Question 1

Which of the following is the correct product of the reaction conditions shown?

Accepted Answer

A)   
B)   
C)   
D)   
E)   
A)   
B)   
C)   
D)   
E)   B

Question 2

Provide the structures of two carboxylic acid derivatives from which the compound shown here
could be synthesized, along with the reagents you would use to convert each to the alcohol.

Accepted Answer

The answer of Provide the structures of two carboxylic acid...

Question 3

Which of the following is the product of the reaction conditions shown?

Accepted Answer

A)   
B)   
C)   
D)   
E)   
A)   
B)   
C)   
D)   
E)   B

Question 4

Why is acidic amide hydrolysis irreversible?

Accepted Answer

A) The amine leaving group is protonated, forming an ammonium ion. 
B) The amide carbonyl is protonated. 
C) The amine leaving group is deprotonated, forming an amide ion. 
D) The carboxylic acid formed in the reaction is deprotonated. 
E) The amine formed in the reaction is deprotonated. 
A) The amine leaving group is protonated, forming an ammonium ion. 
B) The amide carbonyl is protonated. 
C) The amine leaving group is deprotonated, forming an amide ion. 
D) The carboxylic acid formed in the reaction is deprotonated. 
E) The amine formed in the reaction is deprotonated.

Question 5

Which of the following is an isolable intermediate in the reaction shown?

Accepted Answer

A)   
B)   
C)   
D)   
E)   
A)   
B)   
C)   
D)   
E)

Question 6

Predict the product of the following reaction.

Accepted Answer

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

Question 7

Which of the following reagents would you use to accomplish this transformation?

Accepted Answer

A)   NaBH4 
B)   LiAlH4 
C)  DIBAL-H 
D)   H2 
E)   H3O+ 
A)   NaBH4 
B)   LiAlH4 
C)  DIBAL-H 
D)   H2 
E)   H3O+

Question 8

Devise a multistep synthesis of the target material from the starting material shown.Show the
reagents needed for each step and the product of each step.Do not draw any mechanisms.

Accepted Answer

The answer of Devise a multistep synthesis of the target...

Question 9

Which has more resonance stabilization, an ester or an acid chloride? Explain your answer.

Accepted Answer

Esters have more resonance stabilization

Question 10

Devise a multistep synthesis of the target molecule from the starting material shown.Show the
reagents needed for each step and the product of each step.Do not show any mechanisms.

Accepted Answer

The answer of Devise a multistep synthesis of the target...

Question 11

Provide the correct IUPAC name for the following compound.

Accepted Answer

3,4-dimeth

Question 12

Predict the product of the reaction conditions shown.

Accepted Answer

The answer of Predict the product of the reaction conditions...

Question 13

Predict the product of the following reaction conditions and draw a mechanism to rationalize its
formation.Include all necessary lone pairs of electrons, curved arrows, and nonzero formal
charges.

Accepted Answer

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

Question 14

Predict the major organic product of the following reaction conditions and draw a mechanism to
rationalize its formation.Include all necessary lone pairs of electrons, curved arrows, and nonzero
formal charges.

Accepted Answer

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

Question 15

Which of the following compounds is the major organic product of the reaction conditions shown?

Accepted Answer

A)   
B)   
C)   
D)   
E)   
A)   
B)   
C)   
D)   
E)

Question 16

For compound A, in acid, it is the hydroxyl oxygen that is protonated to a greater extent than the
carbonyl oxygen.   However, for compound B in acid, it is the carbonyl oxygen that is protonated to a greater extent
than the hydroxyl oxygen.   Explain the difference in these results.

Accepted Answer

In compound A, the hydroxyl oxygen is sp

Question 17

Which reagent would you use to accomplish the following transformation?

Accepted Answer

A)  PLiAlH4 
B)  LiBH4 
C)   NaBH4 
D)  DIBAL-H 
E)  Both  a  and  b 
A)  PLiAlH4 
B)  LiBH4 
C)   NaBH4 
D)  DIBAL-H 
E)  Both  a  and  b

Question 18

What conditions could be used to accomplish the following transformation?

Accepted Answer

A)    
B)    
C)   Br2 , then aqueous NaOH  and heat 
D)   NaBH4 in methanol solvent 
E)  both  b  and  c 
A)    
B)    
C)   Br2 , then aqueous NaOH  and heat 
D)   NaBH4 in methanol solvent 
E)  both  b  and  c

Question 19

Place the following compounds in order of increasing resonance stabilization.

Accepted Answer

A)     
B)     
C)     
D)     
E)     
A)     
B)     
C)     
D)     
E)

Question 20

List the reagents required to convert benzoyl chloride to each product shown.

Accepted Answer

The answer of List the reagents required to convert benzoyl...

Exam 18: Derivatives of Carboxylic Acids: Acyl Compounds

Which of the following is the correct product of the reaction conditions shown?

Provide the structures of two carboxylic acid derivatives from which the compound shown here could be synthesized, along with the reagents you would use to convert each to the alcohol.

Which of the following is the product of the reaction conditions shown?

Why is acidic amide hydrolysis irreversible?

Which of the following is an isolable intermediate in the reaction shown?

Predict the product of the following reaction.

Which of the following reagents would you use to accomplish this transformation?

Devise a multistep synthesis of the target material from the starting material shown.Show the reagents needed for each step and the product of each step.Do not draw any mechanisms.

Which has more resonance stabilization, an ester or an acid chloride? Explain your answer.

Devise a multistep synthesis of the target molecule from the starting material shown.Show the reagents needed for each step and the product of each step.Do not show any mechanisms.

Provide the correct IUPAC name for the following compound.

Predict the product of the reaction conditions shown.

Predict the product of the following reaction conditions and draw a mechanism to rationalize its formation.Include all necessary lone pairs of electrons, curved arrows, and nonzero formal charges.

Predict the major organic product of the following reaction conditions and draw a mechanism to rationalize its formation.Include all necessary lone pairs of electrons, curved arrows, and nonzero formal charges.

Which of the following compounds is the major organic product of the reaction conditions shown?

For compound A, in acid, it is the hydroxyl oxygen that is protonated to a greater extent than the carbonyl oxygen. However, for compound B in acid, it is the carbonyl oxygen that is protonated to a greater extent than the hydroxyl oxygen. Explain the difference in these results.

Which reagent would you use to accomplish the following transformation?

What conditions could be used to accomplish the following transformation?

Place the following compounds in order of increasing resonance stabilization.

List the reagents required to convert benzoyl chloride to each product shown.

Atoms and Molecules; Orbitals and Bonding

Alkanes

Alkenes and Alkynes

Stereochemistry

Rings

Substituted Alkanes: Alkyl Halides, Alcohols, Amines, Ethers,thiols, and Thioethers

Substitution Reactions: the Sn2 and Sn1 Reactions

Elimination Reactions: the E1 and E2 Reactions

Analytical Chemistry: Spectroscopy

Electrophilic Additions to Alkenes

More Additions to Bonds

Radical Reactions

Dienes and the Allyl System: 2p Orbitals in Conjugation

Aromaticity

Substitution Reactions of Aromatic Compounds

Carbonyl Chemistry 1: Addition Reactions

Carboxylic Acids

Carbonyl Chemistry 2: Reactions at the Α Position

Special Topic: Carbohydrates

Special Topic: Bio-Organic Chemistry

Special Topic: Amino Acids and Polyamino Acids Peptides and Proteins

Special Topic: Reactions Controlled by Orbital Symmetry

Special Topic: Intramolecular Reactions and Neighboring Group Participation

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