Question 1

Provide the name of the bromoalkane shown below.

Accepted Answer

3-bromo-4-

Question 2

Consider the substitution reaction shown below. By what mechanism will the reaction proceed?

Accepted Answer

A)  SN1 
B)  SN2 
C)  free radical reaction 
D)  There is not enough information to tell. 
A)  SN1 
B)  SN2 
C)  free radical reaction 
D)  There is not enough information to tell.

Question 3

Consider the substitution reaction shown below. By what mechanism will the reaction proceed?

Accepted Answer

A)  SN1 
B)  SN2 
C)  Free radical reaction 
D)  There is not enough information to tell. 
A)  SN1 
B)  SN2 
C)  Free radical reaction 
D)  There is not enough information to tell.

Question 4

Predict the most likely mechanism for the reaction shown below.

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  E1cb 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  E1cb

Question 5

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

Accepted Answer

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

Question 6

When water is shaken with dichloromethane, a two-phase system results. Which compound forms the upper phase? Explain.

Accepted Answer

Water is less dense

Question 7

Circle the protic solvents.

Accepted Answer

The answer of Circle the protic solvents.  ...

Question 8

Propose a mechanism with a hydride shift for the solvolysis reaction below.

Accepted Answer

The answer of Propose a mechanism with a hydride shift...

Question 9

Which of the following is classified as a vinylic halide?

Accepted Answer

A)  CH3CH   CHOH 
B)  CH3CH   CHCl 
C)  CH3CH   CHCH2Cl 
D)  CH3CH2CH2CH2Br 
E)  BrCH2CH   CH2 
A)  CH3CH   CHOH 
B)  CH3CH   CHCl 
C)  CH3CH   CHCH2Cl 
D)  CH3CH2CH2CH2Br 
E)  BrCH2CH   CH2

Question 10

What type of solvent is best for SN2 reactions which employ anionic nucleophiles: polar, protic solvents; polar, aprotic solvents; or nonpolar solvents? Explain.

Accepted Answer

Polar, aprotic solvents are be

Question 11

Which of the following is a vicinal dihalide?

Accepted Answer

A)  cis-1,2-dibromocyclopentane 
B)  3,3-dichloropentane 
C)  trans-1,4-diiodocyclohexane 
D)  isobutyl chloride 
E)  1,3-dibromoheptane 
A)  cis-1,2-dibromocyclopentane 
B)  3,3-dichloropentane 
C)  trans-1,4-diiodocyclohexane 
D)  isobutyl chloride 
E)  1,3-dibromoheptane

Question 12

Provide the structure of 1-bromo-3-methylhexane.

Accepted Answer

The answer of Provide the structure of 1-bromo-3-methylhexane....

Question 13

Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)?
I. Rate = k[base]
II. Rate = k[base][RX]
III. Rate = k[RX]
IV. The reactions occur in two or more distinct steps.
V. Rearrangements are sometimes seen.

Accepted Answer

A)  II and IV 
B)  III and V 
C)  I, IV, and V 
D)  I only 
E)  III, IV, and V 
A)  II and IV 
B)  III and V 
C)  I, IV, and V 
D)  I only 
E)  III, IV, and V

Question 14

Which of the following alkyl chlorides would undergo substitution most rapidly when treated with   
   
or   
Provide the structure of the substitution product.

Accepted Answer

The answer of Which of the following alkyl chlorides would...

Question 15

Although F is more electronegative than Cl, the C-Cl bond has a larger dipole moment than the   
Explain.

Accepted Answer

The bond dipole moment is determined by

Question 16

Name one factor that is favorable for nucleophilicity but not for basicity.

Accepted Answer

The answer of Name one factor that is favorable for...

Question 17

Complete the following SN2 reaction by providing structures for the necessary starting materials.

Accepted Answer

Question 18

When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced.

Accepted Answer

The answer of When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol,...

Question 19

How many distinct alkene products are possible, including stereoisomers, when the alkyl iodide below undergoes E2 elimination?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  5 
A)  1 
B)  2 
C)  3 
D)  4 
E)  5

Question 20

What is Zaitsev's rule?

Accepted Answer

In elimination react

Exam 6: Alkyl Halides; Nucleophilic Substitution

Provide the name of the bromoalkane shown below.

Consider the substitution reaction shown below. By what mechanism will the reaction proceed?

Consider the substitution reaction shown below. By what mechanism will the reaction proceed?

Predict the most likely mechanism for the reaction shown below.

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

When water is shaken with dichloromethane, a two-phase system results. Which compound forms the upper phase? Explain.

Circle the protic solvents.

Propose a mechanism with a hydride shift for the solvolysis reaction below.

Which of the following is classified as a vinylic halide?

What type of solvent is best for SN2 reactions which employ anionic nucleophiles: polar, protic solvents; polar, aprotic solvents; or nonpolar solvents? Explain.

Which of the following is a vicinal dihalide?

Provide the structure of 1-bromo-3-methylhexane.

Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)? I. Rate = k[base] II. Rate = k[base][RX] III. Rate = k[RX] IV. The reactions occur in two or more distinct steps. V. Rearrangements are sometimes seen.

Which of the following alkyl chlorides would undergo substitution most rapidly when treated with or Provide the structure of the substitution product.

Although F is more electronegative than Cl, the C-Cl bond has a larger dipole moment than the Explain.

Name one factor that is favorable for nucleophilicity but not for basicity.

Complete the following SN2 reaction by providing structures for the necessary starting materials.

When 1-bromo-2, 2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced.

How many distinct alkene products are possible, including stereoisomers, when the alkyl iodide below undergoes E2 elimination?

What is Zaitsev's rule?

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

What type of solvent is best for S_N2 reactions which employ anionic nucleophiles: polar, protic solvents; polar, aprotic solvents; or nonpolar solvents? Explain.

Complete the following S_N2 reaction by providing structures for the necessary starting materials.