Question 1

Identify the sequence of reactions that successfully completes the following transformation.

Accepted Answer

A)  1. BH3 2. H2O2 / NaOH 3. P, I2 
B)  HI / hν 
C)  1. HBr / hν 2. NaI, acetone 
D)  A and C 
E)  all of the above 
A)  1. BH3 2. H2O2 / NaOH 3. P, I2 
B)  HI / hν 
C)  1. HBr / hν 2. NaI, acetone 
D)  A and C 
E)  all of the above

Question 2

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.
(CH3)3CCH2OH + HBr →

Accepted Answer

Question 3

Provide the structure of the major organic product which results when ethyl tosylate is reacted with potassium t-butoxide.

Accepted Answer

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

Question 4

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

Accepted Answer

Question 5

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 6

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 7

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 8

Provide the major organic product of the following.

Accepted Answer

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

Question 9

Provide a detailed, stepwise mechanism for the reaction below.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 10

Which undergoes dehydration using concentrated H2SO4 faster, cyclopentanol or 1-methylcyclopentanol? Explain briefly.

Accepted Answer

1-methylcyclopentano

Question 11

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 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

Provide the major organic product of the following reaction.

Accepted Answer

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

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

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 16

Provide the structure of the major organic product in the reaction below.
PhCH2(OH)CH3

Accepted Answer

Question 17

What class of organic compound is the major product of the acid catalyzed reaction of an alcohol with a carboxylic acid?

Accepted Answer

A)  ether 
B)  ester 
C)  thiol 
D)  nitrile 
E)  sulfonate ester 
A)  ether 
B)  ester 
C)  thiol 
D)  nitrile 
E)  sulfonate ester

Question 18

Nitroglycerine is formed by the reaction of glycerine (propane-1,2,3-triol) and nitric acid. Provide the structure of nitroglycerine.

Accepted Answer

The answer of Nitroglycerine is formed by the reaction of...

Question 19

What series of synthetic steps could be used to prepare (CH3)2CHCHO from (CH3)3CH?

Accepted Answer

1. Br₂, hν

Question 20

Provide the major organic product of the reaction shown.

Accepted Answer

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

Exam 11: Reactions of Alcohols

Identify the sequence of reactions that successfully completes the following transformation.

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation. (CH3)3CCH2OH + HBr →

Provide the structure of the major organic product which results when ethyl tosylate is reacted with potassium t-butoxide.

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

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

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

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

Provide the major organic product of the following.

Provide a detailed, stepwise mechanism for the reaction below.

Which undergoes dehydration using concentrated H2SO4 faster, cyclopentanol or 1-methylcyclopentanol? Explain briefly.

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

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

Provide the major organic product of the following reaction.

Provide the major organic product of the reaction shown.

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

Provide the structure of the major organic product in the reaction below. PhCH2(OH)CH3

What class of organic compound is the major product of the acid catalyzed reaction of an alcohol with a carboxylic acid?

Nitroglycerine is formed by the reaction of glycerine (propane-1,2,3-triol) and nitric acid. Provide the structure of nitroglycerine.

What series of synthetic steps could be used to prepare (CH3)2CHCHO from (CH3)3CH?

Provide the major organic product of the reaction shown.

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

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation. (CH₃)₃CCH₂OH + HBr →

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

Which undergoes dehydration using concentrated H₂SO₄ faster, cyclopentanol or 1-methylcyclopentanol? Explain briefly.

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

Provide the structure of the major organic product in the reaction below. PhCH₂(OH)CH₃

What series of synthetic steps could be used to prepare (CH₃)₂CHCHO from (CH₃)₃CH?