that would result from the conditions shown?

Devise a multistep synthesis of the target molecule from the given starting material.Show the reagents needed for each step and the product of each step.

Which is the following would not be a valid resonance form for this radical?

A chemist would like to prepare a tertiary alcohol via the following reaction sequence. What halogen X should be used to ensure the maximum selectivity for the intermediate haloalkane?

Anti-Markovnikov addition of HX to an alkene only works with HBr in the presence of peroxides as a radical initiator.Use the bond dissociation data provided to explain why the reaction fails with HCl and HI.

What is the name of the process shown here?

Which of the following transformations is a disproportionation?

Draw an arrow-pushing mechanism for the transformation shown here.

Draw an arrow-pushing mechanism to show the transformation of dibromomethane to bromoform in the presence of molecular bromine and bromine radical.

Devise a multistep synthesis of the target molecule from the given starting material.Show the reagents needed for each step and the product of each step.Explain why the target cannot be made from the starting material in one step.

Draw the products of the following reaction.

In an allylic bromination, why is it essential to keep the concentration of molecular bromine relatively low?

Using the bond dissociation energies provided below, draw an energy diagram for the two propagation steps in the following reaction. Show the correct relative energies of intermediates, starting materials and products. Estimate the Bond dissociation energies (kcal/mol)

Provide the structures of all monochlorinated products that would result from the conditions shown.Assume that all chiral products are formed as racemic mixtures.

The disproportionation product(s) of the alkyl radical shown here will be

Atoms and Molecules; Orbitals and Bonding

Alkanes

Alkenes and Alkynes

Stereochemistry

Rings

Substituted Alkanes: Alkyl Halides, Alcohols, Amines, Ethers,thiols, and Thioethers

Substitution Reactions: the Sn2 and Sn1 Reactions

Elimination Reactions: the E1 and E2 Reactions

Analytical Chemistry: Spectroscopy

Electrophilic Additions to Alkenes

More Additions to Bonds

Dienes and the Allyl System: 2p Orbitals in Conjugation

Aromaticity

Substitution Reactions of Aromatic Compounds

Carbonyl Chemistry 1: Addition Reactions

Carboxylic Acids

Derivatives of Carboxylic Acids: Acyl Compounds

Carbonyl Chemistry 2: Reactions at the Α Position

Special Topic: Carbohydrates

Special Topic: Bio-Organic Chemistry

Special Topic: Amino Acids and Polyamino Acids Peptides and Proteins

Special Topic: Reactions Controlled by Orbital Symmetry

Special Topic: Intramolecular Reactions and Neighboring Group Participation

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