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Rank the following compounds in order of increasing basicity, putting the least basic first. Rank the following compounds in order of increasing basicity, putting the least basic first. A) II < III < IV < I B) I < II < III < IV C) IV < III < II < I D) II < I < III < IV


A) II < III < IV < I
B) I < II < III < IV
C) IV < III < II < I
D) II < I < III < IV

E) C) and D)
F) All of the above

Correct Answer

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Predict the major organic product of the following reaction. Predict the major organic product of the following reaction. A) I B) II C) III D) IV


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

E) A) and C)
F) B) and C)

Correct Answer

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Why is pyrrole much less basic than pyridine?


A) The lone pair of electrons in pyrrole is located on an sp2 orbital.
B) The lone pair of electrons in pyrrole is part of the aromatic p system.
C) The lone pair of electrons in pyrrole is not part of the aromatic p system.
D) The pKa of the conjugate acid of pyrrole is much greater than the conjugate acid of pyridine.

E) All of the above
F) A) and B)

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B

Predict the product(s) of the following reaction. Predict the product(s) of the following reaction. A) I B) II C) III D) None of the choices


A) I
B) II
C) III
D) None of the choices

E) B) and C)
F) A) and B)

Correct Answer

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What is the correct assignment of the names of the following aromatic amines? What is the correct assignment of the names of the following aromatic amines? A) I = pyrrolidine; II = pyrimidine; III = aniline. B) I = pyrrole; II = pyrimidine; III = anisole. C) I = pyrrolidine; II = pyridine; III =aniline. D) I = pyrrole; II = pyridine; III = aniline.


A) I = pyrrolidine; II = pyrimidine; III = aniline.
B) I = pyrrole; II = pyrimidine; III = anisole.
C) I = pyrrolidine; II = pyridine; III =aniline.
D) I = pyrrole; II = pyridine; III = aniline.

E) A) and B)
F) B) and C)

Correct Answer

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Which of the following amines are classified as tertiary (3°) amines? Which of the following amines are classified as tertiary (3°) amines? A) I B) II C) III D) IV


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

E) A) and B)
F) None of the above

Correct Answer

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B

What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) 3-methyl-1-hexanamine B) 4-methyl-1-hexylamine C) 4-methyl-1-hexanamine D) 3-methyl-6-hexylamine


A) 3-methyl-1-hexanamine
B) 4-methyl-1-hexylamine
C) 4-methyl-1-hexanamine
D) 3-methyl-6-hexylamine

E) A) and B)
F) A) and C)

Correct Answer

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Predict the major organic product of the following reaction. Predict the major organic product of the following reaction. A) I B) II C) III D) IV


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

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

Correct Answer

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What is the common name of the following compound? What is the common name of the following compound? A) isopropylamine B) sec-butylamine C) isobutylamine D) tert-butylamine


A) isopropylamine
B) sec-butylamine
C) isobutylamine
D) tert-butylamine

E) A) and D)
F) B) and D)

Correct Answer

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Why is the N-H bond of an imide especially acidic?


A) The conjugate base is stabilized by electron-donating inductive effect.
B) The conjugate base is stabilized by resonance.
C) The conjugate acid is stabilized by resonance.
D) The conjugate base is stabilized by intramolecular hydrogen bonding.

E) All of the above
F) B) and C)

Correct Answer

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) N-propylhexanamine B) N-propylaniline C) N-ethylcyclohexylamine D) N-propylcyclohexanamine


A) N-propylhexanamine
B) N-propylaniline
C) N-ethylcyclohexylamine
D) N-propylcyclohexanamine

E) A) and B)
F) None of the above

Correct Answer

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D

What is the name given to naturally occurring amines derived from plant sources?


A) Enamines
B) Imines
C) Alkaloids
D) Alkamines

E) A) and D)
F) None of the above

Correct Answer

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Predict the major organic product of the following reaction. Predict the major organic product of the following reaction. A) I B) II C) III D) IV


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

E) A) and B)
F) B) and C)

Correct Answer

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Predict the major product of the following reaction. Predict the major product of the following reaction. A) I B) II C) III D) IV


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

E) B) and C)
F) A) and B)

Correct Answer

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Which of the following alkyl halides cannot be used to prepare primary amines by the Gabriel synthesis?


A) 2-Bromo-2-methylbutane
B) 1-Bromo-2-methylbutane
C) 2-Bromo-3-methylbutane
D) 1-Bromo-3-methylbutane

E) A) and D)
F) A) and C)

Correct Answer

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Predict the major product of the following reaction. Predict the major product of the following reaction. A) I B) II C) III D) IV


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

E) All of the above
F) B) and C)

Correct Answer

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Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH3) ?


A) Because of the electron-withdrawing inductive effect of the alkyl groups
B) Because of the steric hindrance of the alkyl groups
C) Because of the resonance delocalization of the alkyl groups
D) Because of electron-donating inductive effect of the alkyl groups

E) A) and D)
F) A) and B)

Correct Answer

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Arrange the following amines in order of decreasing water solubility, putting the most soluble amine first. Arrange the following amines in order of decreasing water solubility, putting the most soluble amine first. A) I > II > III B) II > I > III C) III > I > II D) II > III > I


A) I > II > III
B) II > I > III
C) III > I > II
D) II > III > I

E) All of the above
F) A) and B)

Correct Answer

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What is the approximate bond angle of the substituents around a nitrogen atom in amines?


A) 90°
B) 109.5°
C) 120°
D) 180°

E) A) and C)
F) None of the above

Correct Answer

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Which of the following amines are classified as primary (1°) amines? Which of the following amines are classified as primary (1°) amines? A) I B) II C) III D) I and II


A) I
B) II
C) III
D) I and II

E) A) and B)
F) A) and C)

Correct Answer

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