Question 1

What is the electrophile in the following reaction?

Accepted Answer

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

Question 2

Which of the following is a secondary alkyl halide?

Accepted Answer

A)  (CH3)2CHCH2Cl 
B)  (CH3)2CClCH3 
C)  (CH3)2CHCHClCH3 
D)  (CH3)2CHCH2CCl(CH3)2 
A)  (CH3)2CHCH2Cl 
B)  (CH3)2CClCH3 
C)  (CH3)2CHCHClCH3 
D)  (CH3)2CHCH2CCl(CH3)2

Question 3

Predict the product for the following reaction.
(1R, 3S)-1-bromo-3-sec-butilcyclopentane + NaN3

Accepted Answer

Question 4

What is the correct structure for 2-bromo-3-methylbutane?

Accepted Answer

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

Question 5

What substitution reaction mechanism is most likely for the following conversion?

Accepted Answer

A)  SN1 
B)  SN2 
C)  Either SN1 or SN2 
D)  None of these 
A)  SN1 
B)  SN2 
C)  Either SN1 or SN2 
D)  None of these

Question 6

Predict the product for the following SN2 reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  Both I & II 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  Both I & II

Question 7

Consider the following SN2 reaction,   Assuming no other changes, what is the effect on the rate, if the concentration of 2-bromopentane is doubled and the concentration of CH3CH2COONa is halved?

Accepted Answer

A)  No effect 
B)  It would double the rate 
C)  It would triple the rate 
D)  It would increase four times 
E)  It would reduce by half 
A)  No effect 
B)  It would double the rate 
C)  It would triple the rate 
D)  It would increase four times 
E)  It would reduce by half

Question 8

Which of the following compounds has the best leaving group?

Accepted Answer

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

Question 9

Draw the transition state for the following reaction.
(S)-1-iodo-3-methylpentane +NaSCH3

Accepted Answer

Question 10

Draw the transition state for the following reaction.

Accepted Answer

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

Question 11

Which of the following alkyl halides will undergo the slowest SN2 reaction?

Accepted Answer

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

Question 12

Which of the following potential energy diagram represent an exothermic SN1 reaction?

Accepted Answer

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

Question 13

Which of the following is a strong nucleophile?

Accepted Answer

A)  OH- 
B)  H2O 
C)  CH3OH 
D)  NH4+ 
E)  All of these 
A)  OH- 
B)  H2O 
C)  CH3OH 
D)  NH4+ 
E)  All of these

Question 14

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  NaCl in water 
B)  NaCl in ether 
C)  HCl in water 
D)  TsCl/pyridine followed by NaCl 
A)  NaCl in water 
B)  NaCl in ether 
C)  HCl in water 
D)  TsCl/pyridine followed by NaCl

Question 15

Rank the following compounds from most to least reactive in an SN2 reaction.

Accepted Answer

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

Question 16

Which of the following is the rate equation for the following reaction? CH3CH2CH2CHBrCH3 + NaN3$\rightarrow$CH3CH2CH2CHN3CH3 + NaBr

Accepted Answer

A)  Rate = k[CH3CH2CH2CHBrCH3] 
B)  Rate = k[NaN3] 
C)  Rate = k[CH3CH2CH2CHBrCH3] [NaBr] 
D)  Rate = k[CH3CH2CH2CHBrCH3] [NaN3] 
E)  Rate = k[CH3CH2CH2CHBrCH3]2 [NaN3] 
A)  Rate = k[CH3CH2CH2CHBrCH3] 
B)  Rate = k[NaN3] 
C)  Rate = k[CH3CH2CH2CHBrCH3] [NaBr] 
D)  Rate = k[CH3CH2CH2CHBrCH3] [NaN3] 
E)  Rate = k[CH3CH2CH2CHBrCH3]2 [NaN3]

Question 17

Which of the following compounds will undergo the fastest SN1 reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  Both I & IV 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  Both I & IV

Question 18

Predict the major product for the following reaction.

Accepted Answer

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

Question 19

Which of the following is a protic solvent?

Accepted Answer

A)  I- 
B)  II- 
C)  III 
D)  IV 
E)  none of these 
A)  I- 
B)  II- 
C)  III 
D)  IV 
E)  none of these

Question 20

Provide a curved arrow mechanism for the following reaction.

Accepted Answer

The answer of Provide a curved arrow mechanism for the...

Exam 7: Substitution Reactions

What is the electrophile in the following reaction?

Which of the following is a secondary alkyl halide?

Predict the product for the following reaction. (1R, 3S)-1-bromo-3-sec-butilcyclopentane + NaN3

What is the correct structure for 2-bromo-3-methylbutane?

What substitution reaction mechanism is most likely for the following conversion?

Predict the product for the following SN2 reaction.

Consider the following SN2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of 2-bromopentane is doubled and the concentration of CH3CH2COONa is halved?

Which of the following compounds has the best leaving group?

Draw the transition state for the following reaction. (S)-1-iodo-3-methylpentane +NaSCH3

Draw the transition state for the following reaction.

Which of the following alkyl halides will undergo the slowest SN2 reaction?

Which of the following potential energy diagram represent an exothermic SN1 reaction?

Which of the following is a strong nucleophile?

Provide the reagents necessary to carry out the following conversion.

Rank the following compounds from most to least reactive in an SN2 reaction.

Which of the following is the rate equation for the following reaction? CH3CH2CH2CHBrCH3 + NaN3 →\rightarrow→ CH3CH2CH2CHN3CH3 + NaBr

Which of the following compounds will undergo the fastest SN1 reaction?

Predict the major product for the following reaction.

Which of the following is a protic solvent?

Provide a curved arrow mechanism for the following reaction.

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkenes: Structure and Preparation Via Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Predict the product for the following reaction. (1R, 3S)-1-bromo-3-sec-butilcyclopentane + NaN₃

Predict the product for the following S_N2 reaction.

Consider the following S_N2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of 2-bromopentane is doubled and the concentration of CH₃CH₂COONa is halved?

Draw the transition state for the following reaction. (S)-1-iodo-3-methylpentane +NaSCH₃

Which of the following alkyl halides will undergo the slowest S_N2 reaction?

Which of the following potential energy diagram represent an exothermic S_N1 reaction?

Rank the following compounds from most to least reactive in an S_N2 reaction.

Which of the following is the rate equation for the following reaction? CH₃CH₂CH₂CHBrCH₃ + NaN₃ $\rightarrow$ CH₃CH₂CH₂CHN₃CH₃ + NaBr

Which of the following compounds will undergo the fastest S_N1 reaction?