Question 1

Explain why SN2 reactions proceed faster in the solvent dimethylsulfoxide than in ethanol?
CH3SOCH3 CH3CH2OH
dimethlysolfoxide ethanol

Accepted Answer

Dimethlysulfoxide is an aproti

Question 2

Provide the major organic product(s)of the reaction shown.

Accepted Answer

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

Question 3

Identify the halide(s)that react in a SN2 reaction.

Accepted Answer

A) benzyl bromide 
B) bromobenzene 
C) 1-bromo-1-butene 
D) 1-bromo-2-butene 
E) 2-bromo-2-phenylpropane 
A) benzyl bromide 
B) bromobenzene 
C) 1-bromo-1-butene 
D) 1-bromo-2-butene 
E) 2-bromo-2-phenylpropane

Question 4

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 5

Which of the following is the strongest nucleophile in an aqueous solution?

Accepted Answer

A) HO- 
B) F- 
C) Cl- 
D) Br- 
E) I- 
A) HO- 
B) F- 
C) Cl- 
D) Br- 
E) I-

Question 6

Identify the alkyl halide that reacts the fastest in an SN1 reaction.

Accepted Answer

A) 2-chloropropane 
B) 2-bromopropane 
C) 2-fluoropropane 
D) 2-iodopropane 
A) 2-chloropropane 
B) 2-bromopropane 
C) 2-fluoropropane 
D) 2-iodopropane

Question 7

Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above SN1 reaction?

Accepted Answer

A) no change 
B) doubles the rate 
C) triples the rate 
D) quadruples the rate 
E) rate is halved 
A) no change 
B) doubles the rate 
C) triples the rate 
D) quadruples the rate 
E) rate is halved

Question 8

Do all primary alkyl iodides undergo SN2 reactions with sodium cyanide in DMSO at identical rates? Explain.

Accepted Answer

No. All primary iodides are no

Question 9

Give the name(s)of the product(s)for the following SN2 reaction.

Accepted Answer

A) (S)-2-hexanol 
B) (R)-2-hexanol 
C) (S)-3-hexanol 
D) (R)-3-hexanol 
A) (S)-2-hexanol 
B) (R)-2-hexanol 
C) (S)-3-hexanol 
D) (R)-3-hexanol

Question 10

Which of the following species is most reactive in an SN2 reaction?

Accepted Answer

A) CH3CH2-Cl 
B) CH3CH2-Br 
C) CH3CH2-I 
D) CH3CH2-F 
E) CH3CH2-OH 
A) CH3CH2-Cl 
B) CH3CH2-Br 
C) CH3CH2-I 
D) CH3CH2-F 
E) CH3CH2-OH

Question 11

Which of the following bromides reacts readily via an SN2 reaction with NaN3?

Accepted Answer

A) C6H5Br 
B) CH3CH2CH=CHBr 
C) (C6H5)3CBr 
D) (CH3)3CCH2CH2CH2Br 
E) 1-bromo-1-methylcyclohexane 
A) C6H5Br 
B) CH3CH2CH=CHBr 
C) (C6H5)3CBr 
D) (CH3)3CCH2CH2CH2Br 
E) 1-bromo-1-methylcyclohexane

Question 12

Assuming no other changes, what is the effect of doubling both the alkyl halide and the nucleophile concentrations in the above reaction?

Accepted Answer

A) no change 
B) doubles the rate 
C) triples the rate 
D) quadruples the rate 
E) rate is halved 
A) no change 
B) doubles the rate 
C) triples the rate 
D) quadruples the rate 
E) rate is halved

Question 13

Provide the major organic product(s)of the reaction shown.

Accepted Answer

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

Question 14

Give the SN2product(s)for the reaction of (R)-2-bromopentane with an excess of sodium methoxide.

Accepted Answer

A) (S)-2-methoxypentane 
B) (R)-2-methoxypentane 
C) (S)-2-ethoxypentane 
D) (R)-2-ethoxypentane 
E) (R)-2-pentanol 
A) (S)-2-methoxypentane 
B) (R)-2-methoxypentane 
C) (S)-2-ethoxypentane 
D) (R)-2-ethoxypentane 
E) (R)-2-pentanol

Question 15

Which of the following can't undergo nucleophilic substitution reactions?

Accepted Answer

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

Question 16

When (S)-1-bromo-1 phenylethane undergoes an SN1 reaction with methanethiol (CH3SH), the product is the compound shown. What is/are the configuration(s)of the product obtained from this reaction?

Accepted Answer

A) S only 
B) R only 
C) a mixture of the enantiomers, with slightly more S than R 
D) a mixture of the enantiomers, with slightly more R than S 
A) S only 
B) R only 
C) a mixture of the enantiomers, with slightly more S than R 
D) a mixture of the enantiomers, with slightly more R than S

Question 17

Which of the following carbocations does not rearrange?

Accepted Answer

A)    
B)    
C)    
D)    
E) all the above 
A)    
B)    
C)    
D)    
E) all the above

Question 18

Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

Accepted Answer

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

Exam 9: Substitution Reactions of Alkyl Halides

Explain why SN2 reactions proceed faster in the solvent dimethylsulfoxide than in ethanol? CH3SOCH3 CH3CH2OH dimethlysolfoxide ethanol

Provide the major organic product(s)of the reaction shown.

Identify the halide(s)that react in a SN2 reaction.

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

Which of the following is the strongest nucleophile in an aqueous solution?

Identify the alkyl halide that reacts the fastest in an SN1 reaction.

Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above SN1 reaction?

Do all primary alkyl iodides undergo SN2 reactions with sodium cyanide in DMSO at identical rates? Explain.

Give the name(s)of the product(s)for the following SN2 reaction.

Which of the following species is most reactive in an SN2 reaction?

Which of the following bromides reacts readily via an SN2 reaction with NaN3?

Assuming no other changes, what is the effect of doubling both the alkyl halide and the nucleophile concentrations in the above reaction?

Provide the major organic product(s)of the reaction shown.

Give the SN2product(s)for the reaction of (R)-2-bromopentane with an excess of sodium methoxide.

Which of the following can't undergo nucleophilic substitution reactions?

When (S)-1-bromo-1 phenylethane undergoes an SN1 reaction with methanethiol (CH3SH), the product is the compound shown. What is/are the configuration(s)of the product obtained from this reaction?

Which of the following carbocations does not rearrange?

Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

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

Explain why S_N2 reactions proceed faster in the solvent dimethylsulfoxide than in ethanol? CH₃SOCH₃ CH₃CH₂OH dimethlysolfoxide ethanol

Identify the halide(s)that react in a S_N2 reaction.

Identify the alkyl halide that reacts the fastest in an S_N1 reaction.

Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above S_N1 reaction?

Do all primary alkyl iodides undergo S_N2 reactions with sodium cyanide in DMSO at identical rates? Explain.

Give the name(s)of the product(s)for the following S_N2 reaction.

Which of the following species is most reactive in an S_N2 reaction?

Which of the following bromides reacts readily via an S_N2 reaction with NaN₃?

Give the S_N2product(s)for the reaction of (R)-2-bromopentane with an excess of sodium methoxide.

When (S)-1-bromo-1 phenylethane undergoes an S_N1 reaction with methanethiol (CH₃SH), the product is the compound shown. What is/are the configuration(s)of the product obtained from this reaction?