Question 1

Select the potential energy diagram that represents a two-step endothermic (endergonic)reaction.

Accepted Answer

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

Question 2

Which of the following is not a good leaving group?

Accepted Answer

A)  C2H5O - 
B)  Cl - 
C)  I - 
D)  CH3CO2 - 
E)  All of these are good leaving groups. 
A)  C2H5O - 
B)  Cl - 
C)  I - 
D)  CH3CO2 - 
E)  All of these are good leaving groups. A

Question 3

An increase in the temperature at which a reaction is carried out increases:

Accepted Answer

A)  the collision frequency. 
B)  the fraction of molecules with proper orientation. 
C)  the fraction of molecules with energy greater than Eact. 
D)  More than one of the above 
E)  None of the above 
A)  the collision frequency. 
B)  the fraction of molecules with proper orientation. 
C)  the fraction of molecules with energy greater than Eact. 
D)  More than one of the above 
E)  None of the above D

Question 4

Consider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with methanol.Which of the following would be true?

Accepted Answer

A)  The reaction would take place only with inversion of configuration at the stereogenic center. 
B)  The reaction would take place only with retention of configuration at the stereogenic center. 
C)  The reaction would take place with racemization. 
D)  No reaction would take place. 
E)  The alkyl halide does not possess a stereogenic center. 
A)  The reaction would take place only with inversion of configuration at the stereogenic center. 
B)  The reaction would take place only with retention of configuration at the stereogenic center. 
C)  The reaction would take place with racemization. 
D)  No reaction would take place. 
E)  The alkyl halide does not possess a stereogenic center.

Question 5

A true statement about the transition state(s)of an SN2 reaction is:

Accepted Answer

A)  the two transition states are of unequal energy. 
B)  the transition states precede and follow an unstable reaction intermediate. 
C)  the single transition state represents the point of maximum free energy of the reaction. 
D)  existence of this transition state implies an exothermic reaction. 
E)  the transition state will always have a net charge of -1. 
A)  the two transition states are of unequal energy. 
B)  the transition states precede and follow an unstable reaction intermediate. 
C)  the single transition state represents the point of maximum free energy of the reaction. 
D)  existence of this transition state implies an exothermic reaction. 
E)  the transition state will always have a net charge of -1.

Question 6

Which alkyl halide would be most reactive in an SN1 reaction?

Accepted Answer

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

Question 7

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 8

The major product(s)of the following reaction is(are):

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  Equal amounts of I and II 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  Equal amounts of I and II

Question 9

Identify the leaving group in the following reaction.

Accepted Answer

A)  C6H5S- 
B)  Na+ 
C)  CH3CH2I 
D)  C6H5SCH2CH3 
E)  I- 
A)  C6H5S- 
B)  Na+ 
C)  CH3CH2I 
D)  C6H5SCH2CH3 
E)  I-

Question 10

The major 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 11

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 12

Treating (CH3)3C-Cl with a mixture of H2O and CH3OH at room temperature would yield:

Accepted Answer

A)  CH2=C(CH3)2 
B)  (CH3)3COH 
C)  (CH3)3COCH3 
D)  All of these 
E)  None of these 
A)  CH2=C(CH3)2 
B)  (CH3)3COH 
C)  (CH3)3COCH3 
D)  All of these 
E)  None of these

Question 13

Consider the SN2 reaction of butyl bromide with OH- ion. CH3CH2CH2CH2Br + OH- $\rightarrow$CH3CH2CH2CH2OH + Br-
Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both butyl bromide and OH- 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 14

The major product of the following reaction would be:

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  An equimolar mixture of I and II. 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  An equimolar mixture of I and II.

Question 15

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

Accepted Answer

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

Question 16

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 17

If 0.10 mol of HSCH2CH2OH reacts at 25 $\degree$C,sequentially,with 0.20 mol of NaH,0.10 mol of CH3CH2Br and H2O,which is the major product?

Accepted Answer

A)  HSCH2CH2OCH2CH3 
B)  CH3CH2SCH2CH2OH 
C)  CH3CH2SCH2CH2OCH2CH3 
D)  CH2=CH2 
E)  CH3CH3 
A)  HSCH2CH2OCH2CH3 
B)  CH3CH2SCH2CH2OH 
C)  CH3CH2SCH2CH2OCH2CH3 
D)  CH2=CH2 
E)  CH3CH3

Question 18

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

Accepted Answer

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

Question 19

Which alkyl halide would you expect to undergo an SN2 reaction most slowly?

Accepted Answer

A)  1-bromohexane 
B)  1-bromo-2-methylpentane 
C)  1-bromo-3-methylpentane 
D)  1-bromo-4-methylpentane 
E)  1-bromo-2,2-dimethylbutane 
A)  1-bromohexane 
B)  1-bromo-2-methylpentane 
C)  1-bromo-3-methylpentane 
D)  1-bromo-4-methylpentane 
E)  1-bromo-2,2-dimethylbutane

Question 20

What would be the major product of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  An equimolar mixture of I and II 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  An equimolar mixture of I and II

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

Select the potential energy diagram that represents a two-step endothermic (endergonic)reaction.

Which of the following is not a good leaving group?

An increase in the temperature at which a reaction is carried out increases:

Consider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with methanol.Which of the following would be true?

A true statement about the transition state(s)of an SN2 reaction is:

Which alkyl halide would be most reactive in an SN1 reaction?

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

The major product(s)of the following reaction is(are):

Identify the leaving group in the following reaction.

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

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

Treating (CH3)3C-Cl with a mixture of H2O and CH3OH at room temperature would yield:

Consider the SN2 reaction of butyl bromide with OH- ion. CH3CH2CH2CH2Br + OH- →\rightarrow→ CH3CH2CH2CH2OH + Br- Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both butyl bromide and OH- ion?

The major product of the following reaction would be:

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

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

If 0.10 mol of HSCH2CH2OH reacts at 25 °\degree° C,sequentially,with 0.20 mol of NaH,0.10 mol of CH3CH2Br and H2O,which is the major product?

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

Which alkyl halide would you expect to undergo an SN2 reaction most slowly?

What would be the major product of the following reaction?

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

A true statement about the transition state(s)of an S_N2 reaction is:

Which alkyl halide would be most reactive in an S_N1 reaction?

Treating (CH₃)₃C-Cl with a mixture of H₂O and CH₃OH at room temperature would yield:

Consider the S_N2 reaction of butyl bromide with OH^- ion. CH₃CH₂CH₂CH₂Br + OH^- $\rightarrow$ CH₃CH₂CH₂CH₂OH + Br^- Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both butyl bromide and OH^- ion?

If 0.10 mol of HSCH₂CH₂OH reacts at 25 $\degree$ C,sequentially,with 0.20 mol of NaH,0.10 mol of CH₃CH₂Br and H₂O,which is the major product?

Which alkyl halide would you expect to undergo an S_N2 reaction most slowly?