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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) None of the above

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

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Arrange the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first. CH3CH2CH2CH2NH2CH3CH2OCH2CH3CH3CH2CH2CH2OH\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { NH } _ { 2 } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OCH } _ { 2 } \mathrm { CH } _ { 3 } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } IIIIII\mathrm { I }\quad\quad\quad\quad\quad\quad\mathrm { II }\quad\quad\quad\quad\quad\quad\mathrm { III }


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

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

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) (S) -methyl-4-hexanamine B) (S) -5-methyl-3-hexanamine C) (R) -2-methyl-4-hexanamine D) (R) -5-methyl-3-hexanamine


A) (S) -methyl-4-hexanamine
B) (S) -5-methyl-3-hexanamine
C) (R) -2-methyl-4-hexanamine
D) (R) -5-methyl-3-hexanamine

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

Correct Answer

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Why is piperidine a stronger base than pyridine?


A) The lone pair of electrons in pyridine is part of the delocalized system.
B) Aromatic compounds are always less basic than non-aromatic compounds.
C) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp hybrid orbital.
D) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp2 hybrid orbital.

E) None of the above
F) All of the above

Correct Answer

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What is the major organic product obtained in the following reaction? What is the major organic product obtained in the following reaction? A) I B) II C) III D) IV


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

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

Correct Answer

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A compound with molecular formula C6H15N exhibits a singlet at 0.9 (1H) , a triplet at 1.10 (3H) , a singlet at 1.15 (9H) , and a quartet at 2.6 (2H) in its 1HNMR spectrum. Its IR spectrum shows one medium absorption band near 3400 cm-1. What is the structure of this compound? A compound with molecular formula C<sub>6</sub>H<sub>15</sub>N exhibits a singlet at <font face= symbol ></font> 0.9 (1H) , a triplet at <font face= symbol ></font> 1.10 (3H) , a singlet at <font face= symbol ></font> 1.15 (9H) , and a quartet at <font face= symbol ></font> 2.6 (2H) in its <sup>1</sup>HNMR spectrum. Its IR spectrum shows one medium absorption band near 3400 cm<sup>-1</sup>. What is the structure of this compound? A) I B) II C) III D) IV


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

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

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) B) and D)
F) C) and D)

Correct Answer

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Why are alkylamines more basic than arylamines?


A) The lone pair electrons are localized in alkylamines and delocalized in arylamines.
B) The lone pair electrons are delocalized in alkylamines and localized in arylamines.
C) The lone pair electrons are less readily available in alkylamines.
D) The lone pair electrons are more readily available in arylamines.

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

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) None of the above
F) C) and D)

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) 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) B) and C)
F) C) and D)

Correct Answer

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Rank the following compounds in order of decreasing basicity, putting the most basic first. Rank the following compounds in order of decreasing basicity, putting the most basic first. A) I > II > III > IV B) I > III > II > IV C) IV > III > I > II D) II > I > III > IV


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

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

Correct Answer

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Why is direct nucleophilic substitution of an alkyl halide with NH3 not a very useful method for preparing primary amines?


A) NH3 is not a nucleophile.
B) Elimination will occur.
C) NH3 is too bulky to act as a nucleophile.
D) Polyalkylation of the amine will result in multiple products.

E) None of the above
F) All of the above

Correct Answer

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Rank the following compounds in order of decreasing basicity, putting the most basic compound first. Rank the following compounds in order of decreasing basicity, putting the most basic compound first. A) II > I > III > IV B) I > II > III > IV C) I > III > II > IV D) IV > II > III > I


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

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

Correct Answer

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Rank the nitrogen atoms in chloroquine, shown below, in order of decreasing basicity, putting the most basic nitrogen atom first. Rank the nitrogen atoms in chloroquine, shown below, in order of decreasing basicity, putting the most basic nitrogen atom first. A) N1 > N2 > N3 B) N2 > N1 > N3 C) N3 > N2 > N1 D) N3 > N1 > N2


A) N1 > N2 > N3
B) N2 > N1 > N3
C) N3 > N2 > N1
D) N3 > N1 > N2

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

Correct Answer

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Select the reagent(s) required for the following transformation. Select the reagent(s) required for the following transformation. A) NaI B) (1) NaNO<sub>2</sub>, HCl; (2) NaI C) (1) NaNO<sub>2</sub>, HCl; (2) I<sub>2</sub> D) I<sub>2</sub>


A) NaI
B) (1) NaNO2, HCl; (2) NaI
C) (1) NaNO2, HCl; (2) I2
D) I2

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

Correct Answer

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