Question 1

What is the correct IUPAC name of the compound below?

Accepted Answer

A)  3-(2-bromopropyl)-6,6-dimethylheptan-2-ol 
B)  5-bromo-3-(3,3-dimethylbutyl)hexan-2-ol 
C)  5-(2-bromopropyl)-2,2-dimethylheptan-6-ol 
D)  7-bromo-5-(1-hydroxyethyl)-2,2-dimethyloctane 
A)  3-(2-bromopropyl)-6,6-dimethylheptan-2-ol 
B)  5-bromo-3-(3,3-dimethylbutyl)hexan-2-ol 
C)  5-(2-bromopropyl)-2,2-dimethylheptan-6-ol 
D)  7-bromo-5-(1-hydroxyethyl)-2,2-dimethyloctane

Question 2

Provide the major organic product(s) of the reaction below.

Accepted Answer

The answer of Provide the major organic product(s) of the...

Question 3

Explain why the synthetic route shown below would be unsuccessful.

Accepted Answer

The tertiary bromide is too hi

Question 4

Provide the major organic product(s) of the reaction below.

Accepted Answer

The answer of Provide the major organic product(s) of the...

Question 5

Provide an acceptable name for the compound below.

Accepted Answer

(R,3E,5Z)-

Question 6

Provide an acceptable name for the compound below.

Accepted Answer

4-bromo-2-

Question 7

Provide the IUPAC name for the following compound.

Accepted Answer

(E)-4,5,5-trimethyl-

Question 8

Which of the following reactions will result in the formation of a secondary alcohol(s) in good yield?

Accepted Answer

A)    
B)    
C)    
D)    
E)  both A and D 
A)    
B)    
C)    
D)    
E)  both A and D

Question 9

Provide the structure of the major organic product in the reaction shown below.

Accepted Answer

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

Question 10

What reagents are needed to complete the following synthesis?

Accepted Answer

1) Br₂ / CH

Question 11

Which is the stronger acid, cyclohexanol or 2-fluorocyclohexan-1-ol?

Accepted Answer

2-fluorocy

Question 12

Provide the reagents necessary to convert (E)-but-2-ene to meso-butane-2,3-diol.

Accepted Answer

The answer of Provide the reagents necessary to convert (E)-but-2-ene...

Question 13

What is the approximate pKa of alcohols, ROH?

Accepted Answer

The answer of What is the approximate pKa of alcohols,...

Question 14

Provide the major organic product(s) of the reaction below.

Accepted Answer

The answer of Provide the major organic product(s) of the...

Question 15

Provide the major organic product(s) of the reaction below.

Accepted Answer

The answer of Provide the major organic product(s) of the...

Question 16

Provide the reagents necessary to accomplish the following transformation.

Accepted Answer

The answer of Provide the reagents necessary to accomplish the...

Question 17

Identify the statement that correctly describes methanol.

Accepted Answer

A)  It is used in alcoholic beverages. 
B)  It can be used as a fuel source but releases less energy than gasoline when combusted. 
C)  It once was used as an anesthetic. 
D)  It is also referred to as rubbing alcohol. 
A)  It is used in alcoholic beverages. 
B)  It can be used as a fuel source but releases less energy than gasoline when combusted. 
C)  It once was used as an anesthetic. 
D)  It is also referred to as rubbing alcohol.

Question 18

Provide the reagents necessary to carry out the conversion shown below.

Accepted Answer

1) Hg(OAc)

Question 19

What two atomic orbitals or hybrid atomic orbitals overlap to form the C-O bond in ethanol?

Accepted Answer

A)  C sp2 + O sp2 
B)  C sp3 + O sp3 
C)  C sp2 + O sp3 
D)  C sp3 + O sp2 
E)  none of the above 
A)  C sp2 + O sp2 
B)  C sp3 + O sp3 
C)  C sp2 + O sp3 
D)  C sp3 + O sp2 
E)  none of the above

Question 20

Rank the following phenols in order of acidity (most acidic = first, least acidic = last).

Accepted Answer

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

Exam 10: Structure and Synthesis of Alcohols

What is the correct IUPAC name of the compound below?

Provide the major organic product(s) of the reaction below.

Explain why the synthetic route shown below would be unsuccessful.

Provide the major organic product(s) of the reaction below.

Provide an acceptable name for the compound below.

Provide an acceptable name for the compound below.

Provide the IUPAC name for the following compound.

Which of the following reactions will result in the formation of a secondary alcohol(s) in good yield?

Provide the structure of the major organic product in the reaction shown below.

What reagents are needed to complete the following synthesis?

Which is the stronger acid, cyclohexanol or 2-fluorocyclohexan-1-ol?

Provide the reagents necessary to convert (E)-but-2-ene to meso-butane-2,3-diol.

What is the approximate pKa of alcohols, ROH?

Provide the major organic product(s) of the reaction below.

Provide the major organic product(s) of the reaction below.

Provide the reagents necessary to accomplish the following transformation.

Identify the statement that correctly describes methanol.

Provide the reagents necessary to carry out the conversion shown below.

What two atomic orbitals or hybrid atomic orbitals overlap to form the C-O bond in ethanol?

Rank the following phenols in order of acidity (most acidic = first, least acidic = last).

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

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

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