Question 1

Rank these carbonyl compounds in order of increasing C=O dipole moment.

Accepted Answer

The answer of Rank these carbonyl compounds in order of...

Question 2

How would you accomplish the following oxidation reaction?

Accepted Answer

The answer of How would you accomplish the following oxidation...

Question 3

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

Accepted Answer

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

Question 4

Which reagents would you use to accomplish the following transformation?

Accepted Answer

A)  LiAlH4, then H3O+ 
B)  NaBH4  in methanol 
C) 1.  CH3MgBr,   
2.  H3O+ 
D) H2,Pd /C 
E)  CH3MgBr  and  H3O+  
A)  LiAlH4, then H3O+ 
B)  NaBH4  in methanol 
C) 1.  CH3MgBr,   
2.  H3O+ 
D) H2,Pd /C 
E)  CH3MgBr  and  H3O+

Question 5

What is the product of the following reaction?

Accepted Answer

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

Question 6

Design a multistep synthesis for the transformation shown here.You may use any organic or inorganic reagents.Show the reagents needed for each step and the product of each step.

Accepted Answer

The answer of Design a multistep synthesis for the transformation...

Question 7

What are the missing reagents in the reaction sequence shown here?

Accepted Answer

A) 1. Na2Cr2O7, H2SO4, H2O
2. NH2OH , trace acid 
B) 1.  LiAlH4
2.  H2O 
3.  NH2OH, trace acid 
C) 1.  NaBH4, MeOH
2.  NH3 , then H3O+ 
D) NH3 , then  H3O+ 
E)  None of these 
A) 1. Na2Cr2O7, H2SO4, H2O
2. NH2OH , trace acid 
B) 1.  LiAlH4
2.  H2O 
3.  NH2OH, trace acid 
C) 1.  NaBH4, MeOH
2.  NH3 , then H3O+ 
D) NH3 , then  H3O+ 
E)  None of these

Question 8

Which of the following compounds will not react with  CrO3/pyridine to give a carbonyl compound?

Accepted Answer

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

Question 9

In the multistep synthesis shown here, what would be the first step?

Accepted Answer

A)  Mg, ether 
B)  CO2 
C)  H3O+ 
D)  KMnO4 
E)    
A)  Mg, ether 
B)  CO2 
C)  H3O+ 
D)  KMnO4 
E)

Question 10

Which of the following compounds cannot be used to form an imine?

Accepted Answer

A)   
B)   
C)   
D)   
E) NH3 
A)   
B)   
C)   
D)   
E) NH3

Question 11

Draw a mechanism to illustrate the removal of the acetal under the conditions shown.Include all necessary lone pairs, curved arrows, and nonzero formal charges.

Accepted Answer

The answer of Draw a mechanism to illustrate the removal...

Question 12

An acyclic compound was treated with trace acid to produce this structure.   Draw the structure of the acyclic compound.

Accepted Answer

The answer of An acyclic compound was treated with trace...

Question 13

Draw a mechanism for the hydration of the compound shown here under acidic conditions. Include all lone pairs, curved arrows, and nonzero formal charges.

Accepted Answer

The answer of Draw a mechanism for the hydration of...

Question 14

Which of the following statements about the biological oxidation of alcohols is false?

Accepted Answer

A)  Alcohol dehydrogenase is an enzyme that binds both ethyl alcohol and nicotinamide adenine dinucleotide NAD+ 
B)   NAD+ is a pyridinium ion and a strong Lewis acid. 
C)  In the reaction catalyzed by alcohol dehydrogenase, ethyl alcohol is reduced and NAD+  is oxidized. 
D)  Alcohol dehydrogenase catalyzes a hydride transfer. 
E)  One of the products of the reaction catalyzed by alcohol dehydrogenase is an aldehyde. 
A)  Alcohol dehydrogenase is an enzyme that binds both ethyl alcohol and nicotinamide adenine dinucleotide NAD+ 
B)   NAD+ is a pyridinium ion and a strong Lewis acid. 
C)  In the reaction catalyzed by alcohol dehydrogenase, ethyl alcohol is reduced and NAD+  is oxidized. 
D)  Alcohol dehydrogenase catalyzes a hydride transfer. 
E)  One of the products of the reaction catalyzed by alcohol dehydrogenase is an aldehyde.

Question 15

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

Accepted Answer

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

Question 16

Which reagent would you use to effect this transformation?

Accepted Answer

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

Question 17

Which carbonyl compounds below has the IUPAC name:  (2 R, 3 S)-2,3 -dibromo-4-methylpentanal?

Accepted Answer

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

Question 18

Use a retrosynthetic analysis to provide five possible precursors to this alcohol. Include the reagents needed to transform each of the precursors to the alcohol.

Accepted Answer

The answer of Use a retrosynthetic analysis to provide five...

Question 19

Which statement about this reaction is correct?

Accepted Answer

A) The products are enantiomers, formed in a racemic mixture. 
B) The products are diastereomers, formed in equal amounts. 
C) The products are enantiomers, formed in unequal amounts. 
D) The products are diastereomers, formed in unequal amounts. 
E) Not enough information is given to predict the products. 
A) The products are enantiomers, formed in a racemic mixture. 
B) The products are diastereomers, formed in equal amounts. 
C) The products are enantiomers, formed in unequal amounts. 
D) The products are diastereomers, formed in unequal amounts. 
E) Not enough information is given to predict the products.

Question 20

Draw a mechanism for the hydration of the compound shown here under basic conditions.Include
all lone pairs, curved arrows, and nonzero formal charges.

Accepted Answer

The answer of Draw a mechanism for the hydration of...

Exam 16: Carbonyl Chemistry 1: Addition Reactions

Rank these carbonyl compounds in order of increasing C=O dipole moment.

How would you accomplish the following oxidation reaction?

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

Which reagents would you use to accomplish the following transformation?

What is the product of the following reaction?

Design a multistep synthesis for the transformation shown here.You may use any organic or inorganic reagents.Show the reagents needed for each step and the product of each step.

What are the missing reagents in the reaction sequence shown here?

Which of the following compounds will not react with CrO3/pyridine to give a carbonyl compound?

In the multistep synthesis shown here, what would be the first step?

Which of the following compounds cannot be used to form an imine?

Draw a mechanism to illustrate the removal of the acetal under the conditions shown.Include all necessary lone pairs, curved arrows, and nonzero formal charges.

An acyclic compound was treated with trace acid to produce this structure. Draw the structure of the acyclic compound.

Draw a mechanism for the hydration of the compound shown here under acidic conditions. Include all lone pairs, curved arrows, and nonzero formal charges.

Which of the following statements about the biological oxidation of alcohols is false?

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

Which reagent would you use to effect this transformation?

Which carbonyl compounds below has the IUPAC name: (2 R, 3 S)-2,3 -dibromo-4-methylpentanal?

Use a retrosynthetic analysis to provide five possible precursors to this alcohol. Include the reagents needed to transform each of the precursors to the alcohol.

Which statement about this reaction is correct?

Draw a mechanism for the hydration of the compound shown here under basic conditions.Include all lone pairs, curved arrows, and nonzero formal charges.

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

Carboxylic Acids

Derivatives of Carboxylic Acids: Acyl Compounds

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

Filters

Which of the following compounds will not react with CrO₃/pyridine to give a carbonyl compound?