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

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

Accepted Answer

1) PCC 2) CH₃CH₂MgBr 3) H₃O⁺

Question 3

How could tell a sample of n-butanol from tert-butanol?

Accepted Answer

Use the Lucas test. When adding the reagents, a second phase would form immediately with tert-butanol while it would be much slower with n-butanol.

Question 4

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.
CH3(CH2)6CH2OH + HBr →

Accepted Answer

Question 5

How can the electrophilicity of hydroxyls be increased? Suggest several specific ways.

Accepted Answer

The key is to convert the hydr

Question 6

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 7

Given a sample of (R)-2,3-dimethylhexan-3-ol, which of the following would be the best synthesis of (R)-3-chloro-2,3-dimethylhexane?

Accepted Answer

A)  HCl/ZnCl2 
B)  PCl3 
C)  SOCl2 
D)  1. TsCl/Pyridine
2) NaCl 
E)  none of the above 
A)  HCl/ZnCl2 
B)  PCl3 
C)  SOCl2 
D)  1. TsCl/Pyridine
2) NaCl 
E)  none of the above

Question 8

Which reagent could be used to perform the following reaction?

Accepted Answer

A)  NaOCl/TEMPO 
B)  Swern Oxidation 
C)  DMP (periodane) reagent 
D)  All reagents will work 
A)  NaOCl/TEMPO 
B)  Swern Oxidation 
C)  DMP (periodane) reagent 
D)  All reagents will work

Question 9

When (R)-butan-2-ol is treated with TsCl in pyridine, the product formed is ________.

Accepted Answer

A)  a single enantiomer 
B)  a racemic mixture 
C)  a mixture of diastereomers 
D)  an achial compound 
E)  none of the above 
A)  a single enantiomer 
B)  a racemic mixture 
C)  a mixture of diastereomers 
D)  an achial compound 
E)  none of the above

Question 10

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 11

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 12

What series of synthetic steps could be used to prepare 1-bromopentane from 1-bromopropane?

Accepted Answer

1) Mg, eth

Question 13

What is the best way to make the ether shown below using a Williamson Ether Synthesis reaction?

Accepted Answer

A)  (CH3)3CO- + BrCH3 
B)  (CH3)3CBr + -OCH3 
C)  (CH3)3COH + BrCH3 
D)  (CH3)3CBr + HOCH3 
A)  (CH3)3CO- + BrCH3 
B)  (CH3)3CBr + -OCH3 
C)  (CH3)3COH + BrCH3 
D)  (CH3)3CBr + HOCH3

Question 14

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 15

What type of linkage bonds the individual nucleotides together in DNA?

Accepted Answer

The answer of What type of linkage bonds the individual...

Question 16

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

Accepted Answer

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

Question 17

Name the alcohol that would be used in the Fischer esterification synthesis of ethyl propanoate (CH3CH2O2CCH2CH3).

Accepted Answer

Question 18

Provide the structure of the major organic product that results when 1-octanol is treated with pyridinium chlorochromate.

Accepted Answer

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

Question 19

What compound results when 1-butanol is treated with P/I2?

Accepted Answer

A)  CH3CH2CH2CH2I 
B)  racemic CH3CH2CHICH3 
C)  CH3CH2CH2CH2OP(OH)2 
D)  CH3CH2CH2CH2PI2 
E)  Primary alcohols don't react with P/I2. 
A)  CH3CH2CH2CH2I 
B)  racemic CH3CH2CHICH3 
C)  CH3CH2CH2CH2OP(OH)2 
D)  CH3CH2CH2CH2PI2 
E)  Primary alcohols don't react with P/I2.

Question 20

Dimethyl ether (CH3OCH3) can be prepared by heating methanol in concentrated H2SO4. Provide a detailed, stepwise mechanism for this process.

Accepted Answer

Exam 11: Reactions of Alcohols

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

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

How could tell a sample of n-butanol from tert-butanol?

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation. CH3(CH2)6CH2OH + HBr →

How can the electrophilicity of hydroxyls be increased? Suggest several specific ways.

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

Given a sample of (R)-2,3-dimethylhexan-3-ol, which of the following would be the best synthesis of (R)-3-chloro-2,3-dimethylhexane?

Which reagent could be used to perform the following reaction?

When (R)-butan-2-ol is treated with TsCl in pyridine, the product formed is ________.

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

Provide the major organic product of the following reaction.

What series of synthetic steps could be used to prepare 1-bromopentane from 1-bromopropane?

What is the best way to make the ether shown below using a Williamson Ether Synthesis reaction?

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

What type of linkage bonds the individual nucleotides together in DNA?

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

Name the alcohol that would be used in the Fischer esterification synthesis of ethyl propanoate (CH3CH2O2CCH2CH3).

Provide the structure of the major organic product that results when 1-octanol is treated with pyridinium chlorochromate.

What compound results when 1-butanol is treated with P/I2?

Dimethyl ether (CH3OCH3) can be prepared by heating methanol in concentrated H2SO4. Provide a detailed, stepwise mechanism for this process.

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

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

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation. CH₃(CH₂)₆CH₂OH + HBr →

Name the alcohol that would be used in the Fischer esterification synthesis of ethyl propanoate (CH₃CH₂O₂CCH₂CH₃).

What compound results when 1-butanol is treated with P/I₂?

Dimethyl ether (CH₃OCH₃) can be prepared by heating methanol in concentrated H₂SO₄. Provide a detailed, stepwise mechanism for this process.