Question 1

What is the final product of this synthetic sequence?

Accepted Answer

A) 
  
B)  p-BrC6H4CH2C6H5 
C)  C6H5CH2COOH 
D) 
  
E)  C6H5CH2C6H5 
A) 
  
B)  p-BrC6H4CH2C6H5 
C)  C6H5CH2COOH 
D) 
  
E)  C6H5CH2C6H5

Question 2

Which of these gem-diols is expected to be the least stable?

Accepted Answer

A) 
  
B)  CH3CH(OH)2 
C) 
  
D)  C6H5CH(OH)2 
E)  ClCH2CH(OH)2 
A) 
  
B)  CH3CH(OH)2 
C) 
  
D)  C6H5CH(OH)2 
E)  ClCH2CH(OH)2

Question 3

LiAlH4 (LAH)cannot be used to convert carboxylic acids to the corresponding aldehydes because:

Accepted Answer

A)  LAH is not sufficiently reactive. 
B)  RCOOH is converted into RCOOLi. 
C)  RCOOH is reduced to RCH2OH. 
D)  RCOOH is reduced to RCH3. 
E)  RCOOH is converted into R2C=O. 
A)  LAH is not sufficiently reactive. 
B)  RCOOH is converted into RCOOLi. 
C)  RCOOH is reduced to RCH2OH. 
D)  RCOOH is reduced to RCH3. 
E)  RCOOH is converted into R2C=O.

Question 4

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

Accepted Answer

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

Question 5

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 6

Which is the proper name for the structure shown below?

Accepted Answer

A)  7-Bromo-1,4-octynal 
B)  7-Bromo-1,4-octynone 
C)  2-Bromo-5,7-octynal 
D)  7-Bromo-7-methyl-1-heptyne-3-ketone 
E)  7-Bromo-1-octyn-4-one 
A)  7-Bromo-1,4-octynal 
B)  7-Bromo-1,4-octynone 
C)  2-Bromo-5,7-octynal 
D)  7-Bromo-7-methyl-1-heptyne-3-ketone 
E)  7-Bromo-1-octyn-4-one

Question 7

What is the major product of the following reaction sequence?

Accepted Answer

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

Question 8

What is the correct IUPAC name for the following compound?

Accepted Answer

A)  1,1,2-Trimethyl-1,3-hexenone 
B)  1,2-Dimethyl-1,3-hexenone 
C)  2,3-Dimethyl-1,3-heptenone 
D)  2,3-Dimethyl-2-hepten-4-one 
E)  5,6-Dimethyl-5-hepten-4-one 
A)  1,1,2-Trimethyl-1,3-hexenone 
B)  1,2-Dimethyl-1,3-hexenone 
C)  2,3-Dimethyl-1,3-heptenone 
D)  2,3-Dimethyl-2-hepten-4-one 
E)  5,6-Dimethyl-5-hepten-4-one

Question 9

What is the correct structure for 5,5-dimethyl-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 10

Propose a structure that fits the following spectroscopic data:
C4H8O
IR: 1728 cm−1
Broadband decoupled 13C NMR: 13.71,15.69,45.82,202.80  $\delta$
DEPT Experiments show: signal at 13.71  $\delta$ as CH3 and signals at 15.69,45.82  $\delta$ as CH2

Accepted Answer

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

Question 11

Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1717 cm−1
Broadband decoupled 13C NMR: 13.70,17.41,29.78,45.71,208.93  $\delta$
DEPT Experiments show: signals at 13.70,29.78  $\delta$as CH3 and signals at 17.41,45.71  $\delta$as CH2

Accepted Answer

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

Question 12

Acetaldehyde is reacted with excess methanol in acid.The product was isolated and
gave the following 1H NMR spectroscopic data:
1.3  $\delta$ (doublet,3H)
3.4  $\delta$ (singlet,6H)
4.6  $\delta$ (quartet,1H)
Propose a structure consistent with this information.

Accepted Answer

The answer of Acetaldehyde is reacted with excess methanol in...

Question 13

In the total synthesis of the Cecropia juvenile hormone,the following sequence of reactions were used.Draw the intermediate and final product formed.

Accepted Answer

The answer of In the total synthesis of the Cecropia...

Question 14

A compound with formula C5H10O gives two signals only,one a triplet and the other a quartet,in the 1H NMR spectrum.Which of these structures is a possible one for this compound?

Accepted Answer

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

Question 15

What is the major product of the following reaction sequence?

Accepted Answer

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

Question 16

In which of the following reactions is the final product expected to be formed as a racemic mixture?

Accepted Answer

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

Question 17

Which reagent(s)could be used to carry out the following transformation?

Accepted Answer

A)  Zn(Hg),HCl,reflux 
B)  LiAlH4,ether 
C)  HSCH2CH2SH,BF3;then Raney Ni (H2) 
D)  All of the above 
E)  Two of the above 
A)  Zn(Hg),HCl,reflux 
B)  LiAlH4,ether 
C)  HSCH2CH2SH,BF3;then Raney Ni (H2) 
D)  All of the above 
E)  Two of the above

Question 18

Which is the IUPAC name for the structure shown below?

Accepted Answer

A)  (R)-5-Bromo-2-heptanal 
B)  (S)-5-Bromo-2-heptanal 
C)  (R)-5-Bromo-2-heptanone 
D)  (S)-5-Bromo-2-heptanone 
E)  (R)-3-Bromopentyl methyl ketone 
A)  (R)-5-Bromo-2-heptanal 
B)  (S)-5-Bromo-2-heptanal 
C)  (R)-5-Bromo-2-heptanone 
D)  (S)-5-Bromo-2-heptanone 
E)  (R)-3-Bromopentyl methyl ketone

Question 19

What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?

Accepted Answer

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

Question 20

What new compound will eventually be formed when HCl is added to a solution of pentanal in methanol?

Accepted Answer

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

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

What is the final product of this synthetic sequence?

Which of these gem-diols is expected to be the least stable?

LiAlH4 (LAH)cannot be used to convert carboxylic acids to the corresponding aldehydes because:

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

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

Which is the proper name for the structure shown below?

What is the major product of the following reaction sequence?

What is the correct IUPAC name for the following compound?

What is the correct structure for 5,5-dimethyl-2-heptanone?

Propose a structure that fits the following spectroscopic data: C4H8O IR: 1728 cm−1 Broadband decoupled 13C NMR: 13.71,15.69,45.82,202.80 δ\deltaδ DEPT Experiments show: signal at 13.71 δ\deltaδ as CH3 and signals at 15.69,45.82 δ\deltaδ as CH2

Propose a structure that fits the following spectroscopic data: C5H10O IR: 1717 cm−1 Broadband decoupled 13C NMR: 13.70,17.41,29.78,45.71,208.93 δ\deltaδ DEPT Experiments show: signals at 13.70,29.78 δ\deltaδ as CH3 and signals at 17.41,45.71 δ\deltaδ as CH2

Acetaldehyde is reacted with excess methanol in acid.The product was isolated and gave the following 1H NMR spectroscopic data: 1.3 δ\deltaδ (doublet,3H) 3.4 δ\deltaδ (singlet,6H) 4.6 δ\deltaδ (quartet,1H) Propose a structure consistent with this information.

In the total synthesis of the Cecropia juvenile hormone,the following sequence of reactions were used.Draw the intermediate and final product formed.

A compound with formula C5H10O gives two signals only,one a triplet and the other a quartet,in the 1H NMR spectrum.Which of these structures is a possible one for this compound?

What is the major product of the following reaction sequence?

In which of the following reactions is the final product expected to be formed as a racemic mixture?

Which reagent(s)could be used to carry out the following transformation?

Which is the IUPAC name for the structure shown below?

What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?

What new compound will eventually be formed when HCl is added to a solution of pentanal in methanol?

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

LiAlH₄ (LAH)cannot be used to convert carboxylic acids to the corresponding aldehydes because:

Propose a structure that fits the following spectroscopic data: C₄H₈O IR: 1728 cm⁻¹ Broadband decoupled ¹³C NMR: 13.71,15.69,45.82,202.80 $\delta$ DEPT Experiments show: signal at 13.71 $\delta$ as CH₃and signals at 15.69,45.82 $\delta$ as CH₂

Propose a structure that fits the following spectroscopic data: C₅H₁₀O IR: 1717 cm⁻¹ Broadband decoupled ¹³C NMR: 13.70,17.41,29.78,45.71,208.93 $\delta$ DEPT Experiments show: signals at 13.70,29.78 $\delta$ as CH₃and signals at 17.41,45.71 $\delta$ as CH₂

Acetaldehyde is reacted with excess methanol in acid.The product was isolated and gave the following ¹H NMR spectroscopic data: 1.3 $\delta$ (doublet,3H) 3.4 $\delta$ (singlet,6H) 4.6 $\delta$ (quartet,1H) Propose a structure consistent with this information.

A compound with formula C₅H₁₀O gives two signals only,one a triplet and the other a quartet,in the ¹H NMR spectrum.Which of these structures is a possible one for this compound?