Question 1

The p orbital of the charged carbon in the isopropyl cation, (CH3)2CH+,contains how many electrons?

Accepted Answer

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

Question 2

What final product is likely to be obtained through the following series of reactions?

Accepted Answer

The answer of What final product is likely to be...

Question 3

The product(s)for the following reaction would mainly be dictated by which mechanism?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  None of the above 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  None of the above

Question 4

What final product is likely to be obtained through the following series of reactions?

Accepted Answer

The answer of What final product is likely to be...

Question 5

Consider the SN2 reaction of 1-chloro-5-methylhexane with CN-ion.   Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both 1-chloro-5-methylhexane and CN- ion?

Accepted Answer

A)  No effect. 
B)  It would double the rate. 
C)  It would triple the rate. 
D)  It would increase the rate four times. 
E)  It would increase the rate six times. 
A)  No effect. 
B)  It would double the rate. 
C)  It would triple the rate. 
D)  It would increase the rate four times. 
E)  It would increase the rate six times.

Question 6

The product(s)for the following reaction would mainly be dictated by which mechanism?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  None of the above 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  None of the above

Question 7

What would be the major product(s)of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  More than one of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  More than one of the above

Question 8

Consider the SN2 reaction of 2-iodopentane with CH3CO2- ion.   Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both 2-iodopentane and CH3CO2- ion?

Accepted Answer

A)  No effect. 
B)  It would double the rate. 
C)  It would triple the rate. 
D)  It would increase the rate four times. 
E)  It would increase the rate six times. 
A)  No effect. 
B)  It would double the rate. 
C)  It would triple the rate. 
D)  It would increase the rate four times. 
E)  It would increase the rate six times.

Question 9

Increasing the temperature of a chemical reaction usually increases greatly the rate of the reaction.The most important reason for this is that increasing the temperature:

Accepted Answer

A)  Increases the collision frequency. 
B)  Decreases the probability factor. 
C)  Increases the fraction of collisions with energy greater than Eact. 
D)  Decreases the energy of activation. 
E)  Makes the reaction more exothermic. 
A)  Increases the collision frequency. 
B)  Decreases the probability factor. 
C)  Increases the fraction of collisions with energy greater than Eact. 
D)  Decreases the energy of activation. 
E)  Makes the reaction more exothermic.

Question 10

Which of the following is a feasible substitution reaction?

Accepted Answer

A)  CH3CH2Cl + NaBr $\rightarrow$CH3CH2Br + NaCl 
B)  CH3CH3 + NaCN $\rightarrow$CH3CH2CN + NaH 
C)  CH3CH2Cl + NaOH $\rightarrow$CH2=CH2 + H2O + NaCl 
D)  More than one of the above. 
E)  None of the above. 
A)  CH3CH2Cl + NaBr $\rightarrow$CH3CH2Br + NaCl 
B)  CH3CH3 + NaCN $\rightarrow$CH3CH2CN + NaH 
C)  CH3CH2Cl + NaOH $\rightarrow$CH2=CH2 + H2O + NaCl 
D)  More than one of the above. 
E)  None of the above.

Question 11

The product(s)for the following reaction would mainly be dictated by which mechanism?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  None of the above 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  None of the above

Question 12

Treating 1-bromo-1-methylcyclohexane with CH3OH at room temperature would yield:

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 13

Increasing the temperature of a chemical reaction usually increases greatly the rate of the reaction.The primary reason for this is that increasing the temperature:

Accepted Answer

A)  Decreases the energy of activation. 
B)  Increases the total number of collisions between reactants. 
C)  Decreases the rate of the reverse reaction. 
D)  Favors endothermic processes. 
E)  None of the above properly explains the observed increase in reaction rates with increase in temperature. 
A)  Decreases the energy of activation. 
B)  Increases the total number of collisions between reactants. 
C)  Decreases the rate of the reverse reaction. 
D)  Favors endothermic processes. 
E)  None of the above properly explains the observed increase in reaction rates with increase in temperature.

Question 14

Which of the following is the poorest leaving group?

Accepted Answer

A)  H - 
B)  CH3O - 
C)  H2O 
D)  OH - 
E)  NH2 - 
A)  H - 
B)  CH3O - 
C)  H2O 
D)  OH - 
E)  NH2 -

Question 15

Which nucleophilic substitution reaction is not likely to occur?

Accepted Answer

A)  I -  + CH3CH2-Cl $\rightarrow$CH3CH2-I + Cl - 
B)  I -  + CH3CH2-Br $\rightarrow$ CH3CH2-I + Br - 
C)  I -  + CH3CH2-OH $\rightarrow$ CH3CH2-I + OH - 
D)  CH3O -  + CH3CH2-Br $\rightarrow$CH3CH2-OCH3 + Br - 
E)  OH -  + CH3CH2-Cl $\rightarrow$CH3CH2-OH + Cl - 
A)  I -  + CH3CH2-Cl $\rightarrow$CH3CH2-I + Cl - 
B)  I -  + CH3CH2-Br $\rightarrow$ CH3CH2-I + Br - 
C)  I -  + CH3CH2-OH $\rightarrow$ CH3CH2-I + OH - 
D)  CH3O -  + CH3CH2-Br $\rightarrow$CH3CH2-OCH3 + Br - 
E)  OH -  + CH3CH2-Cl $\rightarrow$CH3CH2-OH + Cl -

Question 16

SN1 reactions of the type,Nu- + RL $\rightarrow$ Nu-R + L-,are favored:

Accepted Answer

A)  when tertiary substrates are used. 
B)  by using a high concentration of the nucleophile. 
C)  when L- is a strong base. 
D)  by use of a non-polar solvent. 
E)  by none of the above. 
A)  when tertiary substrates are used. 
B)  by using a high concentration of the nucleophile. 
C)  when L- is a strong base. 
D)  by use of a non-polar solvent. 
E)  by none of the above.

Question 17

What would be the major product(s)of the following reaction?

Accepted Answer

A)  I and II 
B)  II and III 
C)  I and III 
D)  IV 
E)  None of the above 
A)  I and II 
B)  II and III 
C)  I and III 
D)  IV 
E)  None of the above

Question 18

What would be the major product(s)of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  More than one of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  More than one of the above

Question 19

Consider the substitution reaction that takes place when (R)-3-iodo-3-methylheptane is treated with sodium acetate (CH3CO2Na).Which of the following would be true?

Accepted Answer

A)  An SN2 reaction would take place with inversion of configuration at the stereogenic center. 
B)  An SN1 reaction would take place with retention of configuration at the stereogenic center. 
C)  An SN1 reaction would take place with racemization of configuration at the stereogenic center. 
D)  An SN1 reaction would take place,accompanied by an E1 reaction,affording a complex mixture of products. 
E)  An E2 reaction would take place,during which the stereogenic center is lost. 
A)  An SN2 reaction would take place with inversion of configuration at the stereogenic center. 
B)  An SN1 reaction would take place with retention of configuration at the stereogenic center. 
C)  An SN1 reaction would take place with racemization of configuration at the stereogenic center. 
D)  An SN1 reaction would take place,accompanied by an E1 reaction,affording a complex mixture of products. 
E)  An E2 reaction would take place,during which the stereogenic center is lost.

Question 20

By analyzing the starting material and the product(s),the following reaction is an example of what type of mechanism?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  None of the above 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  None of the above

Exam 6: Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

The p orbital of the charged carbon in the isopropyl cation, (CH3)2CH+,contains how many electrons?

What final product is likely to be obtained through the following series of reactions?

The product(s)for the following reaction would mainly be dictated by which mechanism?

What final product is likely to be obtained through the following series of reactions?

Consider the SN2 reaction of 1-chloro-5-methylhexane with CN-ion. Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both 1-chloro-5-methylhexane and CN- ion?

The product(s)for the following reaction would mainly be dictated by which mechanism?

What would be the major product(s)of the following reaction?

Consider the SN2 reaction of 2-iodopentane with CH3CO2- ion. Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both 2-iodopentane and CH3CO2- ion?

Increasing the temperature of a chemical reaction usually increases greatly the rate of the reaction.The most important reason for this is that increasing the temperature:

Which of the following is a feasible substitution reaction?

The product(s)for the following reaction would mainly be dictated by which mechanism?

Treating 1-bromo-1-methylcyclohexane with CH3OH at room temperature would yield:

Increasing the temperature of a chemical reaction usually increases greatly the rate of the reaction.The primary reason for this is that increasing the temperature:

Which of the following is the poorest leaving group?

Which nucleophilic substitution reaction is not likely to occur?

SN1 reactions of the type,Nu- + RL →\rightarrow→ Nu-R + L-,are favored:

What would be the major product(s)of the following reaction?

What would be the major product(s)of the following reaction?

Consider the substitution reaction that takes place when (R)-3-iodo-3-methylheptane is treated with sodium acetate (CH3CO2Na).Which of the following would be true?

By analyzing the starting material and the product(s),the following reaction is an example of what type of mechanism?

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

The p orbital of the charged carbon in the isopropyl cation, (CH₃)₂CH⁺,contains how many electrons?

Consider the S_N2 reaction of 1-chloro-5-methylhexane with CN-ion. Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both 1-chloro-5-methylhexane and CN- ion?

Consider the S_N2 reaction of 2-iodopentane with CH₃CO₂- ion. Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both 2-iodopentane and CH₃CO₂- ion?

Treating 1-bromo-1-methylcyclohexane with CH₃OH at room temperature would yield:

S_N1 reactions of the type,Nu^- + RL $\rightarrow$ Nu-R + L^-,are favored:

Consider the substitution reaction that takes place when (R)-3-iodo-3-methylheptane is treated with sodium acetate (CH₃CO₂Na).Which of the following would be true?