Question 1

Draw the potential energy diagram an exothermic SN1 reaction.

Accepted Answer

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

Question 2

Provide an IUPAC name for the following compound.

Accepted Answer

E-4-methyl

Question 3

What is the degree of substitution of the following alkene?

Accepted Answer

A) monosubstituted 
B)  disubstituted 
C)  trisubstituted 
D)  tetrasubstituted 
A) monosubstituted 
B)  disubstituted 
C)  trisubstituted 
D)  tetrasubstituted

Question 4

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

The answer of Provide the reagents necessary to carry out...

Question 5

Predict the product for the following reaction.
(1R, 3S)-1-bromo-3-sec-butylcyclopentane + NaN3

Accepted Answer

Question 6

Predict the product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these

Question 7

What is the IUPAC name for the following compound?

Accepted Answer

A)  1,2-bromocyclopentane 
B)  (1R, 2S)-1,2-dibromocyclopentane 
C)  (1S, 2S)-1,2-dibromocyclopentane 
D)  (1S, 2R)-1,2-dibromocyclopentane 
E)  (1R, 2R)-1,2-dibromocyclopentane 
A)  1,2-bromocyclopentane 
B)  (1R, 2S)-1,2-dibromocyclopentane 
C)  (1S, 2S)-1,2-dibromocyclopentane 
D)  (1S, 2R)-1,2-dibromocyclopentane 
E)  (1R, 2R)-1,2-dibromocyclopentane

Question 8

Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide?

Accepted Answer

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

Question 9

What is the degree of substitution of the following alkene?

Accepted Answer

A) monosubstituted 
B)  disubstituted 
C)  trisubstituted 
D)  tetrasubstituted 
A) monosubstituted 
B)  disubstituted 
C)  trisubstituted 
D)  tetrasubstituted

Question 10

Rank the following from most to least stable.

Accepted Answer

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

Question 11

Rank the following compounds from most to least reactive in an SN2 reaction.

Accepted Answer

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

Question 12

By what mechanism is the following reaction likely to occur?

Accepted Answer

The answer of By what mechanism is the following reaction...

Question 13

Which of the following is the IUPAC name for the following compound?

Accepted Answer

A)  2-ethyl-1,1,3-trimethylbutene 
B)  3-ethyl-2,4-dimethyl-2-pentene 
C)  2,4-dimethylhexene 
D)  4-ethyl-1,3-dimethyl-3-pentene 
A)  2-ethyl-1,1,3-trimethylbutene 
B)  3-ethyl-2,4-dimethyl-2-pentene 
C)  2,4-dimethylhexene 
D)  4-ethyl-1,3-dimethyl-3-pentene

Question 14

Is the geometry of the following alkene -- E, Z, or neither?

Accepted Answer

The answer of Is the geometry of the following alkene...

Question 15

By what mechanism is the following reaction likely to occur?

Accepted Answer

The answer of By what mechanism is the following reaction...

Question 16

Identify the methylating agent used in biological systems.

Accepted Answer

A)  methyl iodide 
B)  S-adenosylmethionine 
C)  methylalanine 
D)  methylproline 
E)  methyl bromide 
A)  methyl iodide 
B)  S-adenosylmethionine 
C)  methylalanine 
D)  methylproline 
E)  methyl bromide

Question 17

Draw the major product of the following reaction.

Accepted Answer

The answer of Draw the major product of the following...

Question 18

Which of the following is a weakest nucleophile in a polar protic solvent?

Accepted Answer

A)  F- 
B)  Cl- 
C)  Br- 
D)  I- 
E)  All of these 
A)  F- 
B)  Cl- 
C)  Br- 
D)  I- 
E)  All of these

Question 19

Draw the mechanism and product for the following elimination.

Accepted Answer

The answer of Draw the mechanism and product for the...

Question 20

How would you change the following reaction conditions to favor an E1 mechanism?

Accepted Answer

The answer of How would you change the following reaction...

Exam 7: Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Draw the potential energy diagram an exothermic SN1 reaction.

Provide an IUPAC name for the following compound.

What is the degree of substitution of the following alkene?

Provide the reagents necessary to carry out the following conversion.

Predict the product for the following reaction. (1R, 3S)-1-bromo-3-sec-butylcyclopentane + NaN3

Predict the product for the following reaction.

What is the IUPAC name for the following compound?

Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide?

What is the degree of substitution of the following alkene?

Rank the following from most to least stable.

Rank the following compounds from most to least reactive in an SN2 reaction.

By what mechanism is the following reaction likely to occur?

Which of the following is the IUPAC name for the following compound?

Is the geometry of the following alkene -- E, Z, or neither?

By what mechanism is the following reaction likely to occur?

Identify the methylating agent used in biological systems.

Draw the major product of the following reaction.

Which of the following is a weakest nucleophile in a polar protic solvent?

Draw the mechanism and product for the following elimination.

How would you change the following reaction conditions to favor an E1 mechanism?

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Draw the potential energy diagram an exothermic S_N1 reaction.

Predict the product for the following reaction. (1R, 3S)-1-bromo-3-sec-butylcyclopentane + NaN₃

Rank the following compounds from most to least reactive in an S_N2 reaction.