Question 1

What is the IUPAC name of the following compound?

Accepted Answer

A) (1R,3R)-1-bromo-3-isopropylcyclopentane 
B) (1R,3S)-1-bromo-3-isopropylcyclopentane 
C) (1S,3R)-1-bromo-3-isopropylcyclopentane 
D) (1S,3S)-1-bromo-3-isopropylcyclopentane 
A) (1R,3R)-1-bromo-3-isopropylcyclopentane 
B) (1R,3S)-1-bromo-3-isopropylcyclopentane 
C) (1S,3R)-1-bromo-3-isopropylcyclopentane 
D) (1S,3S)-1-bromo-3-isopropylcyclopentane

Question 2

What is the IUPAC name of the following compound?

Accepted Answer

A) (
E) -2-Bromo-3,4-dimethyl-2-pentene 
B) (Z)-1-Bromo-1,2,3-trimethyl-1-butene 
C) (Z)-2-Bromo-3,4-dimethyl-2-pentene 
D) (
E) -1-Bromo-1,2,3-trimethyl-1-butene 
A) (
E) -2-Bromo-3,4-dimethyl-2-pentene 
B) (Z)-1-Bromo-1,2,3-trimethyl-1-butene 
C) (Z)-2-Bromo-3,4-dimethyl-2-pentene 
D) (
E) -1-Bromo-1,2,3-trimethyl-1-butene

Question 3

Rank the following carbocations in order of decreasing stability,putting the most stable first.

Accepted Answer

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

Question 4

Rank the following in order of increasing nucleophilicity,putting the least nucleophilic first.

Accepted Answer

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

Question 5

What is the product of the nucleophilic substitution reaction shown below?

Accepted Answer

A) Only I 
B) Only II 
C) I and II 
D) None 
A) Only I 
B) Only II 
C) I and II 
D) None

Question 6

Which of the following alkyl halides is a primary alkyl halide?

Accepted Answer

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

Question 7

Which of the following solvents is not a polar protic solvent?

Accepted Answer

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

Question 8

Which of the following is not a characteristic of an SN1 reaction?

Accepted Answer

A) The rate is proportional to the concentration of substrate. 
B) The reaction is favored in polar protic solvents. 
C) The rate is independent of the concentration of the nucleophile. 
D) The electrophilic carbon undergoes inversion of stereochemistry. 
A) The rate is proportional to the concentration of substrate. 
B) The reaction is favored in polar protic solvents. 
C) The rate is independent of the concentration of the nucleophile. 
D) The electrophilic carbon undergoes inversion of stereochemistry.

Question 9

Which of the following statements is not true?

Accepted Answer

A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide. 
B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases. 
C) Sterically hindered bases are also called nonnucleophilic bases. 
D) Steric hindrance decreases basicity but not nucleophilicity. 
A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide. 
B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases. 
C) Sterically hindered bases are also called nonnucleophilic bases. 
D) Steric hindrance decreases basicity but not nucleophilicity.

Question 10

What is the IUPAC name of the following compound?

Accepted Answer

A) (R)-3-Chloro-6-ethyloctane 
B) (S)-3-Chloro-6-ethyloctane 
C) (S)-6-Chloro-3-ethyloctane 
D) (R)-6-Chloro-3-ethyloctane 
A) (R)-3-Chloro-6-ethyloctane 
B) (S)-3-Chloro-6-ethyloctane 
C) (S)-6-Chloro-3-ethyloctane 
D) (R)-6-Chloro-3-ethyloctane

Question 11

What is the IUPAC name of the following compound?

Accepted Answer

A) 2-Chloro-4-isopropyl-2,6-dimethyloctane 
B) 2-Chloro-4-isopropyl-2,7-dimethylnonane 
C) 2,6-Dimethyl-2-chloro-4-isopropyloctane 
D) 7-Chloro-5-isopropyl-3,7-dimethyloctane 
A) 2-Chloro-4-isopropyl-2,6-dimethyloctane 
B) 2-Chloro-4-isopropyl-2,7-dimethylnonane 
C) 2,6-Dimethyl-2-chloro-4-isopropyloctane 
D) 7-Chloro-5-isopropyl-3,7-dimethyloctane

Question 12

The reaction of bromoethane with sodium acetate affords the substitution product methyl acetate.What is the effect of doubling the concentration of sodium acetate on the rate of the reaction?

Accepted Answer

A) The rate remains the same. 
B) The rate decreases by a factor of 2. 
C) The rate increases by a factor of 2. 
D) The rate increases by a factor of 4. 
A) The rate remains the same. 
B) The rate decreases by a factor of 2. 
C) The rate increases by a factor of 2. 
D) The rate increases by a factor of 4.

Question 13

Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions is true?

Accepted Answer

A) Involves one step and occurs with retention of configuration. 
B) Involves two steps and occurs with inversion of configuration. 
C) Involves one step and occurs with inversion of configuration. 
D) Involves one step and occurs with racemization. 
A) Involves one step and occurs with retention of configuration. 
B) Involves two steps and occurs with inversion of configuration. 
C) Involves one step and occurs with inversion of configuration. 
D) Involves one step and occurs with racemization.

Question 14

Pick the solvent that gives the fastest SN2 reaction between CH2CH2Br and -OCH3.

Accepted Answer

A) CH2CH2OH 
B) CH3OH 
C) DMSO 
D) H2O 
A) CH2CH2OH 
B) CH3OH 
C) DMSO 
D) H2O

Question 15

Which of the following statements is not true?

Accepted Answer

A) In polar protic solvents,nucleophilicity decreases down a column of the periodic table as the size of the anion increases. 
B) Nucleophilicity is affected by the solvent used in a substitution reaction. 
C) Polar protic solvents are capable of intermolecular hydrogen bonding. 
D) Polar protic solvents solvate both cations and anions. 
A) In polar protic solvents,nucleophilicity decreases down a column of the periodic table as the size of the anion increases. 
B) Nucleophilicity is affected by the solvent used in a substitution reaction. 
C) Polar protic solvents are capable of intermolecular hydrogen bonding. 
D) Polar protic solvents solvate both cations and anions.

Question 16

Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the SN1 or SN2 mechanism?

Accepted Answer

A) They don't undergo SN1 reactions because a higher percent s-character makes the bond longer and stronger. 
B) They don't undergo SN2 reactions because a higher percent s-character makes the bond shorter and stronger. 
C) They don't undergo SN2 reactions because heterolysis of the C-X bond forms a highly unstable carbocation. 
D) They don't undergo SN1 reactions because the carbocation is highly electronegative. 
A) They don't undergo SN1 reactions because a higher percent s-character makes the bond longer and stronger. 
B) They don't undergo SN2 reactions because a higher percent s-character makes the bond shorter and stronger. 
C) They don't undergo SN2 reactions because heterolysis of the C-X bond forms a highly unstable carbocation. 
D) They don't undergo SN1 reactions because the carbocation is highly electronegative.

Question 17

Rank the following halides in order of decreasing polarity,putting the most polar first.

Accepted Answer

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

Question 18

Which of the following statements about the reactions of alkyl halides is true?

Accepted Answer

A) The characteristic reactions of alkyl halides are addition and elimination. 
B) The characteristic reactions of alkyl halides are addition and substitution. 
C) The characteristic reactions of alkyl halides are elimination and substitution. 
D) The characteristic reactions of alkyl halides are oxidation and reduction. 
A) The characteristic reactions of alkyl halides are addition and elimination. 
B) The characteristic reactions of alkyl halides are addition and substitution. 
C) The characteristic reactions of alkyl halides are elimination and substitution. 
D) The characteristic reactions of alkyl halides are oxidation and reduction.

Question 19

Which of the following alkyl halides is a secondary alkyl halide?

Accepted Answer

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

Question 20

For the following reaction,use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs.Then determine which solvent affords the faster reaction.

Accepted Answer

A) SN1,CH3OH 
B) SN1,DMSO 
C) SN2,CH3OH 
D) SN2,DMSO 
A) SN1,CH3OH 
B) SN1,DMSO 
C) SN2,CH3OH 
D) SN2,DMSO

Exam 7: Alkyl Halides and Nucleophilic Substitution

What is the IUPAC name of the following compound?

What is the IUPAC name of the following compound?

Rank the following carbocations in order of decreasing stability,putting the most stable first.

Rank the following in order of increasing nucleophilicity,putting the least nucleophilic first.

What is the product of the nucleophilic substitution reaction shown below?

Which of the following alkyl halides is a primary alkyl halide?

Which of the following solvents is not a polar protic solvent?

Which of the following is not a characteristic of an SN1 reaction?

Which of the following statements is not true?

What is the IUPAC name of the following compound?

What is the IUPAC name of the following compound?

The reaction of bromoethane with sodium acetate affords the substitution product methyl acetate.What is the effect of doubling the concentration of sodium acetate on the rate of the reaction?

Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions is true?

Pick the solvent that gives the fastest SN2 reaction between CH2CH2Br and -OCH3.

Which of the following statements is not true?

Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the SN1 or SN2 mechanism?

Rank the following halides in order of decreasing polarity,putting the most polar first.

Which of the following statements about the reactions of alkyl halides is true?

Which of the following alkyl halides is a secondary alkyl halide?

For the following reaction,use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs.Then determine which solvent affords the faster reaction.

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Elimination Reactions

Alcohols,ethers,and Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation,resonance,and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

Which of the following is not a characteristic of an S_N1 reaction?

Which of the following statements about the S_N2 mechanism for nucleophilic substitution reactions is true?

Pick the solvent that gives the fastest S_N2 reaction between CH₂CH₂Br and ^-OCH₃.

Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the S_N1 or S_N2 mechanism?