Question 1

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 A

Question 2

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 C

Question 3

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 C

Question 4

What is the IUPAC name of the following compound?

Accepted Answer

A) 2-Bromo-5-methyloctane 
B) 2-Bromo-3-methylheptane 
C) 2-Bromo-5-methylheptane 
D) 6-Bromo-3-methylheptane 
A) 2-Bromo-5-methyloctane 
B) 2-Bromo-3-methylheptane 
C) 2-Bromo-5-methylheptane 
D) 6-Bromo-3-methylheptane

Question 5

Rank the following in order of increasing leaving group ability,putting the worst leaving group first.

Accepted Answer

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

Question 6

What is the IUPAC name of the following compound?

Accepted Answer

A) 2-Bromo-5,5-dimethylheptane 
B) 3,3-Dimethyl-6-bromoheptane 
C) 6-Bromo-3,3-dimethylheptane 
D) 2-Bromo-5,5-dimethyloctane 
A) 2-Bromo-5,5-dimethylheptane 
B) 3,3-Dimethyl-6-bromoheptane 
C) 6-Bromo-3,3-dimethylheptane 
D) 2-Bromo-5,5-dimethyloctane

Question 7

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,H2O 
B) SN1,DMF 
C) SN2,H2O 
D) SN2,DMF 
A) SN1,H2O 
B) SN1,DMF 
C) SN2,H2O 
D) SN2,DMF

Question 8

Which of the following is a polar aprotic solvent?

Accepted Answer

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

Question 9

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 10

Which of the following structures have the correct common name?

Accepted Answer

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

Question 11

What is the IUPAC name of the following compound?

Accepted Answer

A) trans-4-Methylcyclohexyl chloride 
B) trans-p-Chloromethylcyclohexane 
C) trans-4-Methyl-1-chlorocyclohexane 
D) trans-1-Chloro-4-methylcyclohexane 
A) trans-4-Methylcyclohexyl chloride 
B) trans-p-Chloromethylcyclohexane 
C) trans-4-Methyl-1-chlorocyclohexane 
D) trans-1-Chloro-4-methylcyclohexane

Question 12

What is the rate-determining step of an SN1 reaction mechanism?

Accepted Answer

A) Reaction of the nucleophile with the carbocation to form the product. 
B) Breaking the bond between the carbon and the leaving group to generate a carbocation. 
C) Attack of the nucleophile on the substrate to generate a pentavalent carbon. 
D) None of these. 
A) Reaction of the nucleophile with the carbocation to form the product. 
B) Breaking the bond between the carbon and the leaving group to generate a carbocation. 
C) Attack of the nucleophile on the substrate to generate a pentavalent carbon. 
D) None of these.

Question 13

The reaction of what nucleophile and substrate is represented by the following transition state?

Accepted Answer

A) Methanol with 2-bromopropane 
B) Methoxide with 2-bromopropane 
C) Methoxide with 1-bromopropane 
D) Methanol with 1-bromopropane 
A) Methanol with 2-bromopropane 
B) Methoxide with 2-bromopropane 
C) Methoxide with 1-bromopropane 
D) Methanol with 1-bromopropane

Question 14

Identify the nucleophile and type of substitution reaction in the following:

Accepted Answer

A) CN-,Sn1 
B) CN-,Sn2 
C) Br-,Sn1 
D) Br-,Sn2 
A) CN-,Sn1 
B) CN-,Sn2 
C) Br-,Sn1 
D) Br-,Sn2

Question 15

What is the IUPAC name of the following compound?

Accepted Answer

A) (R)-3-Bromo-1-methylcyclohexene 
B) (S)-3-Bromo-1-methylcyclohexene 
C) (S)-1-Bromo-3-methyl-2-cyclohexene 
D) (R)-1-Bromo-3-methyl-2-cyclohexene 
A) (R)-3-Bromo-1-methylcyclohexene 
B) (S)-3-Bromo-1-methylcyclohexene 
C) (S)-1-Bromo-3-methyl-2-cyclohexene 
D) (R)-1-Bromo-3-methyl-2-cyclohexene

Question 16

Rank the following in order of decreasing leaving group ability,putting the best first.

Accepted Answer

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

Question 17

Which of the following statements is not true?

Accepted Answer

A) All good leaving groups are weak bases with strong conjugate acids. 
B) Left-to-right across a row of the periodic table,leaving group ability increases. 
C) Down a column of the periodic table,leaving group ability increases. 
D) Equilibrium favors the products of the nucleophilic substitution when the leaving group is a stronger base than the nucleophile. 
A) All good leaving groups are weak bases with strong conjugate acids. 
B) Left-to-right across a row of the periodic table,leaving group ability increases. 
C) Down a column of the periodic table,leaving group ability increases. 
D) Equilibrium favors the products of the nucleophilic substitution when the leaving group is a stronger base than the nucleophile.

Question 18

Rank the following molecules in order of increasing polarity,putting the least polar first.

Accepted Answer

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

Question 19

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 20

Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br,(CH3)2CHCH2Br,CH3CH2CH(CH3)Br,(CH3)3CBr

Accepted Answer

A) CH3CH2CH2CH2Br 
B) (CH3)2CHCH2Br 
C) CH3CH2CH(CH3)Br 
D) (CH3)3CBr 
A) CH3CH2CH2CH2Br 
B) (CH3)2CHCH2Br 
C) CH3CH2CH(CH3)Br 
D) (CH3)3CBr

Exam 7: Alkyl Halides and Nucleophilic Substitution

What is the IUPAC name of the following compound?

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

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

What is the IUPAC name of the following compound?

Rank the following in order of increasing leaving group ability,putting the worst leaving group first.

What is the IUPAC name of the following compound?

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.

Which of the following is a polar aprotic solvent?

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

Which of the following structures have the correct common name?

What is the IUPAC name of the following compound?

What is the rate-determining step of an SN1 reaction mechanism?

The reaction of what nucleophile and substrate is represented by the following transition state?

Identify the nucleophile and type of substitution reaction in the following:

What is the IUPAC name of the following compound?

Rank the following in order of decreasing leaving group ability,putting the best first.

Which of the following statements is not true?

Rank the following molecules in order of increasing polarity,putting the least polar first.

What is the IUPAC name of the following compound?

Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br,(CH3)2CHCH2Br,CH3CH2CH(CH3)Br,(CH3)3CBr

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

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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

What is the rate-determining step of an S_N1 reaction mechanism?

Which of the following alkyl halides would react the fastest with H₂O in S_N1 reaction? CH₃CH₂CH₂CH₂Br,(CH₃)₂CHCH₂Br,CH₃CH₂CH(CH₃)Br,(CH₃)₃CBr