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Homework answers / question archive / Wayne State University CHEM 1240 Chapter 8 1)What is the degree of substitution of the following alkene? Monosubstituted Disubstituted Trisubstituted Tetrasubstituted         What is the degree of substitution of the following alkene? Monosubstituted Disubstituted Trisubstituted Tetrasubstituted         What is the degree of substitution of the following alkene? Monosubstituted Disubstituted Trisubstituted Tetrasubstituted         Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol

Wayne State University CHEM 1240 Chapter 8 1)What is the degree of substitution of the following alkene? Monosubstituted Disubstituted Trisubstituted Tetrasubstituted         What is the degree of substitution of the following alkene? Monosubstituted Disubstituted Trisubstituted Tetrasubstituted         What is the degree of substitution of the following alkene? Monosubstituted Disubstituted Trisubstituted Tetrasubstituted         Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol

Chemistry

Wayne State University

CHEM 1240

Chapter 8

1)What is the degree of substitution of the following alkene?

  1. Monosubstituted
  2. Disubstituted
  3. Trisubstituted
  4. Tetrasubstituted

 

 

  1.  
     

    What is the degree of substitution of the following alkene?
  1. Monosubstituted
  2. Disubstituted
  3. Trisubstituted
  4. Tetrasubstituted

 

 

  1.  
     

    What is the degree of substitution of the following alkene?
  1. Monosubstituted
  2. Disubstituted
  3. Trisubstituted
  4. Tetrasubstituted

 

 

 

 

  1. Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. What is the degree of substitution of the alkene of Crestor®?

  1. Monosubstituted
  2. Disubstituted
  3. Trisubstituted
  4. Tetrasubstituted

 

 

 

  1.  
     

    Drawn below is the structure of Singulair® (montelukast), a medication used to manage athsma. What is the degree of substitution of the alkene of Singulair®?
  1. Monosubstituted
  2. Disubstituted
  3. Trisubstituted
  4. Tetrasubstituted

 

 

 

  1.  
     

    Provide an IUPAC name for the following compound.

Ans: 5-methyl-1-hexene

 

 

 

 

  1.  
     

    Provide an IUPAC name for the following compound.

Ans: 3-ethyl-2,4-dimethyl-2-pentene

 

 

 

  1.  
     

    Provide an IUPAC name for the following compound.

Ans: 3-methylcyclohexene

 

 

 

  1.  
     

    Which of the following is the IUPAC name for the following compound?
  1. 1-methyl-2-cyclohexene
  2. 2-methylcyclohexene
  3. 3-methylcyclohexene
  4. 1-methyl-5-cyclohexene

 

 

 

  1.  
     

    Which of the following is the IUPAC name for the following compound?
  1. 2-ethyl-1,1,3-trimethylbutene
  2. 3-ethyl-2,4-dimethyl-2-pentene
  3. 2,4-dimethylhexene
  4. 4-ethyl-1,3-dimethyl-3-pentene

 

 

 

  1. Which of the following is the correct structure of 4-methylcyclopentene?

 

                                                     

 

               
       
 

 

 

 

 

 

  1.                
           
     
     

    Which of the following is the correct structure of 2-methyl-1-butene?

 

 

 

 

 

  1. Draw the structure of 3-methylcyclopentene.

 

 

 

 

 

  1. Draw the structure of 2,3-dimethyl-1-pentene.

 

 

 

 

  1. Provide an IUPAC name for the following compound.

 

 

 

  1. Is the geometry of the following alkene E, Z, or neither?

 

 

 

 

  1. Is the geometry of the following alkene E, Z, or neither?

 

 

 

  1. Is the geometry of the following alkene E, Z, or neither?

 

 

 

  1. Is the geometry of the following alkene E, Z, or neither?

 

 

 

  1. Draw the E isomer of 2-methyl-3-heptene.

 

 

 

 

  1. Draw the E isomer of 3,4-dimethyl-3-hexene.

 

 

 

 

 

  1. Draw the Z isomer of 3,4-dimethyl-3-hexene.

 

 

 

 

  1. Viridenomycin, shown below, is a polyene antibiotic that displays anti-tumor activity. Its structural complexity and chemical instability have made it a challenging target for organic chemists to synthesize. Ignoring the benzene ring, how many disubstituted Z alkenes are present in viridenomycin?

    1. 1
    2. 2
    3. 3
    4. 4

 

 

 

 

  1. Rank the following from most to least stable.

 

                                                                                           

, B, A, C

 

 

 

  1.            
         
     

    Rank the following from most to least stable.

 

  1. A, B, C

 

  1. C, B, A
  2. B, C, A
  3. B, A, C

 

 

 

  1.        
       
     

    Which of the following alkenes is more stable?

 

 

 

 

 

  1. Given the following alkane, draw the least stable alkene isomer with the same basic skeleton.

 

 

 

 

 

  1.            
         
     

    Rank the following from most to least stable.

 

, C, A

 

 

 

  1. Show the mechanism for the following elimination, assuming that it is a concerted reaction.

 

 

 

 

               
 
     
 
   
 
 

 

 

 

 

 
  1. Show the mechanism for the following elimination, assuming that it is a concerted reaction.

 

 

 

 

 

 

 
  1. Show the mechanism for the following elimination, assuming that it is a concerted reaction.

 

 

 

 

 

 

       
   
 
 

 

 

 

 

 

 

 
  1. Which of the following shows a mechanism of a concerted elimination?

 

                                                     

 

               
       
 
 
 

 

 

 

 

               
   
     
 
 
     
 
 

 

 
  1.            
         
     

    Which of the following is the most reactive in an E2 reaction?

 

 

 

 

 

 

  1. Which of the following is the major product of the following elimination?

 

 

 

 

           
   
     
 
 
 

 

 

 

 
  1. Which of the following is the major product of the following elimination?

 

 

 

 

 

               
 
 
   
     
   
 
 

 

 

 

 

 

 
  1. Draw the major product of the following elimination.

 

 

 

  1.            
         
     
     

    What would be the best base for performing the following elimination?

 

 

 

  1.                
           
     
     
     

    Which of the following would be the best base for performing the following elimination?

 

 

 or A

 

 

 

  1. What is the product of the following elimination?

 

 

 

 

 

 

 

 

 

 

  1. What is the product of the following elimination?

 

 

 

 

 

 

 

  1. What is the product of the following elimination?

 

 

 

 

 

 

 

  1.                
           
     
     
     

    Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide?

 

 

 

 

 

  1.                    
             
     

    Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide?

 

 

 or D

 

 

 

  1.        
       
     

    Which of the following alkyl halides would be more reactive in an E2 elimination?

                                         

 

 

 

 

  1. Draw the isomer of 2-bromo-1,1,3-trimethylcyclohexane that would be more reactive in an E2 elimination.

 

 

 

                                   

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

 

 

 

 

 

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

 

 

 

 

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

 

 

 

 

 

 

 

  1. Draw the major product of the following elimination.

 

 

 

 

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

 

 

 

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

 

 

 

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

 

  1. Draw the major product of the following reaction.

 

 

 

  1.            
         
     

    Which of the following is most reactive in an E1 reaction?

 

 

 

 

 

  1.            
         
     
     

    Which of the following is most reactive in an E1 reaction?

 

 

 

 

 

  1. Based upon the following energy diagram, is this reaction an E1 or an E2 elimination?

 

 

 

  1. Based upon the following energy diagram, is this reaction an E1 or an E2 elimination?

 

 

 

  1. For the following dehydration, draw the structure of the intermediate carbocation.

 

 

 

 

 

  1. For the following dehydration, draw the structure of the intermediate carbocation.

 

 

 

 

 

 

 

  1. For the following dehydration, draw the structure of the intermediate carbocation.

 

 

 

 

 

 

  1. Draw the major organic product of the following dehydration reaction.

 

 

 

 

 

 

  1. Draw the product of the following dehydration reaction.

 

 

 

 

 

 

 

 

 

  1. Draw the product of the following dehydration reaction.

 

 

 

 

 

  1. Draw the mechanism for the following dehydration.

 

 

 

 

 

 

 

 

  1. Draw the mechanism for the following dehydration.

 

 

 

 

 

 

  1. What is the first step of the following dehydration?

 

                                                               

 

                           
           
   
 
 
 
 
 
 
 

 

 

 

 

 
  1. Which of the following is the energy diagram for the following reaction?

 

 

 

 

 

 
 
 

 

 

 

 

 

  1. Draw an energy diagram for the following reaction, assuming that it is exothermic.

 

 

 

 

 

  1. Which pattern of arrow pushing is associated with the first step in any dehydration reaction?

 

 

 

  1. What are the steps of arrow pushing involved in the following mechanism?

 

 
 
 

 

 

 

 

 

  1. Will the following alcohol undergo rearrangement during a dehydration reaction?

 

 

 

  1. Will the following alcohol be likely to undergo rearrangement during a dehydration reaction?

 

 

 

  1.  
     

    What is the structure of a rearranged carbocation that does not have a four- membered ring in the following acid-catalyzed dehydration of the following compound?

 

 

 

 

 

 

  1. What is the structure of the rearranged carbocation intermediate in the following dehydration?

 

 

 

 

 

  1. Which of the following is the structure of the rearranged carbocation intermediate in the following dehydration?

 

 

 

 

 

               
       
 

 

 

 

 

 

  1. Draw the mechanism and product for the following elimination.

 

                                                                                    

 

 
 
 

 

 

 

 

  1. Draw the mechanism and product for the following elimination, without using rearrangement.

 

 

 

 

 

 

 

 

 

 

  1. Draw the mechanism and product for the following elimination.

 

 

 

 

                                                                    

 

 

 

 

  1. Draw the mechanism and product for the following elimination.

 

 

 

  1. Which of the following is the correct mechanism for the elimination reaction of 2- bromo-2,3-dimethylbutane with methoxide?

 

 

 

 

  1. Which of the following is the correct mechanism for the elimination reaction of 1- bromo-2-methylcyclopentane with methoxide?

 

 

 

 

 

 

  1. Draw the mechanism and product for the following elimination.

 

 

 

 

  1. Draw the mechanism and product for the following elimination.

 

 

 

 

  1. Is the following more likely a nucleophile or a base?

 

 

 

 

 

  1. Is the following more likely a nucleophile or a base?

ase

 

 

 

  1.            
         
     

    Which of the following is the strongest nucleophile?

 

                                                                                          

 

 

 

 

  1.                    
             
     
     
     

    Which of the following is the strongest nucleophile?

 

 

 

 

 

  1.                
           
     
     

    Which of the following is most likely to act as a base rather than a nucleophile?

 

 

 

 

 

 

  1.                        
               
     
     
     
     

    Which of the following is most likely to act as a base rather than a nucleophile?

 

 

 

 

 

  1. By what mechanism is the following reaction likely to occur?

 

 

 

 

 

 

 

  1. By what mechanism is the following reaction likely to occur?

 

 

 

 

 

 

 

  1.  
     

    By what mechanism is the following reaction likely to occur?

       

 

 

 

  1. By what mechanism is the following reaction likely to occur?

 

 

 

 

 

 

 

  1. By what mechanism is the following reaction likely to occur?

 

 

 

 

 

 

  1. How would you change the following reaction conditions to favor an E2 mechanism?

 

 

 

 

 

 

  1. How would you change the following reaction conditions to favor an E1 mechanism?

 

 

 

 

 

 

 

  1. What is (are) the most likely product(s) for the following reaction?

 

 

  1. What is (are) the most likely product(s) for the following reaction?

 

 

 

 

 

 

  1. What is (are) the most likely product(s) for the following reaction?

 

 

 

 

 

 

 

 

 

  1. What is (are) the most likely product(s) for the following reaction?

 

 

 

 

 

 

 

 

 

  1. What is (are) the most likely product(s) for the following reaction?

 

 

 

 

 

 

 

 

  1. What is (are) the most likely product(s) for the following reaction?

 

 

 

 

 

 

 

 

 

 

       
   
 
 

 

 
  1. What is (are) the most likely product(s) for the following reaction?

 

 

 

  1. What is (are) the most likely product(s) for the following reaction?

 

 

  1. Viridenomycin, shown below, is a polyene antibiotic that displays anti- tumor activity. Its structural complexity and chemical instability have made it a challenging target for organic chemists to synthesize. Ignoring the benzene ring, circle any trisubstituted alkene(s), and put a box around any Z alkene(s).

 

 

 

 

 

  1. How many distinct signals would appear in the (proton-decoupled) 13C NMR spectrum for the following compound?

 

    1. 4
    2. 5
    3. 6
    4. 8

 

 

  1. How many distinct resonances would appear in the (proton-decoupled) 13C NMR spectrum in the region between 100-130 ppm for the following compound?

 

    1. 3
    2. 4
    3. 5
    4. 6

 

 

  1. A student runs an elimination reaction in lab, beginning with 1-iodo-1- methyl cyclohexane. If the product obtained shows exactly 5 distinct carbons in the (proton-decoupled) 13C NMR spectrum, what base could have been used to cause the elimination?

 

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