Question 1

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 2

Which organic reagents would you need to make 2-ethylheptanoic acid from diethyl malonate?

Accepted Answer

A)  Bromoethane,1-bromopentane,sodium ethoxide,and potassium tert-butoxide 
B)  3-Bromooctane and sodium ethoxide 
C)  3-Bromoheptane and sodium ethoxide 
D)  1-Bromopropane,2-bromopentane,sodium ethoxide,and potassium tert-butoxide 
E)  2-Bromoheptane and potassium tert-butoxide 
A)  Bromoethane,1-bromopentane,sodium ethoxide,and potassium tert-butoxide 
B)  3-Bromooctane and sodium ethoxide 
C)  3-Bromoheptane and sodium ethoxide 
D)  1-Bromopropane,2-bromopentane,sodium ethoxide,and potassium tert-butoxide 
E)  2-Bromoheptane and potassium tert-butoxide

Question 3

Which of the following is a keto-enol tautomeric pair?

Accepted Answer

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

Question 4

Explain why acylation of active methylene compounds must be carried out in aprotic solvents,typically using NaH to generate the enolate anion: why can sodium ethoxide/ethanol not be used in these reactions?

Accepted Answer

Acylating agents such as acyl halides an

Question 5

What would be the major 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 6

Alkylation of an enolate anion must be done using either a primary,primary allylic or
primary benzylic species because the substitution follows an ___________mechanistic
pathway.

Accepted Answer

The answer of Alkylation of an enolate anion must be...

Question 7

Malonic ester (diethyl malonate)is treated successively with sodium ethoxide (1 eq. ),1-bromopentane,potassium tert-butoxide,iodomethane,hot aqueous NaOH,HCl,and heat.What is the final product?

Accepted Answer

A)  2-Methylheptanoic acid 
B)  3-Methylhexanoic acid 
C)  3-Methylpentanoic acid 
D)  2-Methylpentanoic acid 
E)  Ethyl 2-methylheptanoate 
A)  2-Methylheptanoic acid 
B)  3-Methylhexanoic acid 
C)  3-Methylpentanoic acid 
D)  2-Methylpentanoic acid 
E)  Ethyl 2-methylheptanoate

Question 8

Predict the 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 9

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

Accepted Answer

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

Question 10

Simple enols are less stable than the tautomeric keto forms because:

Accepted Answer

A)  severe angle strain exists in the enol forms. 
B)  fewer atoms are coplanar in the keto form. 
C)  the enol cannot be chiral. 
D)  the C-C  $\pi$ bond is weaker than the C-O  $\pi$ bond. 
E)  Actually,simple enols are the more stable. 
A)  severe angle strain exists in the enol forms. 
B)  fewer atoms are coplanar in the keto form. 
C)  the enol cannot be chiral. 
D)  the C-C  $\pi$ bond is weaker than the C-O  $\pi$ bond. 
E)  Actually,simple enols are the more stable.

Question 11

Which base is employed in the alkylation of ethyl pentanoate with methyl iodide?

Accepted Answer

A)  Sodium methoxide 
B)  Sodium ethoxide 
C)  Sodium hydride 
D)  Potassium tert-butoxide 
E)  Sodium amide 
A)  Sodium methoxide 
B)  Sodium ethoxide 
C)  Sodium hydride 
D)  Potassium tert-butoxide 
E)  Sodium amide

Question 12

Which of these amines is/are used with aldehydes and ketones to form enamines?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  Both I and II 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  Both I and II

Question 13

The $\alpha$-hydrogens on carbonyl carbons are unusually acidic (pKa 19-20)because: _____________.

Accepted Answer

the corresponding an

Question 14

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 15

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 16

Which of the following represent tautomers?

Accepted Answer

A) 
  
B) 
  
C) 
  
D)  All of these 
E)  None of these 
A) 
  
B) 
  
C) 
  
D)  All of these 
E)  None of these

Question 17

What would be the major 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 18

What would be the major product of the following reaction?

Accepted Answer

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

Question 19

Compounds with two electron-withdrawing groups attached to the same carbon atom are known as ____________ or _____________.

Accepted Answer

active hydrogen comp

Question 20

Which of the following is a keto-enol tautomeric pair?

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 is the most acidic hydrogen in the compound shown?

Which organic reagents would you need to make 2-ethylheptanoic acid from diethyl malonate?

Which of the following is a keto-enol tautomeric pair?

Explain why acylation of active methylene compounds must be carried out in aprotic solvents,typically using NaH to generate the enolate anion: why can sodium ethoxide/ethanol not be used in these reactions?

What would be the major product of the following reaction?

Alkylation of an enolate anion must be done using either a primary,primary allylic or primary benzylic species because the substitution follows an ___________mechanistic pathway.

Malonic ester (diethyl malonate)is treated successively with sodium ethoxide (1 eq. ),1-bromopentane,potassium tert-butoxide,iodomethane,hot aqueous NaOH,HCl,and heat.What is the final product?

Predict the product of the following reaction sequence.

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

Simple enols are less stable than the tautomeric keto forms because:

Which base is employed in the alkylation of ethyl pentanoate with methyl iodide?

Which of these amines is/are used with aldehydes and ketones to form enamines?

The α\alphaα -hydrogens on carbonyl carbons are unusually acidic (pKa 19-20)because: _____________.

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

Which is the most acidic hydrogen in the compound shown?

Which of the following represent tautomers?

What would be the major product of the following reaction?

What would be the major product of the following reaction?

Compounds with two electron-withdrawing groups attached to the same carbon atom are known as ____________ or _____________.

Which of the following is a keto-enol tautomeric pair?

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

Filters

The $\alpha$ -hydrogens on carbonyl carbons are unusually acidic (pK_a 19-20)because: _____________.

Compounds with two electron-withdrawing groups attached to the same carbon atom are known as or _.