Question 1

Give the name(s)of the product(s)for the following SN1 reactions.   
A)(S)-2-hexanol
B)(R)-2-hexanol
C)(S)-3-hexanol
D)(R)-3-hexanol

Accepted Answer

Question 2

Which halide reacts most rapidly via an SN2 mechanism?

Accepted Answer

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

Question 3

In the SN1 hydrolysis mechanism of (CH3)3CBr, there are ________ elementary steps, ________ distinct transition states, and ________ distinct intermediates.

Accepted Answer

A) 2, 2, 2 
B) 2, 2, 3 
C) 2, 3, 2 
D) 3, 2, 3 
E) 3, 3, 2 
A) 2, 2, 2 
B) 2, 2, 3 
C) 2, 3, 2 
D) 3, 2, 3 
E) 3, 3, 2

Question 4

Provide the structure of the major organic product of the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 5

Which of the following carbocations is the most stable?

Accepted Answer

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

Question 6

Which of the following iodides undergoes SN1 solvolysis in water the fastest?

Accepted Answer

A) 1-iodo-3-methylpentane 
B) 2-iodopentane 
C) 2-iodo-2-methylpentane 
D) 3-iodopentane 
E) 1-iodo-2,2-dimethylpentane 
A) 1-iodo-3-methylpentane 
B) 2-iodopentane 
C) 2-iodo-2-methylpentane 
D) 3-iodopentane 
E) 1-iodo-2,2-dimethylpentane

Question 7

Which halide reacts most rapidly via an SN2 mechanism?

Accepted Answer

A) (CH3)CCH2CH2F 
B) (CH3)CCH2CH2Cl 
C) (CH3)CCH2CH2Br 
D) (CH3)CCH2CH2I 
E) All primary halides react at the same rate in SN2. 
A) (CH3)CCH2CH2F 
B) (CH3)CCH2CH2Cl 
C) (CH3)CCH2CH2Br 
D) (CH3)CCH2CH2I 
E) All primary halides react at the same rate in SN2.

Question 8

Which of the following SN2 reactions is the slowest?

Accepted Answer

A) CH3CH2CHBrCH3 + OH- → CH3CH2CHOHCH3 + Br- 
B) CH3CH2CHBrCH3 + H2O → CH3CH2CHOHCH3 + HBr 
C) CH3CH2CH2CH2Br + OH- → CH3CH2CH2CH2OH + Br- 
D) CH3CH2CH2CH2Br + H2O → CH3CH2CH2CH2OH + HBr 
A) CH3CH2CHBrCH3 + OH- → CH3CH2CHOHCH3 + Br- 
B) CH3CH2CHBrCH3 + H2O → CH3CH2CHOHCH3 + HBr 
C) CH3CH2CH2CH2Br + OH- → CH3CH2CH2CH2OH + Br- 
D) CH3CH2CH2CH2Br + H2O → CH3CH2CH2CH2OH + HBr

Question 9

Provide the major organic product(s)in the reaction below.

Accepted Answer

The answer of Provide the major organic product(s)in the reaction...

Question 10

Provide the structure of the major organic product which results when (S)-2-iodopentane is treated with KCN in DMF.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 11

Which of the following is the best nucleophile in water?

Accepted Answer

A) I- 
B) CH3SCH3 
C) CH3OCH3 
D) Cl- 
A) I- 
B) CH3SCH3 
C) CH3OCH3 
D) Cl-

Question 12

Which of the following carbocations is the least stable?

Accepted Answer

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

Question 13

Give the mechanism.

Accepted Answer

The answer of Give the mechanism.  ...

Question 14

What is the leaving group in the reaction shown below?

Accepted Answer

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

Question 15

Protic and aprotic solvents are very similar as solvents except for their ________.

Accepted Answer

A) polarity 
B) dielectric constant 
C) ability to stabilize anions by hydrogen bonding 
D) ability to stabilize cations by hydrogen bonding 
E) ability to stabilize cations with unshared pairs of electrons 
A) polarity 
B) dielectric constant 
C) ability to stabilize anions by hydrogen bonding 
D) ability to stabilize cations by hydrogen bonding 
E) ability to stabilize cations with unshared pairs of electrons

Question 16

Identify the alkyl halide that reacts the fastest in an SN2 reaction.

Accepted Answer

A) 1-chloropropane 
B) 1-bromopropane 
C) 1-fluoropropane 
D) 1-iodopropane 
A) 1-chloropropane 
B) 1-bromopropane 
C) 1-fluoropropane 
D) 1-iodopropane

Question 17

What type of solvent is best for SN2 reactions which employ anionic nucleophiles: polar, protic solvents; polar, aprotic solvents; or nonpolar solvents? Explain.

Accepted Answer

Polar, aprotic solvents are be

Question 18

The specific rotation of optically pure (R)-sec-butyl alcohol is -13.52°. An optically pure sample of (R)-sec-butyl bromide was converted into the corresponding sec-butyl alcohol via an SN2 reaction. What is the specific rotation of the product, assuming 100% yield?

Accepted Answer

A) -13.52° 
B) between 0° and -13.52° 
C) between 0° and +13.52° 
D) +13.52° 
E) zero 
A) -13.52° 
B) between 0° and -13.52° 
C) between 0° and +13.52° 
D) +13.52° 
E) zero

Question 19

Which of the following SN2 reactions is the slowest?

Accepted Answer

A) CH3CH2CH3Br + HO- → CH3CH2CH3OH + Br- 
B) CH3CH2CH2Cl + HO- → CH3CH2CH2OH + Cl- 
C) CH3CH2CH2I + HO- → CH3CH2CH2OH + I- 
D) CH3CH2CH3F + HO- → CH3CH2CH2OH + F- 
E)    
A) CH3CH2CH3Br + HO- → CH3CH2CH3OH + Br- 
B) CH3CH2CH2Cl + HO- → CH3CH2CH2OH + Cl- 
C) CH3CH2CH2I + HO- → CH3CH2CH2OH + I- 
D) CH3CH2CH3F + HO- → CH3CH2CH2OH + F- 
E)

Question 20

Which of the following statements concerning SN2 reactions of alkyl halides is not correct?

Accepted Answer

A) The rate of reaction depends on the concentration of the nucleophile. 
B) The rate of reaction depends on the concentration of the alkyl halide. 
C) The rate of reaction of a particular alkyl bromide depends on the steric accessibility of the carbon of the C-Br bond. 
D) All alkyl iodides react more rapidly than all alkyl chlorides. 
E) The rate of reaction depends on the relative nucleophilicity of the nucleophile. 
A) The rate of reaction depends on the concentration of the nucleophile. 
B) The rate of reaction depends on the concentration of the alkyl halide. 
C) The rate of reaction of a particular alkyl bromide depends on the steric accessibility of the carbon of the C-Br bond. 
D) All alkyl iodides react more rapidly than all alkyl chlorides. 
E) The rate of reaction depends on the relative nucleophilicity of the nucleophile.

Exam 9: Substitution Reactions of Alkyl Halides

Give the name(s)of the product(s)for the following SN1 reactions. A)(S)-2-hexanol B)(R)-2-hexanol C)(S)-3-hexanol D)(R)-3-hexanol

Which halide reacts most rapidly via an SN2 mechanism?

In the SN1 hydrolysis mechanism of (CH3)3CBr, there are ________ elementary steps, ________ distinct transition states, and ________ distinct intermediates.

Provide the structure of the major organic product of the following reaction.

Which of the following carbocations is the most stable?

Which of the following iodides undergoes SN1 solvolysis in water the fastest?

Which halide reacts most rapidly via an SN2 mechanism?

Which of the following SN2 reactions is the slowest?

Provide the major organic product(s)in the reaction below.

Provide the structure of the major organic product which results when (S)-2-iodopentane is treated with KCN in DMF.

Which of the following is the best nucleophile in water?

Which of the following carbocations is the least stable?

Give the mechanism.

What is the leaving group in the reaction shown below?

Protic and aprotic solvents are very similar as solvents except for their ________.

Identify the alkyl halide that reacts the fastest in an SN2 reaction.

What type of solvent is best for SN2 reactions which employ anionic nucleophiles: polar, protic solvents; polar, aprotic solvents; or nonpolar solvents? Explain.

The specific rotation of optically pure (R)-sec-butyl alcohol is -13.52°. An optically pure sample of (R)-sec-butyl bromide was converted into the corresponding sec-butyl alcohol via an SN2 reaction. What is the specific rotation of the product, assuming 100% yield?

Which of the following SN2 reactions is the slowest?

Which of the following statements concerning SN2 reactions of alkyl halides is not correct?

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds

Isomers: the Arrangement of Atoms in Space

Alkenes Thermodynamics and Kinetics

Reactions of Alkenes

Reactions of Alkynes Introduction to Multistep Synthesis

Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

Reactions of Alkanes, Radicals

Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions at the Alpha Carbon of Carbonyl Compounds

Reactions of Benzene and Substituted Benzenes

More About Amines Heterocylic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Catalysis

The Organic Mechanisms of the Coenzymes

The Chemistry of Metabolism

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Give the name(s)of the product(s)for the following S_N1 reactions. A)(S)-2-hexanol B)(R)-2-hexanol C)(S)-3-hexanol D)(R)-3-hexanol

Which halide reacts most rapidly via an S_N2 mechanism?

In the S_N1 hydrolysis mechanism of (CH₃)₃CBr, there are elementary steps, distinct transition states, and distinct intermediates.

Which of the following iodides undergoes S_N1 solvolysis in water the fastest?

Which halide reacts most rapidly via an S_N2 mechanism?

Which of the following S_N2 reactions is the slowest?

Identify the alkyl halide that reacts the fastest in an S_N2 reaction.

What type of solvent is best for S_N2 reactions which employ anionic nucleophiles: polar, protic solvents; polar, aprotic solvents; or nonpolar solvents? Explain.

The specific rotation of optically pure (R)-sec-butyl alcohol is -13.52°. An optically pure sample of (R)-sec-butyl bromide was converted into the corresponding sec-butyl alcohol via an S_N2 reaction. What is the specific rotation of the product, assuming 100% yield?

Which of the following S_N2 reactions is the slowest?

Which of the following statements concerning S_N2 reactions of alkyl halides is not correct?