Question 1

What is the IUPAC name of the following compound?

Accepted Answer

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

Question 2

Predict the major product of the following reaction.

Accepted Answer

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

Question 3

Predict the major organic product of the following reaction.

Accepted Answer

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

Question 4

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

Question 5

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

Accepted Answer

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

Question 6

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

Accepted Answer

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

Question 7

Predict the major product of the following reaction.

Accepted Answer

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

Question 8

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 mixture 
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 mixture

Question 9

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

Accepted Answer

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

Question 10

What is the major product of the following reaction?

Accepted Answer

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

Question 11

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 temperature 
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 temperature

Question 12

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

Accepted Answer

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

Question 13

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

Accepted Answer

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

Question 14

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. 
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.

Question 15

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

Question 16

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?

Accepted Answer

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

Question 17

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

Accepted Answer

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

Question 18

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. 
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.

Question 19

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

Accepted Answer

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

Question 20

Predict the major organic product of the following reaction.

Accepted Answer

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

Exam 23: Amines

What is the IUPAC name of the following compound?

Predict the major product of the following reaction.

Predict the major organic product of the following reaction.

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

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

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

Predict the major product of the following reaction.

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

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

What is the major product of the following reaction?

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?

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

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

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

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.

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?

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

Why is piperidine a stronger base than pyridine?

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

Predict the major organic product of the following reaction.

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols,ethers,and Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation,resonance,and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

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

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?