Question 1

Which of the following would undergo racemization in base?

Accepted Answer

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

Question 2

Which of these compounds would exist in an enol form to the greatest extent?

Accepted Answer

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

Question 3

Which of the following hydrogens is the most acidic?

Accepted Answer

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

Question 4

What synthetic strategy would accomplish the following transformation?

Accepted Answer

A)  i)Br2,H3O+;ii)NaOC2H5,C2H5OH,heat 
B)  i)Cl2,FeCl3;ii)NaOC2H5,C2H5OH,heat 
C)  i)HCN;ii)H3O+,heat 
D)  i)Br2,h$\nu$;ii)(CH3)3COK, (CH3)3COH,heat 
E)  None of the above 
A)  i)Br2,H3O+;ii)NaOC2H5,C2H5OH,heat 
B)  i)Cl2,FeCl3;ii)NaOC2H5,C2H5OH,heat 
C)  i)HCN;ii)H3O+,heat 
D)  i)Br2,h$\nu$;ii)(CH3)3COK, (CH3)3COH,heat 
E)  None of the above

Question 5

The conversion of   is accomplished by the use of which oxidizing agent?

Accepted Answer

A)  Ag(NH3)2+ 
B)  O3 
C)  NaOI (I2 in NaOH) 
D) 
  
E)  Cu++ 
A)  Ag(NH3)2+ 
B)  O3 
C)  NaOI (I2 in NaOH) 
D) 
  
E)  Cu++

Question 6

Compounds having two carbonyl groups separated by a carbon atom are called ____________.

Accepted Answer

@#LAT-DLM&-dicarbony

Question 7

When ethylacetoacetate is treated with one equivalent of ethoxide ion followed by one
equivalent of 1,2-dibromoethane compound,X is produced.Treatment of X with a second
equivalent of ethoxide,produces Y.Further treatment of this product to conditions of
saponification,acidification and heating produced a product,Z,that gives the following
spectral data:
1H NMR: 0.88$\delta$multiplet 13CNMR: Broad Band Decoupled: 10.40,21.17,29.84,
208.30$\delta$
1.00$\delta$multiplet DEPT 90: 21.17$\delta$
1.96$\delta$multiplet DEPT 135: positive signals at 21.17,29.84$\delta$
2.24$\delta$ singlet negative signals at 10.40$\delta$
What is a reasonable structure for Z?

Accepted Answer

The answer of When ethylacetoacetate is treated with one equivalent...

Question 8

What would be the major product of the following reaction?

Accepted Answer

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

Question 9

What combination of reagents can be used to make the following substance via an enamine?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these reagents can be used. 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these reagents can be used.

Question 10

Which of the following statements is true of the following enamine?

Accepted Answer

A)  The enamine can be made from cyclopentanone + pyrrolidine. 
B)  It has another resonance structure:
  
C)  It can be acylated at the $\infty$-carbon of the original carbonyl compound. 
D)  It can be alkylated. 
E)  All of the above are true. 
A)  The enamine can be made from cyclopentanone + pyrrolidine. 
B)  It has another resonance structure:
  
C)  It can be acylated at the $\infty$-carbon of the original carbonyl compound. 
D)  It can be alkylated. 
E)  All of the above are true.

Question 11

What is the product,Z,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 12

The kinetic enolate (the less highly substituted double bond)is favored when __________ is used as a base.

Accepted Answer

LDA or lit

Question 13

Which reagent would best serve as the basis for a simple chemical test to distinguish between 2-pentanone and 3-pentanone?

Accepted Answer

A)  NaOI (I2 in NaOH) 
B)  Br2/CCl4 
C)  CrO3/H2SO4 
D)  NaHCO3/H2O 
E)  Ag(NH3)2+ 
A)  NaOI (I2 in NaOH) 
B)  Br2/CCl4 
C)  CrO3/H2SO4 
D)  NaHCO3/H2O 
E)  Ag(NH3)2+

Question 14

Which of the following compounds is the strongest acid?

Accepted Answer

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

Question 15

Which product can be obtained via the following generalized reaction?

Accepted Answer

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

Question 16

What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Accepted Answer

The answer of What is the final product of the...

Question 17

Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity:

Accepted Answer

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

Question 18

What would be 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 19

Which is the most acidic hydrogen in the compound shown?

Accepted Answer

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

Question 20

A compound,X,C9H10O,which reacts with I2/NaOH to give a pale yellow precipitate,gives the following 1H NMR spectrum. Singlet,
 $\delta$2.0
Singlet,
 $\delta$3.0
Multiplet,
 $\delta$7.7
Which is a possible structure for X?

Accepted Answer

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

Exam 18: Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Which of the following would undergo racemization in base?

Which of these compounds would exist in an enol form to the greatest extent?

Which of the following hydrogens is the most acidic?

What synthetic strategy would accomplish the following transformation?

The conversion of is accomplished by the use of which oxidizing agent?

Compounds having two carbonyl groups separated by a carbon atom are called ____________.

What would be the major product of the following reaction?

What combination of reagents can be used to make the following substance via an enamine?

Which of the following statements is true of the following enamine?

What is the product,Z,of the following reaction sequence?

The kinetic enolate (the less highly substituted double bond)is favored when __________ is used as a base.

Which reagent would best serve as the basis for a simple chemical test to distinguish between 2-pentanone and 3-pentanone?

Which of the following compounds is the strongest acid?

Which product can be obtained via the following generalized reaction?

What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity:

What would be the major product of the following reaction sequence?

Which is the most acidic hydrogen in the compound shown?

A compound,X,C9H10O,which reacts with I2/NaOH to give a pale yellow precipitate,gives the following 1H NMR spectrum. Singlet, δ\deltaδ 2.0 Singlet, δ\deltaδ 3.0 Multiplet, δ\deltaδ 7.7 Which is a possible structure for X?

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 I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

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

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