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 D

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 B

Question 3

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

Accepted Answer

A) (1)NaNO2,HCl; (2)H2 
B) (1)NaNO2,HCl; (2)H2O 
C) (1)NaNO2,HCl; (2)H3PO4 
D) (1)NaNO2,HCl; (2)H3PO2 
A) (1)NaNO2,HCl; (2)H2 
B) (1)NaNO2,HCl; (2)H2O 
C) (1)NaNO2,HCl; (2)H3PO4 
D) (1)NaNO2,HCl; (2)H3PO2 D

Question 4

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 5

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 6

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

Accepted Answer

A) 90° 
B) 109.5° 
C) 120° 
D) 180° 
A) 90° 
B) 109.5° 
C) 120° 
D) 180°

Question 7

What is the IUPAC name of the following compound?

Accepted Answer

A) N-ethyl-N-methylcyclopentanamine 
B) N-cyclopentyl-N-methylethanamine 
C) N-methyl-N-ethylcyclopentylamine 
D) N-ethyl-N-methylpentanamine 
A) N-ethyl-N-methylcyclopentanamine 
B) N-cyclopentyl-N-methylethanamine 
C) N-methyl-N-ethylcyclopentylamine 
D) N-ethyl-N-methylpentanamine

Question 8

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

Accepted Answer

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

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

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 11

Why is pyrrole much less basic than pyridine?

Accepted Answer

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. 
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.

Question 12

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 13

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 14

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

Accepted Answer

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. 
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.

Question 15

What is the correct assignment of the names of the following aromatic amines?

Accepted Answer

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

Question 16

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 17

Consider the following multistep synthesis.   What is the structure of intermediate C?

Accepted Answer

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

Question 18

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 19

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 20

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

Exam 23: Amines

What is the IUPAC name of the following compound?

Predict the major product of the following reaction.

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

What is the common name of the following compound?

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

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

What is the IUPAC name of the following compound?

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

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

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

Why is pyrrole much less basic than pyridine?

Predict the major product of the following reaction.

What is the major product of the following reaction?

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

What is the correct assignment of the names of the following aromatic amines?

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

Consider the following multistep synthesis. What is the structure of intermediate C?

What is the major product of the following reaction?

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

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?

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

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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?