Question 1

Which of the following transitions is usually observed in the UV spectra of ketones?

Accepted Answer

A)  n to π* 
B)  n to π 
C)  σ to n 
D)  σ to σ* 
E)  n to σ* 
A)  n to π* 
B)  n to π 
C)  σ to n 
D)  σ to σ* 
E)  n to σ*

Question 2

Provide the structure of 4-oxohexanoic acid.

Accepted Answer

The answer of Provide the structure of 4-oxohexanoic acid....

Question 3

The positively polarized carbon atom of a carbonyl group acts as ________.

Accepted Answer

A)  an electrophile and a Lewis base 
B)  a nucleophile and a Lewis base 
C)  an electrophile and a Lewis acid 
D)  a nucleophile and a Lewis acid 
E)  both a Lewis acid and a Lewis base 
A)  an electrophile and a Lewis base 
B)  a nucleophile and a Lewis base 
C)  an electrophile and a Lewis acid 
D)  a nucleophile and a Lewis acid 
E)  both a Lewis acid and a Lewis base

Question 4

Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and H2NOH.

Accepted Answer

Question 5

The cyclic structure of glucose is shown below. What functional groups are present in this molecule?

Accepted Answer

A)  acetal 
B)  hemiacetal 
C)  oxime 
D)  hydrate 
A)  acetal 
B)  hemiacetal 
C)  oxime 
D)  hydrate

Question 6

Show the acetonide that is formed when 1,2,4,5-tetrahydroxybenzene reacts with 2 equivalents of acetone under acidic conditions.

Accepted Answer

The answer of Show the acetonide that is formed when...

Question 7

The structure of Taxol, a potent chemotherapeutic, is shown below. In the structure, there are ________ ketones and ________ aldehydes.

Accepted Answer

A)  1 ketone; 1 aldehyde 
B)  1 ketone; 0 aldehydes 
C)  6 ketones; 0 aldehydes 
D)  5 ketones; 1 aldehyde 
E)  0 ketones; 0 aldehydes 
A)  1 ketone; 1 aldehyde 
B)  1 ketone; 0 aldehydes 
C)  6 ketones; 0 aldehydes 
D)  5 ketones; 1 aldehyde 
E)  0 ketones; 0 aldehydes

Question 8

Give the structure of the acyclic compound from which the following imine was formed.

Accepted Answer

The answer of Give the structure of the acyclic compound...

Question 9

Oxidation of a 2° alcohol with chromic acid results in the production of ________.

Accepted Answer

A)  an ester 
B)  a ketone 
C)  an aldehyde 
D)  an ether 
E)  none of the above 
A)  an ester 
B)  a ketone 
C)  an aldehyde 
D)  an ether 
E)  none of the above

Question 10

Name the following compound.

Accepted Answer

5,5-difluo

Question 11

Conversion of aldehydes and ketones to imines is an acid-catalyzed process. Explain why this conversion is actually hindered by the presence of too much acid.

Accepted Answer

At very low pH, much

Question 12

Predict the major organic product of the following reaction sequence.

Accepted Answer

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

Question 13

Which of the following reactions will not yield a ketone product?

Accepted Answer

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

Question 14

Acetals will react with ________.

Accepted Answer

A)  H3O+ 
B)  NaOCH3 
C)  PhLi 
D)  CH3CH2MgBr 
E)  NaBH4 
A)  H3O+ 
B)  NaOCH3 
C)  PhLi 
D)  CH3CH2MgBr 
E)  NaBH4

Question 15

Provide the IUPAC name for (CH3)3CCH2CHClCH2CHO.

Accepted Answer

3-chloro-5

Question 16

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 17

Propose a synthesis of 3-heptanone from propanal.

Accepted Answer

1) CH₃CH₂CH₂C

Question 18

Provide the structure of the compound which reacts with a ketone to form its hydrazone derivative.

Accepted Answer

The answer of Provide the structure of the compound which...

Question 19

Provide the major organic product which results when PhCHOHCH3 is treated with PCC.

Accepted Answer

Question 20

What product will result from the reaction shown?

Accepted Answer

A)  imine 
B)  amino acid 
C)  amino alcohol 
D)  hydrazine 
E)  hydroxylamine 
A)  imine 
B)  amino acid 
C)  amino alcohol 
D)  hydrazine 
E)  hydroxylamine

Exam 18: Ketones and Aldehydes

Which of the following transitions is usually observed in the UV spectra of ketones?

Provide the structure of 4-oxohexanoic acid.

The positively polarized carbon atom of a carbonyl group acts as ________.

Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and H2NOH.

The cyclic structure of glucose is shown below. What functional groups are present in this molecule?

Show the acetonide that is formed when 1,2,4,5-tetrahydroxybenzene reacts with 2 equivalents of acetone under acidic conditions.

The structure of Taxol, a potent chemotherapeutic, is shown below. In the structure, there are ________ ketones and ________ aldehydes.

Give the structure of the acyclic compound from which the following imine was formed.

Oxidation of a 2° alcohol with chromic acid results in the production of ________.

Name the following compound.

Conversion of aldehydes and ketones to imines is an acid-catalyzed process. Explain why this conversion is actually hindered by the presence of too much acid.

Predict the major organic product of the following reaction sequence.

Which of the following reactions will not yield a ketone product?

Acetals will react with ________.

Provide the IUPAC name for (CH3)3CCH2CHClCH2CHO.

Provide the major organic product of the reaction shown below.

Propose a synthesis of 3-heptanone from propanal.

Provide the structure of the compound which reacts with a ketone to form its hydrazone derivative.

Provide the major organic product which results when PhCHOHCH3 is treated with PCC.

What product will result from the reaction shown?

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

Reactions 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

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

Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and H₂NOH.

The structure of Taxol, a potent chemotherapeutic, is shown below. In the structure, there are ketones and aldehydes.

Provide the IUPAC name for (CH₃)₃CCH₂CHClCH₂CHO.

Provide the major organic product which results when PhCHOHCH₃ is treated with PCC.