Question 1

The enzyme, alcohol dehydrogenase, which is produced by the liver, converts ethanol to ________, a normal body metabolite.

Accepted Answer

acetic acid

Question 2

Which reagent would be best suited to induce the following transformation?

Accepted Answer

A)  I2 
B)  HI 
C)  NaI 
D)  P / I2 
A)  I2 
B)  HI 
C)  NaI 
D)  P / I2 D

Question 3

Classify the reaction below as an oxidation, a reduction, or neither. PhCO2H → PhCH2OH

Accepted Answer

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

Question 4

Name the product which results when 1-methylcyclohexanol is treated with PCC.

Accepted Answer

No reaction occurs;

Question 5

Provide the necessary reagents for the following conversion.

Accepted Answer

1) TsCl, p

Question 6

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

Accepted Answer

1. BH₃ 2. H

Question 7

Provide the structure of the major organic product that results when 3-hexanol is treated with sodium dichromate.

Accepted Answer

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

Question 8

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 9

Draw a structure for the expected product of the reaction below.

Accepted Answer

The answer of Draw a structure for the expected product...

Question 10

Provide the name of the major organic product that results when (R)-2-methyl-3-pentanol is heated with conc. H2SO4..

Accepted Answer

Question 11

Which of the following reactions or series of reactions would reduce 3-metylbutan-2-ol into 3-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 12

What series of synthetic steps could be used to prepare 1-methylcyclohexanol from cyclohexene?

Accepted Answer

1. H₂O, H⁺ or BH₃; H₂O₂,

Question 13

Provide the name of the major organic product that results when cyclopentanol is treated with acetyl chloride.

Accepted Answer

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

Question 14

Show the most efficient use of the Williamson ether synthesis to prepare

Accepted Answer

(CH₃)₂CHO^-Na⁺

Question 15

Which energetic material is a nitrate ester?

Accepted Answer

A)  nitroglycerin 
B)  TNT 
C)  RDX 
D)  nitromethane 
A)  nitroglycerin 
B)  TNT 
C)  RDX 
D)  nitromethane

Question 16

Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl2)?

Accepted Answer

A)  (CH3)3COH 
B)  CH3CH2CH2CH2OH 
C)  CH3CH(OH)CH2CH3 
D)  (CH3)2CHCH2OH 
A)  (CH3)3COH 
B)  CH3CH2CH2CH2OH 
C)  CH3CH(OH)CH2CH3 
D)  (CH3)2CHCH2OH

Question 17

Which alcohol reacts most rapidly with the Lucas reagent?

Accepted Answer

A)  benzyl alcohol 
B)  methanol 
C)  2-propanol 
D)  isobutanol 
A)  benzyl alcohol 
B)  methanol 
C)  2-propanol 
D)  isobutanol

Question 18

What series of synthetic steps could be used to prepare PhCH(OH)CH2CH3 from PhCH2OH?

Accepted Answer

1. PCC
2.

Question 19

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 20

Provide the major organic product of the following reaction.

Accepted Answer

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

Exam 11: Reactions of Alcohols

The enzyme, alcohol dehydrogenase, which is produced by the liver, converts ethanol to ________, a normal body metabolite.

Which reagent would be best suited to induce the following transformation?

Classify the reaction below as an oxidation, a reduction, or neither. PhCO2H → PhCH2OH

Name the product which results when 1-methylcyclohexanol is treated with PCC.

Provide the necessary reagents for the following conversion.

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

Provide the structure of the major organic product that results when 3-hexanol is treated with sodium dichromate.

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

Draw a structure for the expected product of the reaction below.

Provide the name of the major organic product that results when (R)-2-methyl-3-pentanol is heated with conc. H2SO4..

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

What series of synthetic steps could be used to prepare 1-methylcyclohexanol from cyclohexene?

Provide the name of the major organic product that results when cyclopentanol is treated with acetyl chloride.

Show the most efficient use of the Williamson ether synthesis to prepare

Which energetic material is a nitrate ester?

Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl2)?

Which alcohol reacts most rapidly with the Lucas reagent?

What series of synthetic steps could be used to prepare PhCH(OH)CH2CH3 from PhCH2OH?

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

Provide the major organic product of the following reaction.

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

Classify the reaction below as an oxidation, a reduction, or neither. PhCO₂H → PhCH₂OH

Provide the name of the major organic product that results when (R)-2-methyl-3-pentanol is heated with conc. H₂SO₄..

Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl₂)?

What series of synthetic steps could be used to prepare PhCH(OH)CH₂CH₃ from PhCH₂OH?