Question 1

Which of the following reagents is not typically viewed as an oxidizing agent?

Accepted Answer

A)  Cl2 
B)  KMnO4 
C)  O2 
D)  KCl 
E)  H2O2 
A)  Cl2 
B)  KMnO4 
C)  O2 
D)  KCl 
E)  H2O2

Question 2

Provide the major organic product of the following.

Accepted Answer

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

Question 3

Classify the reaction below as an oxidation, a reduction, or neither.
Cis-pent-2-ene → pentane

Accepted Answer

A)  oxidation 
B)  reduction 
C)  neither 
A)  oxidation 
B)  reduction 
C)  neither

Question 4

Through what basic mechanism is 1-methylcyclohexanol converted to 1-bromo-1-methylcyclohexane upon treatment with HBr?

Accepted Answer

A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  radical chain 
A)  SN1 
B)  SN2 
C)  E1 
D)  E2 
E)  radical chain

Question 5

When tert-butanol is heated in sulfuric acid, why is the major product the elimation product and not the ether (substitution product)?

Accepted Answer

The carbocation formed in this

Question 6

Provide the name of the major organic product that results when cyclopentanol is subjected to the following sequence of reactions: 1. NaH; 2. CH3CH2Br.

Accepted Answer

Question 7

Which of the following reactions or series of reactions would reduce 3-methylbutan-2-ol into 2-methylbutane?

Accepted Answer

A)  1. TsCl/pyridine
2) conc. KMnO4 
B)  1. NaOCH3
2). H2SO4/heat 
C)  1. pyridinium chlorochromate
2) ZnCl2/HCl 
D)  1. ZnCl2/HCl
2) t-butoxide/t-butanol 
E)  1. TsCl/pyridine
2) LiAlH4 
A)  1. TsCl/pyridine
2) conc. KMnO4 
B)  1. NaOCH3
2). H2SO4/heat 
C)  1. pyridinium chlorochromate
2) ZnCl2/HCl 
D)  1. ZnCl2/HCl
2) t-butoxide/t-butanol 
E)  1. TsCl/pyridine
2) LiAlH4

Question 8

Provide the name of the major organic product that results when trans-4-methylcyclohexanol is treated with Lucas reagent.

Accepted Answer

a mixture of trans-

Question 9

Provide the major organic product of the following.

Accepted Answer

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

Question 10

Poisonings by methanol and ethylene glycol are relatively common. How are these poisonings treated clinically?

Accepted Answer

The enzyme alcohol dehydrogenase convert

Question 11

Provide the structure of the major organic product in the reaction below.
PhCH2CH(OH)CH3

Accepted Answer

Question 12

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

Accepted Answer

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

Question 13

Which of the following alcohols will give a positive chromic acid test?

Accepted Answer

A)  tert-butanol 
B)  cyclohexanol 
C)  pentan-3-ol 
D)  both A and B 
E)  both B and C 
A)  tert-butanol 
B)  cyclohexanol 
C)  pentan-3-ol 
D)  both A and B 
E)  both B and C

Question 14

Provide the major organic product of the reaction shown.

Accepted Answer

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

Question 15

In the formation of the following ether, which reaction is preferred and why?

Accepted Answer

A)  Reaction B is preferred because the oxidation step works best for primary alcohols. 
B)  Reaction A is preferred over reaction B because the smaller methyl iodide would make a better nucleophilic target. 
C)  Reaction A is preferred because the the formation of the carbocation would be stabilized in the benzylic position. 
D)  Reaction B would be preferred because Iodine is a better leaving group for the SN1 reaction. 
E)  There is no difference in these two reactions - they would give approximately the same yields. 
A)  Reaction B is preferred because the oxidation step works best for primary alcohols. 
B)  Reaction A is preferred over reaction B because the smaller methyl iodide would make a better nucleophilic target. 
C)  Reaction A is preferred because the the formation of the carbocation would be stabilized in the benzylic position. 
D)  Reaction B would be preferred because Iodine is a better leaving group for the SN1 reaction. 
E)  There is no difference in these two reactions - they would give approximately the same yields.

Question 16

What series of synthetic steps could be used to carry out the transformation shown below?

Accepted Answer

1) BH₃ 2) H

Question 17

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

Accepted Answer

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

Question 18

What series of synthetic steps could be used to carry out the transformation shown below?

Accepted Answer

1) PBr₃or HBr 2) Mg,

Question 19

Provide the name of the major organic product that results when cyclopentanol is subjected to the following sequence of reactions: 1. TsCl, pyridine; 2. LiAlH4.

Accepted Answer

Question 20

Octyl acetate (shown below) is an ester that has a strong orange odor. What acid chloride and alcohol would you mix together to make this ester?

Accepted Answer

The answer of Octyl acetate (shown below) is an ester...

Exam 11: Reactions of Alcohols

Which of the following reagents is not typically viewed as an oxidizing agent?

Provide the major organic product of the following.

Classify the reaction below as an oxidation, a reduction, or neither. Cis-pent-2-ene → pentane

Through what basic mechanism is 1-methylcyclohexanol converted to 1-bromo-1-methylcyclohexane upon treatment with HBr?

When tert-butanol is heated in sulfuric acid, why is the major product the elimation product and not the ether (substitution product)?

Provide the name of the major organic product that results when cyclopentanol is subjected to the following sequence of reactions: 1. NaH; 2. CH3CH2Br.

Which of the following reactions or series of reactions would reduce 3-methylbutan-2-ol into 2-methylbutane?

Provide the name of the major organic product that results when trans-4-methylcyclohexanol is treated with Lucas reagent.

Provide the major organic product of the following.

Poisonings by methanol and ethylene glycol are relatively common. How are these poisonings treated clinically?

Provide the structure of the major organic product in the reaction below. PhCH2CH(OH)CH3

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

Which of the following alcohols will give a positive chromic acid test?

Provide the major organic product of the reaction shown.

In the formation of the following ether, which reaction is preferred and why?

What series of synthetic steps could be used to carry out the transformation shown below?

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

What series of synthetic steps could be used to carry out the transformation shown below?

Provide the name of the major organic product that results when cyclopentanol is subjected to the following sequence of reactions: 1. TsCl, pyridine; 2. LiAlH4.

Octyl acetate (shown below) is an ester that has a strong orange odor. What acid chloride and alcohol would you mix together to make this ester?

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

Structure and Synthesis 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

Provide the name of the major organic product that results when cyclopentanol is subjected to the following sequence of reactions: 1. NaH; 2. CH₃CH₂Br.

Provide the structure of the major organic product in the reaction below. PhCH₂CH(OH)CH₃

Provide the name of the major organic product that results when cyclopentanol is subjected to the following sequence of reactions: 1. TsCl, pyridine; 2. LiAlH₄.