Question 1

Why is piperidine a stronger base than pyridine?

Accepted Answer

A)  The lone pair of electrons in pyridine is part of the delocalized p 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) All of the above
F) B) and D)

Question 2

A compound with molecular formula C6H15N exhibits a singlet at d 0.9 (1H) ,a triplet at d 1.10 (3H) ,a singlet at d1.15 (9H) ,and a quartet at d 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? 6H15N exhibits a singlet at d 0.9 (1H) ,a triplet at d 1.10 (3H) ,a singlet at d1.15 (9H) ,and a quartet at d 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) I B) II C) III D) IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 3

Arrange the following compounds in order of decreasing boiling point,putting the compound with the highest boiling point first.  II > III B) I > III > II C) III > I > II D) III > II > I" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  I > II > III
B)  I > III > II
C)  III > I > II
D)  III > II > IE) All of the above
F) A) and C)

Question 4

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

Accepted Answer

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

Question 5

Predict the major organic product of the following reaction.

Accepted Answer

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

Question 6

Histamine,a vasodilator,is responsible for a wide variety of physiological effects.Rank the three nitrogen atoms in histamine in increasing order of basicity,putting least basic nitrogen atom first.

Accepted Answer

A)  N2 
B)  N1 
C)  N3 
D)  N3 < N2 < N1E) B) and C)
F) A) and C)

Question 7

Select the reagent(s) required for the following transformation. 2,HCl; (2) NaI C) (1) NaNO2,HCl; (2) I2 D) I2" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  NaI
B)  (1) NaNO2,HCl; (2) NaI
C)  (1) NaNO2,HCl; (2) I2
D)  I2E) None of the above
F) A) and B)

Question 8

Although an amine nitrogen atom containing an electron pair and bonded to three different groups is technically a stereogenic center,the chirality of the amine nitrogen is often ignored.Why is that?

Accepted Answer

A)  Because four bonds are needed to define a stereogenic center
B)  Because chirality only exists with the tetrahedral carbon atoms
C)  Because there is usually slow interconversion between the two isomeric forms at room temperature
D)  Because there is usually rapid interconversion between the two isomeric forms at room temperatureE) A) and B)
F) None of the above

Question 9

What is the IUPAC name of the following compound?

Accepted Answer

A)  N-propylhexanamine
B)  N-propylaniline
C)  N-ethylcyclohexylamine
D)  N-propylcyclohexanamineE) A) and B)
F) A) and C)

Question 10

Rank the following compounds in order of decreasing basicity,putting the most basic compound first.  I > III > IV B) I > II > III > IV C) I > III > II > IV D) IV > II > III > I" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  II > I > III > IV
B)  I > II > III > IV
C)  I > III > II > IV
D)  IV > II > III > IE) All of the above
F) A) and D)

Question 11

Rank the nitrogen atoms in chloroquine,shown below,in order of decreasing basicity,putting the most basic nitrogen atom first.  N2 > N3 B) N2 > N1 > N3 C) N3 > N2 > N1 D) N3 > N1 > N2" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  N1 > N2 > N3
B)  N2 > N1 > N3
C)  N3 > N2 > N1
D)  N3 > N1 > N2E) A) and C)
F) C) and D)

Question 12

What is the major organic product obtained in the following reaction?

Accepted Answer

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

Question 13

What is the major product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) B) and C)

Question 14

Arrange the following compounds in order of increasing boiling point,putting the compound with the least boiling point first.

Accepted Answer

A)  I 
B)  II 
C)  I 
D)  II < III < IE) None of the above
F) All of the above

Question 15

Predict the major product of the following reaction.

Accepted Answer

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

Question 16

Predict the major organic product of the following reaction.

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) None of the above

Question 17

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

Accepted Answer

A)  2-Bromo-2-methylbutane
B)  1-Bromo-2-methylbutane
C)  2-Bromo-3-methylbutane
D)  1-Bromo-3-methylbutaneE) None of the above
F) B) and C)

Question 18

Rank the following compounds in order of increasing basicity,putting the least basic compound first.

Accepted Answer

A)  III 
B)  II 
C)  I 
D)  III < I < II < IVE) All of the above
F) A) and B)

Question 19

Why should the chirality of an ammonium salt with four different groups on the nitrogen atom not be ignored?

Accepted Answer

A)  Because there is rapid interconversion between the two isomeric forms at room temperature
B)  Because interconversion cannot occur between the two isomeric forms at room temperature
C)  Because the compound would be a meso compound
D)  Because the compound would be a racemic mixtureE) A) and D)
F) A) and C)

Question 20

Predict the major product of the following reaction.

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) B) and C)

Exam 23: Amines

Although an amine nitrogen atom containing an electron pair and bonded to three different groups is technically a stereogenic center,the chirality of the amine nitrogen is often ignored.Why is that?

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

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Rank the nitrogen atoms in chloroquine,shown below,in order of decreasing basicity,putting the most basic nitrogen atom first.

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A compound with molecular formula C6H15N exhibits a singlet at d 0.9 (1H) ,a triplet at d 1.10 (3H) ,a singlet at d1.15 (9H) ,and a quartet at d 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?

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Rank the following compounds in order of increasing basicity,putting the least basic compound first.

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Arrange the following compounds in order of decreasing boiling point,putting the compound with the highest boiling point first.

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What is the major product of the following reaction?

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What is the IUPAC name of the following compound?

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Rank the following compounds in order of decreasing basicity,putting the most basic compound first.

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Histamine,a vasodilator,is responsible for a wide variety of physiological effects.Rank the three nitrogen atoms in histamine in increasing order of basicity,putting least basic nitrogen atom first.

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Select the reagent(s) required for the following transformation.

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

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Predict the major product of the following reaction.

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Predict the major product of the following reaction.

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Predict the major organic product of the following reaction.

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Why should the chirality of an ammonium salt with four different groups on the nitrogen atom not be ignored?

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Why is piperidine a stronger base than pyridine?

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Predict the major organic product of the following reaction.

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What is the major organic product obtained in the following reaction?

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Arrange the following compounds in order of increasing boiling point,putting the compound with the least boiling point first.

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A compound with molecular formula C₆H₁₅N exhibits a singlet at d 0.9 (1H) ,a triplet at d 1.10 (3H) ,a singlet at d1.15 (9H) ,and a quartet at d 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?

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Why is direct nucleophilic substitution of an alkyl halide with NH₃not a very useful method for preparing primary amines?

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