Question 1

What is the IUPAC name of the following compound?

Accepted Answer

A) N-ethyl-N-methylpentylamine 
B) N-ethyl-N-methyl-1-pentanamine 
C) N-methyl-3-octanamine 
D) N-ethyl-2-heptanamine 
A) N-ethyl-N-methylpentylamine 
B) N-ethyl-N-methyl-1-pentanamine 
C) N-methyl-3-octanamine 
D) N-ethyl-2-heptanamine

Question 2

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 3

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 4

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 5

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 6

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 7

In the preparation of primary amines, how can direct nucleophilic substitution between NH3 and alkyl halide be made more practical than reacting NH3 and the alkyl halide in a 1:1 ratio?

Accepted Answer

A) Use a large excess of NH3. 
B) Use a large excess of alkyl halide. 
C) Use a limited amount of NH3. 
D) Make the alkyl halide sterically hindered. 
A) Use a large excess of NH3. 
B) Use a large excess of alkyl halide. 
C) Use a limited amount of NH3. 
D) Make the alkyl halide sterically hindered.

Question 8

What is the IUPAC name of the following compound?

Accepted Answer

A) (Z)-4-hexen-1-amine 
B) (
E) -4-hexen-1-amine 
C) (
E) -2-hexen-6-amine 
D) (Z)-2-hexen-6-amine 
A) (Z)-4-hexen-1-amine 
B) (
E) -4-hexen-1-amine 
C) (
E) -2-hexen-6-amine 
D) (Z)-2-hexen-6-amine

Question 9

What starting materials are required to synthesize the following azo compound?

Accepted Answer

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

Question 10

The mass spectrum of an amine shows a parent peak with an odd mass for the molecular ion.What does this tell you about the amine?

Accepted Answer

A) The amine is a primary amine. 
B) The amine is a secondary amine. 
C) The amine contains an even number of N atoms. 
D) The amine contains an odd number of N atoms. 
A) The amine is a primary amine. 
B) The amine is a secondary amine. 
C) The amine contains an even number of N atoms. 
D) The amine contains an odd number of N atoms.

Question 11

What is the common name of the following compound?

Accepted Answer

A) dimethylisobutylamine 
B) butyldimethylamine 
C) N,N-dimethylbutanamine 
D) sec-butyldimethylamine 
A) dimethylisobutylamine 
B) butyldimethylamine 
C) N,N-dimethylbutanamine 
D) sec-butyldimethylamine

Question 12

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 13

What is the IUPAC name of the following compound?

Accepted Answer

A) 1-methyl-N-propyl-1-propanamine 
B) 4-methyl-4-heptanamine 
C) 2-propyl-3-hexanamine 
D) N-propyl-2-pentanamine 
A) 1-methyl-N-propyl-1-propanamine 
B) 4-methyl-4-heptanamine 
C) 2-propyl-3-hexanamine 
D) N-propyl-2-pentanamine

Exam 25: Amines

What is the IUPAC name of the following compound?

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

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

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

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

Why is piperidine a stronger base than pyridine?

In the preparation of primary amines, how can direct nucleophilic substitution between NH3 and alkyl halide be made more practical than reacting NH3 and the alkyl halide in a 1:1 ratio?

What is the IUPAC name of the following compound?

What starting materials are required to synthesize the following azo compound?

The mass spectrum of an amine shows a parent peak with an odd mass for the molecular ion.What does this tell you about the amine?

What is the common name of the following compound?

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?

What is the IUPAC name of the following compound?

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

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Filters

In the preparation of primary amines, how can direct nucleophilic substitution between NH₃ and alkyl halide be made more practical than reacting NH₃ and the alkyl halide in a 1:1 ratio?

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?