Question 1

Identify the 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 2

Which of the following SN2 reactions is the fastest?

Accepted Answer

A)    
B) CH3CH2CH2I + HO- → CH3CH2CH2OH + I- 
C)    
D) CH3CH2CH3Br + HO- → CH3CH2CH3OH + Br- 
E) CH3CH2CH2I + H2O → CH3CH2CH2OH + HI 
A)    
B) CH3CH2CH2I + HO- → CH3CH2CH2OH + I- 
C)    
D) CH3CH2CH3Br + HO- → CH3CH2CH3OH + Br- 
E) CH3CH2CH2I + H2O → CH3CH2CH2OH + HI

Question 3

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 4

Which of the following iodides undergoes SN2 reaction with cyanide (CN-)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 5

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

Accepted Answer

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

Question 6

Explain why allyl chloride, shown below, undergoes SN1 reactions even though it is a 1° halide?
CH2
    CHCH2Cl
allyl chloride

Accepted Answer

Allyl chloride forms a relativ

Question 7

Draw the product for the following SN2 reaction.

Accepted Answer

Question 8

Assuming no other changes, what is the effect of doubling both the concentration of the alkyl halide and the nucleophile 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 9

When (S)-2-bromobutane undergoes an SN2 reaction with CH3O-, the product is the compound shown below. What is/are the configuration(s)of the product(s)obtained from this reaction?

Accepted Answer

A) S only 
B) R only 
C) a mixture of enantiomers with more R than S 
D) a mixture of enantiomers with more S than R 
E) equal mixture of R and S 
A) S only 
B) R only 
C) a mixture of enantiomers with more R than S 
D) a mixture of enantiomers with more S than R 
E) equal mixture of R and S

Question 10

Provide the structure of the major organic product which results in the following reaction.

Accepted Answer

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

Question 11

Which of the following is the best leaving group?

Accepted Answer

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

Question 12

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 13

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

Accepted Answer

A) 2-chloro-2-methylpropane 
B) 2-chlorobutane 
C) 1-chlorobutane 
D) chloromethane 
A) 2-chloro-2-methylpropane 
B) 2-chlorobutane 
C) 1-chlorobutane 
D) chloromethane

Question 14

In an SN2 reaction why does the nucleophile attack the carbon on the side opposite the leaving group?

Accepted Answer

Back side attack occurs because the orbi

Question 15

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 16

What product results from the SN2 reaction between (R)-2-chloropentane and hydroxide?

Accepted Answer

A) (R)-2-pentanol 
B) (S)-2-pentanol 
C) racemic pentanol 
D) 1-pentanol 
E) 3-pentanol 
A) (R)-2-pentanol 
B) (S)-2-pentanol 
C) racemic pentanol 
D) 1-pentanol 
E) 3-pentanol

Question 17

Give the name(s)of the product(s)of the SN2 reaction of 3-bromo-2,2-dimethylbutane with hydroxide.

Accepted Answer

A) 2,2-dimethyl-1-butanol 
B) 3,3-dimethyl-2-butanol 
C) 3,3-dimethyl-1-butanol 
D) 2,3-dimethyl-2-butanol 
E) 2,3-dimethyl-1-butanol 
A) 2,2-dimethyl-1-butanol 
B) 3,3-dimethyl-2-butanol 
C) 3,3-dimethyl-1-butanol 
D) 2,3-dimethyl-2-butanol 
E) 2,3-dimethyl-1-butanol

Question 18

What is the nucleophile 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 19

Which of the following are the substitution products of the reaction shown below? CH3CH2Br + -OH → ?

Accepted Answer

A) CH3CH2BrH+ + O- 
B) HOCH2CH2Br 
C) CH3CH2OH + Br- 
D) CH2     CH2 + Br- + H2O 
E) CH2     CHBr + H2O 
A) CH3CH2BrH+ + O- 
B) HOCH2CH2Br 
C) CH3CH2OH + Br- 
D) CH2     CH2 + Br- + H2O 
E) CH2     CHBr + H2O

Question 20

Provide the structure of the major organic product in the following reaction.
(CH3)3N + CH3CH2CH2I →

Accepted Answer

Exam 9: Substitution Reactions of Alkyl Halides

Identify the mechanism.

Which of the following SN2 reactions is the fastest?

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

Which of the following iodides undergoes SN2 reaction with cyanide (CN-)the fastest?

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

Explain why allyl chloride, shown below, undergoes SN1 reactions even though it is a 1° halide? CH2 CHCH2Cl allyl chloride

Draw the product for the following SN2 reaction.

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

When (S)-2-bromobutane undergoes an SN2 reaction with CH3O-, the product is the compound shown below. What is/are the configuration(s)of the product(s)obtained from this reaction?

Provide the structure of the major organic product which results in the following reaction.

Which of the following is the best leaving group?

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

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

In an SN2 reaction why does the nucleophile attack the carbon on the side opposite the leaving group?

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

What product results from the SN2 reaction between (R)-2-chloropentane and hydroxide?

Give the name(s)of the product(s)of the SN2 reaction of 3-bromo-2,2-dimethylbutane with hydroxide.

What is the nucleophile in the reaction shown below?

Which of the following are the substitution products of the reaction shown below? CH3CH2Br + -OH → ?

Provide the structure of the major organic product in the following reaction. (CH3)3N + CH3CH2CH2I →

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

Which of the following S_N2 reactions is the fastest?

Which of the following iodides undergoes S_N2 reaction with cyanide (CN^-)the fastest?

Explain why allyl chloride, shown below, undergoes S_N1 reactions even though it is a 1° halide? CH₂ CHCH₂Cl allyl chloride

Draw the product for the following S_N2 reaction.

When (S)-2-bromobutane undergoes an S_N2 reaction with CH₃O^-, the product is the compound shown below. What is/are the configuration(s)of the product(s)obtained from this reaction?

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

In an S_N2 reaction why does the nucleophile attack the carbon on the side opposite the leaving group?

What product results from the S_N2 reaction between (R)-2-chloropentane and hydroxide?

Give the name(s)of the product(s)of the S_N2 reaction of 3-bromo-2,2-dimethylbutane with hydroxide.

Which of the following are the substitution products of the reaction shown below? CH₃CH₂Br + ^-OH → ?

Provide the structure of the major organic product in the following reaction. (CH₃)₃N + CH₃CH₂CH₂I →