Question 1

Draw structures corresponding to each of the following IUPAC names.
-Draw:
cyclopropyl ethyl sulfide

Accepted Answer

The answer of Draw structures corresponding to each of the...

Question 2

The following IR spectrum would most likely be associated with

Accepted Answer

A)  phenol 
B)  aromatic alcohol 
C)  aliphatic alcohol 
D)  ether 
E)  cannot determine from the isolated spectrum 
A)  phenol 
B)  aromatic alcohol 
C)  aliphatic alcohol 
D)  ether 
E)  cannot determine from the isolated spectrum C

Question 3

To answer the following question(s), consider the reaction below.  
-Refer to instructions. The conversion of an alcohol into an alkyl chloride by reaction with SOCl2 is an example of:

Accepted Answer

A)  an E1 process 
B)  an SN1 process 
C)  an E2 process 
D)  an SN2 process 
A)  an E1 process 
B)  an SN1 process 
C)  an E2 process 
D)  an SN2 process D

Question 4

Consider the Grignard reaction below to answer the following question(s).  
-Refer to instructions. The nucleophile in this reaction is indicated by letter _____.

Accepted Answer

A) A 
B) B 
C) C 
A) A 
B) B 
C) C

Question 5

Predict the product of the following reaction.

Accepted Answer

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

Question 6

Which of the following is probably the least useful in IR characterization of a compound?

Accepted Answer

A)  phenol: 3500 cm−1 
B)  alcohol: 3500 cm−1 
C)  phenol: 1500−1600 cm−1 
D)  ether: 1050−1150 cm−1 
E)  all of these are about equally useful 
A)  phenol: 3500 cm−1 
B)  alcohol: 3500 cm−1 
C)  phenol: 1500−1600 cm−1 
D)  ether: 1050−1150 cm−1 
E)  all of these are about equally useful

Question 7

What is the IUPAC name of the following compound?

Accepted Answer

A)  cis-4-methylcyclohexanol 
B)  trans-4-methylcyclohexanol 
C)  cis-4-hydroxy-1-methylcyclohexane 
D)  trans-4-hydroxy-1-methylcyclohexane 
A)  cis-4-methylcyclohexanol 
B)  trans-4-methylcyclohexanol 
C)  cis-4-hydroxy-1-methylcyclohexane 
D)  trans-4-hydroxy-1-methylcyclohexane

Question 8

What is the best way to make the following ether by a Williamson ether synthesis?

Accepted Answer

The answer of What is the best way to make...

Question 9

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 10

What is the IUPAC name of the following compound?

Accepted Answer

A)  cyclohexen-3-ol 
B)  cyclohexen-2-ol 
C)  cyclohex-1-en-3-ol 
D)  cyclohex-2-en-1-ol 
A)  cyclohexen-3-ol 
B)  cyclohexen-2-ol 
C)  cyclohex-1-en-3-ol 
D)  cyclohex-2-en-1-ol

Question 11

Which of the following would not react with either Na2Cr2O7 or pyridinium chlorochromate? A   B   C   D   ​

Accepted Answer

A)  only A 
B)  only C 
C)  only B and D 
D)  A, B, C, and D 
A)  only A 
B)  only C 
C)  only B and D 
D)  A, B, C, and D

Question 12

Predict the major products of the following by drawing the structures of A and B.

Accepted Answer

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

Question 13

Addition of chlorotrimethylsilane to an alcohol

Accepted Answer

A)  results in an SN1 reaction. 
B)  requires acidic reaction conditions. 
C)  is sterically hindered by the three methyl groups. 
D)  results in the formation of an ether. 
E)  produces a more reactive species. 
A)  results in an SN1 reaction. 
B)  requires acidic reaction conditions. 
C)  is sterically hindered by the three methyl groups. 
D)  results in the formation of an ether. 
E)  produces a more reactive species.

Question 14

Consider the Grignard reaction below to answer the following question(s).  
-A useful and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonyl compounds. Show what Grignard reagent and what carbonyl compound you would start with to prepare each alcohol below. List all possibilities.

Accepted Answer

The answer of Consider the Grignard reaction below to answer...

Question 15

Draw structures corresponding to each of the following IUPAC names.
-Draw:
2, 4, 6-trinitrophenol

Accepted Answer

The answer of Draw structures corresponding to each of the...

Question 16

To answer the following question(s), consider the reaction below.  
-Refer to instructions. Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary, secondary, or tertiary.

Accepted Answer

(R)-heptan

Question 17

Which of the following ethers cannot be prepared by a Williamson ether synthesis?

Accepted Answer

A)  tert-butyl phenyl ether 
B)  isopropyl methyl ether 
C)  anisole 
D)  tert-butyl methyl ether 
A)  tert-butyl phenyl ether 
B)  isopropyl methyl ether 
C)  anisole 
D)  tert-butyl methyl ether

Question 18

What is the IUPAC name of the following compound?

Accepted Answer

A)  ethyl isopropyl thiol 
B)  2-methylsulfanylpropane 
C)  ethyl isopropyl disulfide 
D)  ethyl isopropyl sulfide 
A)  ethyl isopropyl thiol 
B)  2-methylsulfanylpropane 
C)  ethyl isopropyl disulfide 
D)  ethyl isopropyl sulfide

Question 19

Provide correct IUPAC names for each of the structures below.
-Name:

Accepted Answer

1-ethoxy-2,2-dimethy

Question 20

How would you synthesize the following class of quinones (ubiquinones) from the corresponding hydroquinones?

Accepted Answer

The answer of How would you synthesize the following class...

Exam 13: Alcohols, Phenols, and Thiols; Ethers and Sulfides

Draw structures corresponding to each of the following IUPAC names. -Draw: cyclopropyl ethyl sulfide

The following IR spectrum would most likely be associated with

To answer the following question(s), consider the reaction below. -Refer to instructions. The conversion of an alcohol into an alkyl chloride by reaction with SOCl2 is an example of:

Consider the Grignard reaction below to answer the following question(s). -Refer to instructions. The nucleophile in this reaction is indicated by letter _____.

Predict the product of the following reaction.

Which of the following is probably the least useful in IR characterization of a compound?

What is the IUPAC name of the following compound?

What is the best way to make the following ether by a Williamson ether synthesis?

What is the major organic product obtained from the following reaction?

What is the IUPAC name of the following compound?

Which of the following would not react with either Na2Cr2O7 or pyridinium chlorochromate? A B C D ​

Predict the major products of the following by drawing the structures of A and B.

Addition of chlorotrimethylsilane to an alcohol

Draw structures corresponding to each of the following IUPAC names. -Draw: 2, 4, 6-trinitrophenol

To answer the following question(s), consider the reaction below. -Refer to instructions. Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary, secondary, or tertiary.

Which of the following ethers cannot be prepared by a Williamson ether synthesis?

What is the IUPAC name of the following compound?

Provide correct IUPAC names for each of the structures below. -Name:

How would you synthesize the following class of quinones (ubiquinones) from the corresponding hydroquinones?

Structure and Bonding

Polar Covalent Bonds; Acids and Bases

Organic Compounds: Alkanes and Their Stereochemistry

Organic Compounds: Cycloalkanes and Their Stereochemistry

Stereochemistry at Tetrahedral Centers

An Overview of Organic Reactions

Alkenes and Alkynes

Reactions of Alkenes and Alkynes

Aromatic Compounds

Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectroscopy

Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectroscopy

Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Organohalides: Nucleophilic Substitutions and Eliminations

Aldehydes and Ketones: Nucleophilic Addition Reactions

Carboxylic Acids and Nitriles

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Alpha-Substitution and Condensation Reactions

Amines and Heterocycles

Biomolecules: Amino Acids, Peptides, and Proteins

Amino Acid Metabolism

Biomolecules: Carbohydrates

Carbohydrate Metabolism

Biomolecules: Lipids and Their Metabolism

Biomolecules: Nucleic Acids and Their Metabolism

Orbitals and Organic Chemistry: Pericyclic Reactionse

Synthetic Polymerse

Filters

To answer the following question(s), consider the reaction below. -Refer to instructions. The conversion of an alcohol into an alkyl chloride by reaction with SOCl₂ is an example of:

Which of the following would not react with either Na₂Cr₂O₇ or pyridinium chlorochromate? A B C D