Question 1

Predict the product(s)for the following reaction sequence.

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above 
A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above

Question 2

When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether,the product is analyzed to be C5H10O.Propose a likely structure for this product,suggesting a reasonable mechanistic pathway for its formation.

Accepted Answer

The alcohol is likely to be fi

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

Accepted Answer

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

Question 5

Ambident nucleophiles are ones which can react with a substrate at either of two nucleophilic sites.Which of the following is not an ambident nucleophile?

Accepted Answer

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

Question 6

Which is the most reactive nucleophile in DMF (structure shown below)?

Accepted Answer

A)  F- 
B)  Cl- 
C)  Br- 
D)  I- 
E)  They are all equally reactive. 
A)  F- 
B)  Cl- 
C)  Br- 
D)  I- 
E)  They are all equally reactive.

Question 7

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 8

Select the rate law for the following reaction,e.g. , CH3CH2CH2CHBrCH3 + OH - $\rightarrow$CH3CH2CH2CHOHCH3 + X - 
( RBr )

Accepted Answer

A)  Rate = k [RBr] 
B)  Rate = k [RBr] [OH - ] 
C)  Rate = k [RBr]2 [OH - ] 
D)  Rate = k [RBr] [OH - ]2 
E)  Rate = k [RBr]2 [OH - ]2 
A)  Rate = k [RBr] 
B)  Rate = k [RBr] [OH - ] 
C)  Rate = k [RBr]2 [OH - ] 
D)  Rate = k [RBr] [OH - ]2 
E)  Rate = k [RBr]2 [OH - ]2

Question 9

Heating tert-butyl chloride with 1.0 M NaOH in a mixture of water and methanol would yield mainly:

Accepted Answer

A)  (CH3)3COH through an SN1 reaction. 
B)  (CH3)3COCH3 through an SN1 reaction. 
C)  (CH3)3COH through an SN2 reaction. 
D)  (CH3)3COCH3 through an SN2 reaction. 
E)  CH2=C(CH3)2 through an E2 reaction. 
A)  (CH3)3COH through an SN1 reaction. 
B)  (CH3)3COCH3 through an SN1 reaction. 
C)  (CH3)3COH through an SN2 reaction. 
D)  (CH3)3COCH3 through an SN2 reaction. 
E)  CH2=C(CH3)2 through an E2 reaction.

Question 10

Which nucleophilic substitution reaction would be likely to occur (although probably not in excellent yield,due to competing elimination)?

Accepted Answer

A)  HO -  + CH3CH2CH2CHICH3 $\rightarrow$ CH3 CH2CH2CHOHCH3 + I - 
B)  Cl - + CH3CH2CH2CH2-OH $\rightarrow$CH3CH2CH2CH2-Cl + OH - 
C)  CH3S -  + CH3CH2CH2-OCH3 $\rightarrow$ CH3S-CH2CH2CH3 + OCH3 - 
D)  All of the above are likely to occur 
E)  None of the above are likely to occur 
A)  HO -  + CH3CH2CH2CHICH3 $\rightarrow$ CH3 CH2CH2CHOHCH3 + I - 
B)  Cl - + CH3CH2CH2CH2-OH $\rightarrow$CH3CH2CH2CH2-Cl + OH - 
C)  CH3S -  + CH3CH2CH2-OCH3 $\rightarrow$ CH3S-CH2CH2CH3 + OCH3 - 
D)  All of the above are likely to occur 
E)  None of the above are likely to occur

Question 11

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 12

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 13

Which of these compounds would give the largest E2/SN2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?

Accepted Answer

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

Question 14

What would be the major product obtained when trans-1-bromo-3-methylcyclopentane is allowed to react with NaSH at 25oC?

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 15

SN2 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)  by using a solvent of high polarity. 
D)  by the use of weak nucleophiles. 
E)  by none of the above. 
A)  when tertiary substrates are used. 
B)  by using a high concentration of the nucleophile. 
C)  by using a solvent of high polarity. 
D)  by the use of weak nucleophiles. 
E)  by none of the above.

Question 16

Give a detailed reaction mechanism for the reaction expected to occur when 2-bromo-2-methylpentane is heated with methanol.Draw clear structural formulas of all relevant species and use curved arrows to represent electron flow.Also indicate which step is likely to be rate-determining.

Accepted Answer

The reaction is likely to occur via an E

Question 17

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 18

Predict the product(s)for the following reaction sequence.

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above 
A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above

Question 19

The reaction,   has the following thermodynamic values at 27ºC: $\Delta$H = -75.3 kJ mol-1; $\Delta$S = 54.4 J K-1 mol-1.What is the value of $\Delta$G for this reaction?

Accepted Answer

A)  -73.8 kJ mol-1 
B)  -76.8 kJ mol-1 
C)  -59.0 kJ mol-1 
D)  +91.6 kJ mol-1 
E)  -91.6 kJ mol-1 
A)  -73.8 kJ mol-1 
B)  -76.8 kJ mol-1 
C)  -59.0 kJ mol-1 
D)  +91.6 kJ mol-1 
E)  -91.6 kJ mol-1

Question 20

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

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

Predict the product(s)for the following reaction sequence.

When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether,the product is analyzed to be C5H10O.Propose a likely structure for this product,suggesting a reasonable mechanistic pathway for its formation.

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?

Ambident nucleophiles are ones which can react with a substrate at either of two nucleophilic sites.Which of the following is not an ambident nucleophile?

Which is the most reactive nucleophile in DMF (structure shown below)?

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

Select the rate law for the following reaction,e.g. , CH3CH2CH2CHBrCH3 + OH - →\rightarrow→ CH3CH2CH2CHOHCH3 + X - ( RBr )

Heating tert-butyl chloride with 1.0 M NaOH in a mixture of water and methanol would yield mainly:

Which nucleophilic substitution reaction would be likely to occur (although probably not in excellent yield,due to competing elimination)?

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?

Which of these compounds would give the largest E2/SN2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?

What would be the major product obtained when trans-1-bromo-3-methylcyclopentane is allowed to react with NaSH at 25oC?

SN2 reactions of the type,Nu- + RL →\rightarrow→ Nu-R + L-, are favored:

Give a detailed reaction mechanism for the reaction expected to occur when 2-bromo-2-methylpentane is heated with methanol.Draw clear structural formulas of all relevant species and use curved arrows to represent electron flow.Also indicate which step is likely to be rate-determining.

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

Predict the product(s)for the following reaction sequence.

The reaction, has the following thermodynamic values at 27ºC: Δ\DeltaΔ H = -75.3 kJ mol-1; Δ\DeltaΔ S = 54.4 J K-1 mol-1.What is the value of Δ\DeltaΔ G for this reaction?

What would be the major product(s)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

When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether,the product is analyzed to be C₅H₁₀O.Propose a likely structure for this product,suggesting a reasonable mechanistic pathway for its formation.

Select the rate law for the following reaction,e.g. , CH₃CH₂CH₂CHBrCH₃ + OH ^- $\rightarrow$ CH₃CH₂CH₂CHOHCH₃ + X ^- ( RBr )

Which of these compounds would give the largest E2/S_N2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?

What would be the major product obtained when trans-1-bromo-3-methylcyclopentane is allowed to react with NaSH at 25^oC?

S_N2 reactions of the type,Nu^- + RL $\rightarrow$ Nu-R + L^-,are favored: