Question 1

Show how the following reaction may be accomplished by filling in the correct reagents.

Accepted Answer

The answer of Show how the following reaction may be...

Question 2

Name the following compound.

Accepted Answer

4,7,7-trimethyl2-oct

Question 3

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

Accepted Answer

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

Question 4

The proton NMR spectrum of an unknown compound contains a triplet at 9.8 ppm. Which of the following could be this unknown?

Accepted Answer

A)  (CH3)3CCHO 
B)  CH3CH2CH2CO2H 
C)  CH3CH2CH2CHO 
D)  CH3CO CH2Ph 
E)  PhCHO 
A)  (CH3)3CCHO 
B)  CH3CH2CH2CO2H 
C)  CH3CH2CH2CHO 
D)  CH3CO CH2Ph 
E)  PhCHO

Question 5

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

Question 6

How might one distinguish an aldehyde from a ketone using IR data alone?

Accepted Answer

The aldehyde has two

Question 7

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 8

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 9

When the carbonyl group of a neutral ketone is protonated,:

Accepted Answer

A)  the resulting species becomes more electrophilic. 
B)  the resulting species is activated toward nucleophilic attack. 
C)  subsequent nucleophilic attack on the resulting species is said to occur under acid-catalyzed conditions. 
D)  the resulting species has a positive charge. 
E)  all of the above 
A)  the resulting species becomes more electrophilic. 
B)  the resulting species is activated toward nucleophilic attack. 
C)  subsequent nucleophilic attack on the resulting species is said to occur under acid-catalyzed conditions. 
D)  the resulting species has a positive charge. 
E)  all of the above

Question 10

Complete the following reaction by filling in the necessary reagents.

Accepted Answer

The answer of Complete the following reaction by filling in...

Question 11

(S)-Carvone is the main component of spearmint oil. What product would result from treating (S)-carvone with DIBAL-H?

Accepted Answer

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

Question 12

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 13

Which of the following compounds is most soluble in water?

Accepted Answer

A)  acetone 
B)  cyclohexanone 
C)  2-butanone 
D)  3-butanone 
E)  benzophenone 
A)  acetone 
B)  cyclohexanone 
C)  2-butanone 
D)  3-butanone 
E)  benzophenone

Question 14

The following compound has been found effective in treating pain and inflammation (J. Med. Chem. 2007, 4222). Which sequence correctly ranks each carbonyl group in order of increasing reactivity toward nucleophilic addition?

Accepted Answer

A)  1 < 2 < 3 
B)  2 < 3 < 1 
C)  3 < 1 < 2 
D)  1 < 3 < 2 
A)  1 < 2 < 3 
B)  2 < 3 < 1 
C)  3 < 1 < 2 
D)  1 < 3 < 2

Question 15

Millad NX8000, shown below, is a clarifying additive for polypropylene ( C & En
News, Sept. 2010, 34). Predict the products of the following reaction.

Accepted Answer

The answer of Millad NX8000, shown below, is a clarifying...

Question 16

Draw two major resonance forms of the cation which results when cyclohexanone's carbonyl group is protonated.

Accepted Answer

The answer of Draw two major resonance forms of the...

Question 17

What reagent can be used to convert 2-methylbutan-1-ol into 2-methylbutanal?

Accepted Answer

A)  LiAlH4 
B)  Na2Cr2O7 
C)  O3 
D)  KMnO4 
E)  PCC 
A)  LiAlH4 
B)  Na2Cr2O7 
C)  O3 
D)  KMnO4 
E)  PCC

Question 18

Propose a synthesis of 4-phenylbutan-2-ol from 3-phenylpropanal.

Accepted Answer

The answer of Propose a synthesis of 4-phenylbutan-2-ol from 3-phenylpropanal....

Question 19

Name the compound generated when ethylbenzene is treated with CO, HCl, AlCl3, and CuCl.

Accepted Answer

Question 20

Which compound will show an intense peak in the mass spectrum at m/z 58?

Accepted Answer

A)  CH3COCH2CH2CH3 
B)  (CH3)2CHCOCH3 
C)  CH3CH2COCH2CH3 
D)  (CH3)3CCHO 
E)  (CH3)3CCOCH3 
A)  CH3COCH2CH2CH3 
B)  (CH3)2CHCOCH3 
C)  CH3CH2COCH2CH3 
D)  (CH3)3CCHO 
E)  (CH3)3CCOCH3

Exam 18: Ketones and Aldehydes

Show how the following reaction may be accomplished by filling in the correct reagents.

Name the following compound.

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

The proton NMR spectrum of an unknown compound contains a triplet at 9.8 ppm. Which of the following could be this unknown?

What product will result from the reaction shown?

How might one distinguish an aldehyde from a ketone using IR data alone?

Provide the major organic product of the reaction shown below.

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

When the carbonyl group of a neutral ketone is protonated,:

Complete the following reaction by filling in the necessary reagents.

(S)-Carvone is the main component of spearmint oil. What product would result from treating (S)-carvone with DIBAL-H?

Provide the major organic product of the reaction shown below.

Which of the following compounds is most soluble in water?

The following compound has been found effective in treating pain and inflammation (J. Med. Chem. 2007, 4222). Which sequence correctly ranks each carbonyl group in order of increasing reactivity toward nucleophilic addition?

Millad NX8000, shown below, is a clarifying additive for polypropylene ( C & En News, Sept. 2010, 34). Predict the products of the following reaction.

Draw two major resonance forms of the cation which results when cyclohexanone's carbonyl group is protonated.

What reagent can be used to convert 2-methylbutan-1-ol into 2-methylbutanal?

Propose a synthesis of 4-phenylbutan-2-ol from 3-phenylpropanal.

Name the compound generated when ethylbenzene is treated with CO, HCl, AlCl3, and CuCl.

Which compound will show an intense peak in the mass spectrum at m/z 58?

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

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

Name the compound generated when ethylbenzene is treated with CO, HCl, AlCl₃, and CuCl.