Question 1

Which of the following catalysts is commonly used in industry to dehydrogenate alcohols?

Accepted Answer

A)  CuO 
B)  Na 
C)  NaBH4 
D)  (CH3)2S 
E)  Zn 
A)  CuO 
B)  Na 
C)  NaBH4 
D)  (CH3)2S 
E)  Zn

Question 2

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 3

Complete the following reaction by filling in the necessary reagents.

Accepted Answer

The answer of Complete the following reaction by filling in...

Question 4

Provide the major organic product of the following.

Accepted Answer

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Question 5

Draw the products formed in the Fischer esterification reaction between acetic acid (CH3CO2H) and cyclohexanol.

Accepted Answer

Question 6

Which of the following compounds has carbon in the highest oxidation state?

Accepted Answer

A)  CO2 
B)  CH3C(O)CH3 
C)  CH3CH2OH 
D)  CH3C(OCH2CH3)3 
A)  CO2 
B)  CH3C(O)CH3 
C)  CH3CH2OH 
D)  CH3C(OCH2CH3)3

Question 7

Predict the outcome of the following reaction.

Accepted Answer

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

Question 8

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

Accepted Answer

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Question 9

Which set of reagents will best convert 2,2-dimethylpropan-1-ol (neopentyl alcohol) to 4,4-dimethylpentan-2-ol?

Accepted Answer

A)  1. HCl 2. Mg
3) CH3CHO
4) H3O+ 
B)  1. HCl, ZnCl2 2. Mg
3) CH2O
4) H3O+ 
C)  1. SOCl2 2. Mg
3) CH3CHO
4) H3O+ 
D)  1. HCl, ZnCl2 2. Mg
3) CH3CHO
4) H3O+ 
A)  1. HCl 2. Mg
3) CH3CHO
4) H3O+ 
B)  1. HCl, ZnCl2 2. Mg
3) CH2O
4) H3O+ 
C)  1. SOCl2 2. Mg
3) CH3CHO
4) H3O+ 
D)  1. HCl, ZnCl2 2. Mg
3) CH3CHO
4) H3O+

Question 10

In the chromic acid oxidation of alcohols, the chromium is:

Accepted Answer

A)  oxidized from Cr+3 to Cr+6. 
B)  reduced from Cr+6 to Cr+3. 
C)  oxidized from Cr+6 to Cr+3. 
D)  reduced from Cr+3 to Cr+6. 
E)  none of the above 
A)  oxidized from Cr+3 to Cr+6. 
B)  reduced from Cr+6 to Cr+3. 
C)  oxidized from Cr+6 to Cr+3. 
D)  reduced from Cr+3 to Cr+6. 
E)  none of the above

Question 11

Provide the major organic product of the following.

Accepted Answer

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

Question 12

Which of the following reaction series will result in the formation of a new secondary (2°) alcohol from the beginning alcohol listed at the top?

Accepted Answer

A)  Ethanol 1. Na°
2) CH3CH2I 
B)  t-butyl alcohol 1. K2Cr2O7/acetic acid
2) CH3-MgBr
3) H3O+ 
C)  2-propanol 1. K2Cr2O7/acetic acid
2) CH3-MgBr
3) H3O+ 
D)  n-butanol 1. H2SO4/heat
2) Hg(OAc)2 (aq)
3) NaBH4 
E)  2-methylcycloxexanol 1. H2SO4/heat
2) OsO4/H2O2
3) H2SO4/heat 
A)  Ethanol 1. Na°
2) CH3CH2I 
B)  t-butyl alcohol 1. K2Cr2O7/acetic acid
2) CH3-MgBr
3) H3O+ 
C)  2-propanol 1. K2Cr2O7/acetic acid
2) CH3-MgBr
3) H3O+ 
D)  n-butanol 1. H2SO4/heat
2) Hg(OAc)2 (aq)
3) NaBH4 
E)  2-methylcycloxexanol 1. H2SO4/heat
2) OsO4/H2O2
3) H2SO4/heat

Question 13

Provide the name of the major organic product that results when (R)-2-butyl tosylate is treated with sodium iodide.

Accepted Answer

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

Question 14

Provide the major organic product of the following.

Accepted Answer

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

Question 15

Provide the structure of the major organic product in the reaction below.
(CH3)3CCH2CH2OH   $\rightarrow$

Accepted Answer

(CH<sub>3</sub>)<sub

Question 16

Classify the reaction below as an oxidation, a reduction, or neither. (CH3)2CHCH2OH → (CH3)2CHCHO

Accepted Answer

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

Question 17

What compound is produced when (R)-pentan-2-ol is treated with TsCl followed by NaI?

Accepted Answer

A)  sodium (R)-pent-3-oxide 
B)  sodium (S)-pent-2-oxide 
C)  (R)-2-iodopentane 
D)  (S)-2-iodopentane 
E)  none of the above 
A)  sodium (R)-pent-3-oxide 
B)  sodium (S)-pent-2-oxide 
C)  (R)-2-iodopentane 
D)  (S)-2-iodopentane 
E)  none of the above

Question 18

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 19

Which of the following reagents is the best choice for oxidizing a primary alcohol to an aldehyde?

Accepted Answer

A)  H2CrO4 
B)  pyridinium chlorochromate 
C)  Na2Cr2O7, H2SO4 
D)  KMnO4 
E)  LiAlH4 
A)  H2CrO4 
B)  pyridinium chlorochromate 
C)  Na2Cr2O7, H2SO4 
D)  KMnO4 
E)  LiAlH4

Question 20

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

Accepted Answer

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

Exam 11: Reactions of Alcohols

Which of the following catalysts is commonly used in industry to dehydrogenate alcohols?

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.

Complete the following reaction by filling in the necessary reagents.

Provide the major organic product of the following.

Draw the products formed in the Fischer esterification reaction between acetic acid (CH3CO2H) and cyclohexanol.

Which of the following compounds has carbon in the highest oxidation state?

Predict the outcome of the following reaction.

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

Which set of reagents will best convert 2,2-dimethylpropan-1-ol (neopentyl alcohol) to 4,4-dimethylpentan-2-ol?

In the chromic acid oxidation of alcohols, the chromium is:

Provide the major organic product of the following.

Which of the following reaction series will result in the formation of a new secondary (2°) alcohol from the beginning alcohol listed at the top?

Provide the name of the major organic product that results when (R)-2-butyl tosylate is treated with sodium iodide.

Provide the major organic product of the following.

Provide the structure of the major organic product in the reaction below. (CH3)3CCH2CH2OH →\rightarrow→

Classify the reaction below as an oxidation, a reduction, or neither. (CH3)2CHCH2OH → (CH3)2CHCHO

What compound is produced when (R)-pentan-2-ol is treated with TsCl followed by NaI?

Provide the major organic product of the following reaction.

Which of the following reagents is the best choice for oxidizing a primary alcohol to an aldehyde?

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

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

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. TsCl, pyridine; 2. LiAlH₄.

Draw the products formed in the Fischer esterification reaction between acetic acid (CH₃CO₂H) and cyclohexanol.

Provide the structure of the major organic product in the reaction below. (CH₃)₃CCH₂CH₂OH $Provide the structure of the major organic product in the reaction below. (CH<sub>3</sub>)<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>OH \rightarrow$ $\rightarrow$

Classify the reaction below as an oxidation, a reduction, or neither. (CH₃)₂CHCH₂OH → (CH₃)₂CHCHO