Question 1

In which of the following sequences are the compounds listed in order of increasing acidity?

Accepted Answer

A) NH3 3CH2OH 2O 3COOH 
B) CH3CH2OH 3 2O 3COOH 
C) CH3COOH 3CH2OH 2O 3 2O 3COOH 3CH2OH 3 
E) NH3 2O 3COOH 3CH2OH 
A) NH3 3CH2OH 2O 3COOH 
B) CH3CH2OH 3 2O 3COOH 
C) CH3COOH 3CH2OH 2O 3 2O 3COOH 3CH2OH 3 
E) NH3 2O 3COOH 3CH2OH

Question 2

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

Accepted Answer

A) Acetaldehyde 
B) Acetyl chloride 
C) Acetic anhydride 
D) Acetamide 
E) Methyl acetate 
A) Acetaldehyde 
B) Acetyl chloride 
C) Acetic anhydride 
D) Acetamide 
E) Methyl acetate

Question 3

What would be the final organic product of the following reaction?

Accepted Answer

A) C6H5CO2H 
B) C6H5CH3 
C) C6H5COOCH3 
D) C6H5CHO 
E) C6H5CH2OH 
A) C6H5CO2H 
B) C6H5CH3 
C) C6H5COOCH3 
D) C6H5CHO 
E) C6H5CH2OH

Question 4

Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?

Accepted Answer

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

Question 5

Ethanoic acid (CH3CO2H)is usually called ___,from the Latin for "vinegar."

Accepted Answer

Question 6

A compound has the formula C7H14O2.The 13C and 1H NMR spectral data for this compound are:
13C NMR
Broadband decoupled 13C NMR: 22.2,27.7,32.2,33.8,51.4,174.4 δ
DEPT-90: 27.7 δ
DEPT-135: positive peaks at 22.2,27.7,51.4 δ; negative peaks at 32.2,33.8 δ
1H NMR
0.90 δ,doublet (6H)
1.55 δ,multiplet (3H)
2.30 δ,triplet (2H)
3.67 δ,singlet (3H)
Suggest a structure consistent with this data.

Accepted Answer

Question 7

$\gamma$- and $\delta$-hydroxy acids can be esterified intramolecularly to form compounds known as which of these?

Accepted Answer

A) Anhydrides 
B) Cycloalkenes 
C) Lactones 
D) Lactams 
E) Cyclic ketones 
A) Anhydrides 
B) Cycloalkenes 
C) Lactones 
D) Lactams 
E) Cyclic ketones

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

The product,Z,of the following sequence of reactions is which compound?

Accepted Answer

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

Question 10

Draw the structure for 5-bromo-3-oxohexanoic acid.

Accepted Answer

The answer of Draw the structure for 5-bromo-3-oxohexanoic acid....

Question 11

What is the reactant of the following reaction sequence?

Accepted Answer

A) HCO2CH2C6H5 
B) C6H5CH2COOH 
C) C6H5CH2Cl 
D) C6H5CHClCOOH 
E) O=C(CH2C6H5)2 
A) HCO2CH2C6H5 
B) C6H5CH2COOH 
C) C6H5CH2Cl 
D) C6H5CHClCOOH 
E) O=C(CH2C6H5)2

Question 12

What would be the final 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 13

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

Accepted Answer

A) BrCH2CH2CH2COOH 
B) ClCH2CH2CH2COOH 
C) Cl2CHCH2CH2COOH 
D) ICHBrCH2CH2COOH 
E) BrCCl2CH2CH2COOH 
A) BrCH2CH2CH2COOH 
B) ClCH2CH2CH2COOH 
C) Cl2CHCH2CH2COOH 
D) ICHBrCH2CH2COOH 
E) BrCCl2CH2CH2COOH

Question 14

Which compound would be least 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 15

What would be the final organic product of the following reaction?

Accepted Answer

A) C6H5CH2CH2CO2H 
B) C6H5CH2CH2NH2  
C) C6H5CH2CH(CH3)CN 
D) C6H5CH2CH=NH 
E) C6H5CH2NH2 
A) C6H5CH2CH2CO2H 
B) C6H5CH2CH2NH2  
C) C6H5CH2CH(CH3)CN 
D) C6H5CH2CH=NH 
E) C6H5CH2NH2

Question 16

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 17

A nitrile is prepared from the corresponding primary amide by reaction with which of these?

Accepted Answer

A) HCl 
B) Cl2 
C) P4O10 
D) HOCl 
E) AlCl3 
A) HCl 
B) Cl2 
C) P4O10 
D) HOCl 
E) AlCl3

Question 18

In which of the following are the compounds listed in order of decreasing acidity?

Accepted Answer

A) CH3CO2H > CH3CH2OH > C6H5OH > H2O 
B) C6H5OH > CH3CO2H > H2O > CH3CH2OH 
C) CH3CO2H > H2O > C6H5OH > CH3CH2OH 
D) H2O > CH3CO2H > C6H5OH > CH3CH2OH 
E) None of these choices. 
A) CH3CO2H > CH3CH2OH > C6H5OH > H2O 
B) C6H5OH > CH3CO2H > H2O > CH3CH2OH 
C) CH3CO2H > H2O > C6H5OH > CH3CH2OH 
D) H2O > CH3CO2H > C6H5OH > CH3CH2OH 
E) None of these choices.

Question 19

What is the final product of this sequence of reactions?

Accepted Answer

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

Question 20

Carbonation of a Grignard reagent or the SN2 displacement of an organic halide with cyanide ion followed hydrolysis are both good methods for the conversion of organic halides to carboxylic acids of one more carbon atom.For the following reaction,which of these two procedures would be the process of choice and why?

Accepted Answer

Carbonation of the Grignard is

Exam 17: Carboxylic Acids and Their Derivatives

In which of the following sequences are the compounds listed in order of increasing acidity?

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

What would be the final organic product of the following reaction?

Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?

Ethanoic acid (CH3CO2H)is usually called ___,from the Latin for "vinegar."

γ\gammaγ - and δ\deltaδ -hydroxy acids can be esterified intramolecularly to form compounds known as which of these?

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

The product,Z,of the following sequence of reactions is which compound?

Draw the structure for 5-bromo-3-oxohexanoic acid.

What is the reactant of the following reaction sequence?

What would be the final organic product of the following reaction?

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

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

What would be the final organic product of the following reaction?

Predict the major organic product of the reaction sequence,

A nitrile is prepared from the corresponding primary amide by reaction with which of these?

In which of the following are the compounds listed in order of decreasing acidity?

What is the final product of this sequence of reactions?

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

Ethanoic acid (CH₃CO₂H)is usually called ___,from the Latin for "vinegar."

$\gamma$ - and $\delta$ -hydroxy acids can be esterified intramolecularly to form compounds known as which of these?

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

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