Question 1

Predict the major organic product of the following reaction:

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 2

What is the correct structure for (R)-5-bromo-2-heptanone?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 3

Which sequence of reactions would be utilized to convert

Accepted Answer

A)  2CH3MgBr,then NH4+ 
B)  HOCH2CH2OH,H3O+;LiAlH4,ether;2CH3MgBr,then NH4+ 
C)  HOCH2CH2OH,H3O+;2CH3MgBr,then NH4+ 
D)  HOCH2CH2OH,H3O+;H2,Pt;CH3OH,NH4+ 
E)  None of the above 
A)  2CH3MgBr,then NH4+ 
B)  HOCH2CH2OH,H3O+;LiAlH4,ether;2CH3MgBr,then NH4+ 
C)  HOCH2CH2OH,H3O+;2CH3MgBr,then NH4+ 
D)  HOCH2CH2OH,H3O+;H2,Pt;CH3OH,NH4+ 
E)  None of the above

Question 4

Select the structure of the major product in the following reaction.

Accepted Answer

A)  Ethylbenzene 
B)  1-Phenylethanol 
C)  Acetophenone 
D)  2-Phenylethanal 
E)  Vinylbenzene 
A)  Ethylbenzene 
B)  1-Phenylethanol 
C)  Acetophenone 
D)  2-Phenylethanal 
E)  Vinylbenzene

Question 5

Which of the following procedures would not yield 3-pentanone as a major product?

Accepted Answer

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

Question 6

Which is the general formula for a thioacetal?

Accepted Answer

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

Question 7

The product,E,of the following reaction sequence,   would be:

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 8

Which Wittig reagent would be used to synthesize

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  Either I or II could be used. 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  Either I or II could be used.

Question 9

The conversion of a trans epoxide to a cis alkene using triphenylphosphine is an example
of a ______________reaction.

Accepted Answer

The answer of The conversion of a trans epoxide to...

Question 10

What is the correct structure for 2,5-dimethylhexanal?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 11

Complete the following reaction sequence,giving structural details of all significant intermediates and the final product.

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 12

Which reagent will not differentiate between 3-butenal and 2-butanone?

Accepted Answer

A)  Br2/CCl4 
B)  Ag2O,OH- 
C)  H2NNHC6H5 
D)  KMnO4,OH- 
E)  None of these 
A)  Br2/CCl4 
B)  Ag2O,OH- 
C)  H2NNHC6H5 
D)  KMnO4,OH- 
E)  None of these

Question 13

The reaction between a phosphorus ylide and an aldehyde or ketone is called the ___________ reaction.

Accepted Answer

The answer of The reaction between a phosphorus ylide and...

Question 14

The product,E,of the following sequence of reactions   would be:

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 15

Propose a structure that fits the following spectroscopic data:
C4H8O
IR: 1737 cm−1
Broadband decoupled 13C NMR: 15.48,41.07,204.86  $\delta$
DEPT Experiments show: signal at 41.07  $\delta$ as CH and signal at 15.48  $\delta$ as CH3

Accepted Answer

The answer of Propose a structure that fits the following...

Question 16

Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1-bromobutane.

Accepted Answer

The answer of Suggest a synthetic strategy for the synthesis...

Question 17

Draw a complete mechanism,using arrow convention to indicate electron movement,
for the following transformation:

Accepted Answer

The answer of Draw a complete mechanism,using arrow convention to...

Question 18

Propose a structure that fits the following spectroscopic data:
C6H12O
IR: 1708 cm−1
Broadband decoupled 13C NMR: 24.61,26.42,44.31,213.81  $\delta$
DEPT Experiments show: signals at 24.61,26.42  $\delta$as CH3

Accepted Answer

The answer of Propose a structure that fits the following...

Question 19

Cis-stilbene (cis-1,2-diphenylethene)can be prepared in high yield from its trans
diastereomer.Propose a reasonable synthesis.

Accepted Answer

The answer of Cis-stilbene (cis-1,2-diphenylethene)can be prepared in high yield...

Question 20

What is the correct IUPAC name for the following compound?

Accepted Answer

A)  2,4-dimethyl-2-pentenone 
B)  2,5-dimethylcyclopenten-3-one 
C)  2,4-dimethylcyclopent-2-enone 
D)  3,5-dimethylcyclopent-2-enone 
E)  2-methyl-5-methylcyclopent-2-enone 
A)  2,4-dimethyl-2-pentenone 
B)  2,5-dimethylcyclopenten-3-one 
C)  2,4-dimethylcyclopent-2-enone 
D)  3,5-dimethylcyclopent-2-enone 
E)  2-methyl-5-methylcyclopent-2-enone

Exam 16: Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Predict the major organic product of the following reaction:

What is the correct structure for (R)-5-bromo-2-heptanone?

Which sequence of reactions would be utilized to convert

Select the structure of the major product in the following reaction.

Which of the following procedures would not yield 3-pentanone as a major product?

Which is the general formula for a thioacetal?

The product,E,of the following reaction sequence, would be:

Which Wittig reagent would be used to synthesize

The conversion of a trans epoxide to a cis alkene using triphenylphosphine is an example of a ______________reaction.

What is the correct structure for 2,5-dimethylhexanal?

Complete the following reaction sequence,giving structural details of all significant intermediates and the final product.

Which reagent will not differentiate between 3-butenal and 2-butanone?

The reaction between a phosphorus ylide and an aldehyde or ketone is called the ___________ reaction.

The product,E,of the following sequence of reactions would be:

Propose a structure that fits the following spectroscopic data: C4H8O IR: 1737 cm−1 Broadband decoupled 13C NMR: 15.48,41.07,204.86 δ\deltaδ DEPT Experiments show: signal at 41.07 δ\deltaδ as CH and signal at 15.48 δ\deltaδ as CH3

Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1-bromobutane.

Draw a complete mechanism,using arrow convention to indicate electron movement, for the following transformation:

Propose a structure that fits the following spectroscopic data: C6H12O IR: 1708 cm−1 Broadband decoupled 13C NMR: 24.61,26.42,44.31,213.81 δ\deltaδ DEPT Experiments show: signals at 24.61,26.42 δ\deltaδ as CH3

Cis-stilbene (cis-1,2-diphenylethene)can be prepared in high yield from its trans diastereomer.Propose a reasonable synthesis.

What is the correct IUPAC name for the following compound?

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Propose a structure that fits the following spectroscopic data: C₄H₈O IR: 1737 cm⁻¹ Broadband decoupled ¹³C NMR: 15.48,41.07,204.86 $\delta$ DEPT Experiments show: signal at 41.07 $\delta$ as CH and signal at 15.48 $\delta$ as CH₃

Propose a structure that fits the following spectroscopic data: C₆H₁₂O IR: 1708 cm⁻¹ Broadband decoupled ¹³C NMR: 24.61,26.42,44.31,213.81 $\delta$ DEPT Experiments show: signals at 24.61,26.42 $\delta$ as CH₃