Deck 19: More About Amines - Reactions of Heterocylic Compounds

Question 1

What is the systematic name for the following compound?

A)aziridine
B)oxetane
C)oxirane
D)azetidine
E)thiirane

Answer 1

thiirane

Question 2

Provide the major organic product in the reaction below.

Answer 2

Question 3

What results when cis-2-butene is subjected to the following reaction sequence? (1)Cl₂,H₂O,(2)NaOH,(3)H₃O⁺?

A)a meso epoxide
B)a 1:1 mixture of enantiomeric epoxides
C)a meso diol
D)a 1:1 mixture of enantiomeric diols
E)2-butanol

Answer 3

a 1:1 mixture of enantiomeric diols

Question 4

What is the systematic name for the following compound?

A)aziridine
B)oxetane
C)oxirane
D)azetidine
E)thiirane

Question 5

Which of the following is the structure for azetidine?

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

Question 6

Which of the following is a tertiary amine?

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

Question 7

Which of the following is the structure for N-methylpiperidine?

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

Question 8

Draw the structure of piperidine.

Question 9

Provide a structural representation of oxetane.

Question 10

What is the major product of the following reaction?

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

Question 11

The major organic product in the following reaction

A)is an N-acyl pyrrolidine.
B)results from an electrophilic aromatic substitution reaction.
C)results from a nucleophilic aromatic substitution reaction.
D)is a m-disubstituted benzene derivative.
E)both B and D

Question 12

What is the product of the following reaction?

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

Question 13

What is the major product of the following reaction?

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

Question 14

What is the major product of the following reaction?

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

Question 15

What is the stereochemistry of the product in the acid hydrolysis of trans-2,3-epoxybutane?

Question 16

What is the systematic name of the following compound?

A)1-azabicyclo[2.2.2]heptane
B)2-azatricyclo[2.2.2]heptane
C)2-azabicyclo[2.2.2]octane
D)2-azabicyclo[2.2.2]heptane
E)2-azabicyclo[2.2.0]octane

Question 17

What is the major product of the following reaction?

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

Question 18

Provide a structural representation of cis-3-ethyl-1,2-epoxycyclopentane.

Question 19

What is the major product of the following reaction?

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

Question 20

Which of the following is the structure of 1,4-dioxane?

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

Question 21

Provide the major organic product of the reaction shown.

Question 22

Identify oxetane.

A)
B)
C)
D)
E)

Question 23

Name the following compound.

A)1-methyl-N-propyl-1-propananmine
B)N-propyl-2-butanamine
C)3-methyl-4-heptanamine
D)1-ethyl-N-propyl-1-ethanamine
E)1'-methylpropyl-1-propanamine

Question 24

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 25

Draw the structures of piperidine and morpholine and explain their relative basicities.

Question 26

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 27

Provide the major organic products of the reaction shown.

Question 28

Which of the following is a quaternary ammonium ion?

A)
B)
C)
D)
E)

Question 29

What is the product of the following reaction?

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

Question 30

What is the major alkene formed in the following Hofmann elimination?

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

Question 31

Circle the stronger base in the pair below,and briefly explain your choice.

Question 32

What is the major alkene formed in the following Hofmann elimination?

A)CH₃CH CH₂
B)
C)CH₃CH₂CH CH₂
D)
E)

Question 33

Provide the major organic product of the reaction shown.

Question 34

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 35

Draw 2-methylpyrrolidine.

Question 36

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 37

Draw the structure of the aziridinium ion and explain why its pKa is lower than a typical secondary ammonium ion.

Question 38

Provide an acceptable name for the compound shown below.

Question 39

Provide the IUPAC name of the compound shown.

Question 40

Name the following compound.

A)isobutylpropylamine
B)isopentylpropylamine
C)n-butylpropylamine
D)tert-butylpropylamine
E)sec-butylpropylamine

Question 41

Give all organic products for the following reaction.Label the major and minor products.

Question 42

Provide the structure of the major organic product in the reaction below.

Question 43

Provide the major organic product(s)of the reaction below.

Question 44

What is the major alkene produced in the following Cope elimination?

A)CH₂ CH₂
B)CH₃CH CH₂
C)CH₃CH₂N CH₂
D)CH₃CH₂N O
E)CH₃CH₂CH₂N O

Question 45

Give the major product for the following reaction.

A)CH₃CH₂NH₂
B)CH₃CH₂CH₂NH₂
C)CH₃CH₂CH₂NHNH₂
D)CH₃CH₂CH₂N NH
E)CH₃CH₂CH₂CH₂NH₂

Question 46

Provide the major organic product(s)of the reaction below.

Question 47

Which of the following compounds is the most reactive toward electrophilic aromatic substitution?

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

Question 48

What is the major alkene formed in the following reaction?

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

Question 49

Provide the structure of the major organic product in the reaction below.

Question 50

Give all organic products for the following reaction.You may choose more than one answer.

A)
B)
C)
D)
E)

Question 51

Provide the structure of the major organic product in the reaction below.

Question 52

Give the major product for the following reaction.

A)CH₃CH₂NH₂
B)CH₃CH₂CH₂NH₂
C)CH₃CH₂CH₂NHNH₂
D)CH₃CH₂CH₂N NH
E)CH₃CH₂CH₂CH₂NH₂

Question 53

Provide the structure of the major organic product in the reaction below.

Question 54

Provide the major organic product(s)of the reaction below.

Question 55

Give the major product for the following reaction.

Question 56

Give all organic products that result when the compound below is heated.Label the major and minor products.

Question 57

Which of the following aromatic compounds is the most stable?

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

Question 58

Provide the major organic product(s)of the reaction below.

Question 59

Provide the major organic product(s)of the reaction below.

Question 60

Provide the structure of the major organic product in the reaction below.

Question 61

When pyrrole undergoes electrophilic aromatic substitution,at which position does substitution occur?

A)2-position
B)3-position
C)4-position

Question 62

Indicate whether the following molecule is aromatic,antiaromatic,or nonaromatic.

Question 63

Provide the structure of the major organic product in the reaction below.

Question 64

What is the major product of the following reaction?

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

Question 65

Provide the major organic product(s)of the reaction below.

Question 66

Provide the major organic product of the reaction shown.

Question 67

Which of the following compounds is not aromatic?

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

Question 68

Provide the systematic name for the compound below.

Question 69

Which of the following lists the correct order of reactivity of the substrates in electrophilic aromatic substitution reactions?

A)thiophene > pyrrole > furan > benzene
B)benzene > furan > thiophene > pyrrole
C)furan > pyrrole > benzene > thiophene
D)benzene > pyrrole > thiophene > furan
E)pyrrole > furan > thiophene > benzene

Question 70

Which of the following compounds is indole?

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

Question 71

Show how the dipole moments are oriented in pyrrolidine and pyrrole,and explain why they are oriented in opposite directions.

Question 72

Provide the major organic product(s)of the reaction below.

Question 73

When benzofuran is treated with acetic anhydride,the major organic product is

A)2-acetylbenzofuran.
B)3-acetylbenzofuran.
C)4-acetylbenzofuran.
D)5-acetylbenzofuran.
E)7-acetylbenzofuran.

Question 74

What is the major product of the following reaction?

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

Question 75

Circle the stronger base in the pair below,and briefly explain your choice.

Question 76

In the following question choose the best answer.The most basic amine.

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

Question 77

What is the major product of the following reaction?

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

Question 78

Propose a plausible mechanism for the following reaction.

Question 79

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 80

Give the major product for the following reaction.

A)
B)
C)
D)
E)