Question 1

Which of the following reactions is classified as a Williamson ether synthesis?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 2

Di-n-pentyl ether can be converted to 1-bromopentane by treatment with HBr through essentially a(n) ________ mechanism.

Accepted Answer

A)  SN2 
B)  SN1 
C)  E2 
D)  E1 
E)  ring opening 
A)  SN2 
B)  SN1 
C)  E2 
D)  E1 
E)  ring opening

Question 3

When trans-hex-3-ene is treated with PhCO3H, the major organic product is:

Accepted Answer

A)  a meso epoxide. 
B)  a 1:1 mixture of enantiomeric epoxides. 
C)  a meso diol. 
D)  a 1:1 mixture of enantiomeric diols. 
E)  hexan-3-ol. 
A)  a meso epoxide. 
B)  a 1:1 mixture of enantiomeric epoxides. 
C)  a meso diol. 
D)  a 1:1 mixture of enantiomeric diols. 
E)  hexan-3-ol.

Question 4

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 5

When hexan-1-ol is treated with conc. H2SO4 at moderate temperatures, ________ is formed via a(n) ________ mechanism.

Accepted Answer

A)  di-n-hexyl ether, SN2 
B)  di-n-hexyl ether, SN1 
C)  di-n-hexyl ether, E2 
D)  di-n-propyl ether, E1 
E)  hex-1-ene, SN1 
A)  di-n-hexyl ether, SN2 
B)  di-n-hexyl ether, SN1 
C)  di-n-hexyl ether, E2 
D)  di-n-propyl ether, E1 
E)  hex-1-ene, SN1

Question 6

Can one prepare di-sec-butyl ether in good yield by heating butan-2-ol in the presence of sulfuric acid? Explain.

Accepted Answer

This would not be an appropriate method

Question 7

Provide the major organic product in the reaction below.

Accepted Answer

The answer of Provide the major organic product in the...

Question 8

Provide the major organic product in the reaction below.

Accepted Answer

The answer of Provide the major organic product in the...

Question 9

Which of the following reactions or series of reactions will lead to formation of trans-2-methoxycyclohexanol?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 10

What complex results when BF3 is dissolved in dimethyl ether?

Accepted Answer

Question 11

Through what mechanism can a 1,2-halohydrin be converted into an epoxide?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E2 
D)  electrophilic addition 
E)  polymerization 
A)  SN1 
B)  SN2 
C)  E2 
D)  electrophilic addition 
E)  polymerization

Question 12

Provide an acceptable name for the compound shown below.
CH3OCH2CH(CH3)2

Accepted Answer

isobutyl methyl ethe

Question 13

Which of the following compounds would undergo autoxidation most readily?

Accepted Answer

A)  dibenzyl ether 
B)  MTBE 
C)  diethyl ether 
D)  isobutyl phenyl ether 
A)  dibenzyl ether 
B)  MTBE 
C)  diethyl ether 
D)  isobutyl phenyl ether

Question 14

Predict the products of the following reaction and give a reasonable mechanism for their formation.

Accepted Answer

The answer of Predict the products of the following reaction...

Question 15

Provide the structure of the fragment in the mass spectrum of dipropyl ether that results from a cleavage.

Accepted Answer

The answer of Provide the structure of the fragment in...

Question 16

Which of the following reactions or series of reactions will lead to the formation of methoxycyclohexane?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 17

What compound is formed when methyloxirane is reacted with ethylmagnesium bromide followed by treatment with aqueous acid?

Accepted Answer

A)  1-pentanol 
B)  2-pentanol 
C)  2-methyl-1-butanol 
D)  2-methyl-2-butanol 
E)  3-methyl-1-butanol 
A)  1-pentanol 
B)  2-pentanol 
C)  2-methyl-1-butanol 
D)  2-methyl-2-butanol 
E)  3-methyl-1-butanol

Question 18

Provide the major organic product of the following.

Accepted Answer

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

Question 19

Show the best method for preparing methoxycyclopentane via the Williamson ether synthesis.

Accepted Answer

The answer of Show the best method for preparing methoxycyclopentane...

Question 20

What is the major difference in the structure of the product formed in a Grignard reaction when an alkyl magnesium halide (Grignard reagent) is reacted with an epoxide rather than an aldehyde or ketone followed by work-up with H3O+?

Accepted Answer

A)  The alkyl group from the Grignard reagent will be bonded to the α-carbon of the alcohol product. 
B)  The alkyl group from the Grignard reagent will be bonded to the β-carbon of the alcohol product. 
C)  The alkyl group from the Grignard reagent will form an ether product rather than an alcohol product. 
D)  Two equivalents of the Grignard will result in the bonding of two alkyl groups to the α-carbon of the alcohol product. 
E)  The epoxide will protonate the Grignard reagent resulting an alkane product. 
A)  The alkyl group from the Grignard reagent will be bonded to the α-carbon of the alcohol product. 
B)  The alkyl group from the Grignard reagent will be bonded to the β-carbon of the alcohol product. 
C)  The alkyl group from the Grignard reagent will form an ether product rather than an alcohol product. 
D)  Two equivalents of the Grignard will result in the bonding of two alkyl groups to the α-carbon of the alcohol product. 
E)  The epoxide will protonate the Grignard reagent resulting an alkane product.

Exam 14: Ethers, Epoxides, and Thioethers

Which of the following reactions is classified as a Williamson ether synthesis?

Di-n-pentyl ether can be converted to 1-bromopentane by treatment with HBr through essentially a(n) ________ mechanism.

When trans-hex-3-ene is treated with PhCO3H, the major organic product is:

Provide the major organic product of the reaction shown below.

When hexan-1-ol is treated with conc. H2SO4 at moderate temperatures, ________ is formed via a(n) ________ mechanism.

Can one prepare di-sec-butyl ether in good yield by heating butan-2-ol in the presence of sulfuric acid? Explain.

Provide the major organic product in the reaction below.

Provide the major organic product in the reaction below.

Which of the following reactions or series of reactions will lead to formation of trans-2-methoxycyclohexanol?

What complex results when BF3 is dissolved in dimethyl ether?

Through what mechanism can a 1,2-halohydrin be converted into an epoxide?

Provide an acceptable name for the compound shown below. CH3OCH2CH(CH3)2

Which of the following compounds would undergo autoxidation most readily?

Predict the products of the following reaction and give a reasonable mechanism for their formation.

Provide the structure of the fragment in the mass spectrum of dipropyl ether that results from a cleavage.

Which of the following reactions or series of reactions will lead to the formation of methoxycyclohexane?

What compound is formed when methyloxirane is reacted with ethylmagnesium bromide followed by treatment with aqueous acid?

Provide the major organic product of the following.

Show the best method for preparing methoxycyclopentane via the Williamson ether synthesis.

What is the major difference in the structure of the product formed in a Grignard reaction when an alkyl magnesium halide (Grignard reagent) is reacted with an epoxide rather than an aldehyde or ketone followed by work-up with H3O+?

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

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

When trans-hex-3-ene is treated with PhCO₃H, the major organic product is:

When hexan-1-ol is treated with conc. H₂SO₄ at moderate temperatures, is formed via a(n) mechanism.

What complex results when BF₃ is dissolved in dimethyl ether?

Provide an acceptable name for the compound shown below. CH₃OCH₂CH(CH₃)₂

What is the major difference in the structure of the product formed in a Grignard reaction when an alkyl magnesium halide (Grignard reagent) is reacted with an epoxide rather than an aldehyde or ketone followed by work-up with H₃O⁺?