Question 1

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

Accepted Answer

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

Question 2

The p orbital of a methyl cation,CH3+,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 3

What product(s)would you expect to obtain from the following SN2 reaction?

Accepted Answer

A)  I 
B)  II 
C)  An equimolar mixture of I and II. 
D)  III 
E)  None of these 
A)  I 
B)  II 
C)  An equimolar mixture of I and II. 
D)  III 
E)  None of these

Question 4

What would you expect to be the chief organic product(s)when 2-bromo-2-methylpentane react(s)with sodium propynide,i.e. ,

Accepted Answer

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

Question 5

Which nucleophilic substitution reaction would be unlikely to occur?

Accepted Answer

A)  HO -  + CH3CH2-I $\rightarrow$ CH3CH2-OH + I - 
B)  I -  + CH3CH2-H $\rightarrow$ CH3CH2-I + H - 
C)  CH3S -  + CH3-Br $\rightarrow$CH3S-CH3 + Br - 
D)  All of the above would be unlikely to occur. 
E)  None of the above would be unlikely to occur. 
A)  HO -  + CH3CH2-I $\rightarrow$ CH3CH2-OH + I - 
B)  I -  + CH3CH2-H $\rightarrow$ CH3CH2-I + H - 
C)  CH3S -  + CH3-Br $\rightarrow$CH3S-CH3 + Br - 
D)  All of the above would be unlikely to occur. 
E)  None of the above would be unlikely to occur.

Question 6

Elimination reactions are favored over nucleophilic substitution reactions:

Accepted Answer

A)  at high temperatures. 
B)  when tert-butoxide ion is used. 
C)  when 3 $\degree$ alkyl halides are used as substrates. 
D)  when nucleophiles are used which are strong bases and the substrate is a 2 $\degree$alkyl halide. 
E)  in all of these cases. 
A)  at high temperatures. 
B)  when tert-butoxide ion is used. 
C)  when 3 $\degree$ alkyl halides are used as substrates. 
D)  when nucleophiles are used which are strong bases and the substrate is a 2 $\degree$alkyl halide. 
E)  in all of these cases.

Question 7

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

Question 8

Which would be formed in the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above

Question 9

Considering the relative solvation of reactants and the transition states of substitution reactions of these reactants,predict which general type of reaction would be most favored by the use of a polar solvent.

Accepted Answer

A)  Y: + RX $\rightarrow$ RY+ + X:- 
B)  Y:- + RX $\rightarrow$ RY + X:- 
C)  Y: + RX+ $\rightarrow$RY+ + X: 
D)  Y:- + RX+ $\rightarrow$ RY + X: 
E)  RX+ $\rightarrow$R+ + X: 
A)  Y: + RX $\rightarrow$ RY+ + X:- 
B)  Y:- + RX $\rightarrow$ RY + X:- 
C)  Y: + RX+ $\rightarrow$RY+ + X: 
D)  Y:- + RX+ $\rightarrow$ RY + X: 
E)  RX+ $\rightarrow$R+ + X:

Question 10

In the SN2 reaction,the unstable arrangement of atoms in which both the nucleophile and the leaving group are partially bonded to the same carbon atom is called the ______________________.

Accepted Answer

Question 11

Which alkyl halide would you expect to react most slowly when heated in aqueous solution?

Accepted Answer

A)  (CH3)3C-F 
B)  (CH3)3C-Cl 
C)  (CH3)3C-Br 
D)  (CH3)3C-I 
E)  They would all react at the same rate. 
A)  (CH3)3C-F 
B)  (CH3)3C-Cl 
C)  (CH3)3C-Br 
D)  (CH3)3C-I 
E)  They would all react at the same rate.

Question 12

By analyzing the starting material and the product(s),the following reaction is possibly 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

Question 13

Which is not a polar aprotic solvent?

Accepted Answer

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

Question 14

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

Accepted Answer

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

Question 15

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

Accepted Answer

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

Question 16

For the typical SN2 reaction Y- + RX $\rightarrow$RY + X-
It can be predicted that $\Delta$S‡ will be:

Accepted Answer

A)  positive. 
B)  zero. 
C)  negative. 
D)  either positive or negative. 
E)  unpredictable as to algebraic sign. 
A)  positive. 
B)  zero. 
C)  negative. 
D)  either positive or negative. 
E)  unpredictable as to algebraic sign.

Question 17

Which of the following statements is (are)true of an SN2 reaction of (R)-2-bromobutane with hydroxide ion?

Accepted Answer

A)  Doubling the hydroxide ion concentration would double the rate of the reaction.(Assume that all other experimental conditions are unchanged. ) 
B)  The major product would be (S)-2-butanol. 
C)  Doubling the concentration of (R)-2-bromobutane would double the rate of the reaction.(Assume that all other experimental conditions are unchanged. ) 
D)  All of the above 
E)  Two of the above 
A)  Doubling the hydroxide ion concentration would double the rate of the reaction.(Assume that all other experimental conditions are unchanged. ) 
B)  The major product would be (S)-2-butanol. 
C)  Doubling the concentration of (R)-2-bromobutane would double the rate of the reaction.(Assume that all other experimental conditions are unchanged. ) 
D)  All of the above 
E)  Two of the above

Question 18

Which is the weakest nucleophile in polar protic solvents?

Accepted Answer

A)  I- 
B)  Br- 
C)  Cl- 
D)  F- 
E)  All of the above are equally strong nucleophiles,regardless of the type of solvent used. 
A)  I- 
B)  Br- 
C)  Cl- 
D)  F- 
E)  All of the above are equally strong nucleophiles,regardless of the type of solvent used.

Question 19

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 20

The hybridization state of the charged carbon in a carbocation is

Accepted Answer

A)  sp4 
B)  sp3 
C)  sp2 
D)  sp 
E)  s 
A)  sp4 
B)  sp3 
C)  sp2 
D)  sp 
E)  s

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

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

The p orbital of a methyl cation,CH3+,contains how many electrons?

What product(s)would you expect to obtain from the following SN2 reaction?

What would you expect to be the chief organic product(s)when 2-bromo-2-methylpentane react(s)with sodium propynide,i.e. ,

Which nucleophilic substitution reaction would be unlikely to occur?

Elimination reactions are favored over nucleophilic substitution reactions:

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

Which would be formed in the following reaction?

Considering the relative solvation of reactants and the transition states of substitution reactions of these reactants,predict which general type of reaction would be most favored by the use of a polar solvent.

In the SN2 reaction,the unstable arrangement of atoms in which both the nucleophile and the leaving group are partially bonded to the same carbon atom is called the ______________________.

Which alkyl halide would you expect to react most slowly when heated in aqueous solution?

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

Which is not a polar aprotic solvent?

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

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

For the typical SN2 reaction Y- + RX →\rightarrow→ RY + X- It can be predicted that Δ\DeltaΔ S‡ will be:

Which of the following statements is (are)true of an SN2 reaction of (R)-2-bromobutane with hydroxide ion?

Which is the weakest nucleophile in polar protic solvents?

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

The hybridization state of the charged carbon in a carbocation is

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 a methyl cation,CH₃⁺,contains how many electrons?

What product(s)would you expect to obtain from the following S_N2 reaction?

In the S_N2 reaction,the unstable arrangement of atoms in which both the nucleophile and the leaving group are partially bonded to the same carbon atom is called the ______________________.

For the typical S_N2 reaction Y^- + RX $\rightarrow$ RY + X^- It can be predicted that $\Delta$ S^‡ will be:

Which of the following statements is (are)true of an S_N2 reaction of (R)-2-bromobutane with hydroxide ion?