Question 1

What would be the final product?

Accepted Answer

A) CH3CH2CH2NH2 
B) CH3CH2CONH2 
C) CH3CH2CONHCOCH2CH3 
D) CH3CH2CN 
E) CH3CH2COO-NH4+ 
A) CH3CH2CH2NH2 
B) CH3CH2CONH2 
C) CH3CH2CONHCOCH2CH3 
D) CH3CH2CN 
E) CH3CH2COO-NH4+

Question 2

Which compound would be least reactive toward nucleophilic acyl addition-elimination?

Accepted Answer

A) CH3CHO 
B) CH3COCl 
C) (CH3CO)2O 
D) CH3CONH2 
E) CH3CO2CH3 
A) CH3CHO 
B) CH3COCl 
C) (CH3CO)2O 
D) CH3CONH2 
E) CH3CO2CH3

Question 3

Acyl compounds tend to react by acyl substitution mechanisms because they all have a good or reasonably good ___ attached to the carbonyl carbon.

Accepted Answer

The answer of Acyl compounds tend to react by acyl...

Question 4

Which compound would be the strongest acid?

Accepted Answer

A) 4,4-dichlorobutanoic acid 
B) 3,4-dichlorobutanoic acid 
C) 3,3-dichlorobutanoic acid 
D) 2,3-dichlorobutanoic acid 
E) 2,2-dichlorobutanoic acid 
A) 4,4-dichlorobutanoic acid 
B) 3,4-dichlorobutanoic acid 
C) 3,3-dichlorobutanoic acid 
D) 2,3-dichlorobutanoic acid 
E) 2,2-dichlorobutanoic acid

Question 5

Which compound would be most reactive toward nucleophilic acyl addition-elimination?

Accepted Answer

A) CH3COCH3 
B) CH3COCl 
C) (CH3CO)2O 
D) CH3CONH2 
E) CH3CO2CH3 
A) CH3COCH3 
B) CH3COCl 
C) (CH3CO)2O 
D) CH3CONH2 
E) CH3CO2CH3

Question 6

Predict the major organic product of the 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 7

Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?

Accepted Answer

A)    
B)    
C)    
D) All of these choices. 
E) Only two of these choices. 
A)    
B)    
C)    
D) All of these choices. 
E) Only two of these choices.

Question 8

Which of the following would serve as syntheses of (CH3)3CCO2H?

Accepted Answer

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

Question 9

When a gamma-hydroxy acid is treated with dilute acid,cyclization occurs,producing a ___.

Accepted Answer

lactone (c

Question 10

What is the expected product,A,of the following reaction sequence?

Accepted Answer

A) Benzyl formate 
B) Phenylacetic acid 
C) Benzenesulfonic acid 
D) 1-Chloro-1-phenyl acetic acid 
E) Dibenzylketone 
A) Benzyl formate 
B) Phenylacetic acid 
C) Benzenesulfonic acid 
D) 1-Chloro-1-phenyl acetic acid 
E) Dibenzylketone

Question 11

Which of the following reactions would constitute a reasonable synthesis of propyl acetate?

Accepted Answer

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

Question 12

The correct structure for bicyclo[2.2.2]octane-2-carboxylic acid is:

Accepted Answer

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

Question 13

Which of the following acids would be expected to have the smallest value for pKa?

Accepted Answer

A) Acetic acid 
B) Ethanol 
C) Phenol 
D) Acetone 
E) Water 
A) Acetic acid 
B) Ethanol 
C) Phenol 
D) Acetone 
E) Water

Question 14

The product of the following reaction is:

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 compound would be expected to have the highest pKa?

Accepted Answer

A) 4,4-dichlorobutanoic acid 
B) 3,4-dichlorobutanoic acid 
C) 3,3-dichlorobutanoic acid 
D) 2,3-dichlorobutanoic acid 
E) 2,2-dichlorobutanoic acid 
A) 4,4-dichlorobutanoic acid 
B) 3,4-dichlorobutanoic acid 
C) 3,3-dichlorobutanoic acid 
D) 2,3-dichlorobutanoic acid 
E) 2,2-dichlorobutanoic acid

Question 16

Which of the following will not undergo hydrolysis,whether acid or base is present?

Accepted Answer

A) CH3COCl 
B) CH3CONH2 
C) (CH3CO)2O 
D) CH3CO2CH2CH3 
E) CH3COCH2CH2CH3 
A) CH3COCl 
B) CH3CONH2 
C) (CH3CO)2O 
D) CH3CO2CH2CH3 
E) CH3COCH2CH2CH3

Question 17

What would be the final product of this 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 18

Which compound would be most acidic?

Accepted Answer

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

Question 19

Which compound would be the weakest acid?

Accepted Answer

A) water 
B) acetic acid 
C) ethane 
D) acetylene 
E) ethanol 
A) water 
B) acetic acid 
C) ethane 
D) acetylene 
E) ethanol

Question 20

A compound has the molecular formula,C6H12O2.Its IR spectrum shows a strong absorption band near 1740 cm-1; its 1H NMR spectrum consists of two singlets,at $\delta$1.2 and $\delta$ 3.6.The most likely structure for this compound is:

Accepted Answer

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

Exam 17: Carboxylic Acids and Their Derivatives

What would be the final product?

Which compound would be least reactive toward nucleophilic acyl addition-elimination?

Acyl compounds tend to react by acyl substitution mechanisms because they all have a good or reasonably good ___ attached to the carbonyl carbon.

Which compound would be the strongest acid?

Which compound would be most reactive toward nucleophilic acyl addition-elimination?

Predict the major organic product of the reaction sequence,

Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?

Which of the following would serve as syntheses of (CH3)3CCO2H?

When a gamma-hydroxy acid is treated with dilute acid,cyclization occurs,producing a ___.

What is the expected product,A,of the following reaction sequence?

Which of the following reactions would constitute a reasonable synthesis of propyl acetate?

The correct structure for bicyclo[2.2.2]octane-2-carboxylic acid is:

Which of the following acids would be expected to have the smallest value for pKa?

The product of the following reaction is:

Which compound would be expected to have the highest pKa?

Which of the following will not undergo hydrolysis,whether acid or base is present?

What would be the final product of this reaction sequence?

Which compound would be most acidic?

Which compound would be the weakest acid?

A compound has the molecular formula,C6H12O2.Its IR spectrum shows a strong absorption band near 1740 cm-1; its 1H NMR spectrum consists of two singlets,at δ\deltaδ 1.2 and δ\deltaδ 3.6.The most likely structure for this compound is:

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Which of the following would serve as syntheses of (CH₃)₃CCO₂H?

Which of the following acids would be expected to have the smallest value for pK_a?

Which compound would be expected to have the highest pK_a?