Deck 12: Amines

Question 1

Instructions: Based on the following structures, name the compound.
Name:

Answer 1

p-methoxyaniline or 4-methoxyaniline

Question 2

Instructions: Draw structures corresponding to each of the IUPAC names given in the following question(s).
Draw:
diisopropylamine

Answer 2

Question 3

Circle any of the following that would be classified as a heterocyclic amine.

Answer 3

Question 4

Instructions: Draw structures corresponding to each of the IUPAC names given in the following question(s).
Draw:
hexane-1,6-diamine

Question 5

Instructions: Classify each of the nitrogen atoms in the compound shown below as primary, secondary, tertiary, or quaternary.
Classify:

Question 6

Rank the following compounds in order of increasing basicity. Label the least basic compound "1" and the most basic compound "4". Place the number corresponding to the compound's rank in the blank below the compound.

Question 7

In the following series of compounds, which is the most basic and the least basic? Explain your choices.

Question 8

Instructions: Consider the reaction below to answer the following question(s).
Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H₂/Ni.
Refer to instructions. Although the yield of methamphetamine is good, some unreacted phenyl-2-propanone remains after the reaction is complete. Describe how methamphetamine can be separated from phenyl-2-propanone.

Question 9

Instructions: Classify each of the nitrogen atoms in the compound shown below as primary, secondary, tertiary, or quaternary.
Classify:

Question 10

Instructions: Give the major organic product(s) of each of the following reaction or sequence of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 11

Instructions: Give the major organic product(s) of each of the following reaction or sequence of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 12

Instructions: Based on the following structures, name the compound.
Name:

Question 13

Instructions: Draw structures corresponding to each of the IUPAC names given in the following question(s).
Draw:
N,N-dimethylcyclopentylamine

Question 14

Instructions: Consider the reaction below to answer the following question(s).
Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H₂/Ni.
Refer to instructions. The synthesis of methamphetamine by reaction of 2-phenyl-2 propanone with methylamine in the presence of H₂/Ni is referred to as:

A) reductive nitrogenation
B) reactive nitrogenation
C) reductive amination
D) reactive amination

Question 15

Instructions: Classify each of the nitrogen atoms in the compound shown below as primary, secondary, tertiary, or quaternary.
Classify:

Question 16

Instructions: Based on the following structures, name the compound.
Name:

Question 17

Instructions: Classify each of the nitrogen atoms in the compound shown below as primary, secondary, tertiary, or quaternary.
Classify:

Question 18

Instructions: Based on the following structures, name the compound.
Name:

Question 19

Instructions: Consider the reaction below to answer the following question(s).
Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H₂/Ni.
Refer to instructions. Intermediate A is an example of:

A) an imine
B) an enamine
C) an iminium ion
D) an imide

Question 20

Instructions: Consider the reaction below to answer the following question(s).
Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H₂/Ni.
Refer to instructions. Identify the nucleophile in the initial reaction of phenyl-2-propanone to yield intermediate A and classify the type of reaction that produces the final product from A.

Question 21

Show how each of the following transformations might be best accomplished. More than one step may be required. Show all reagents and all intermediate structures.
Refer to instructions.

Question 22

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

A)
B)
C)
D)

Question 23

Predict the major organic product obtained from the following sequence of reactions.

Question 24

Show how each of the following transformations might be best accomplished. More than one step may be required. Show all reagents and all intermediate structures.
Refer to instructions.

Question 25

Instructions: Give the major organic product(s) of each of the following reaction or sequence of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 26

What is the IUPAC name of the following compound?

A) (R)-4-amino-2-methylhexane
B) (S)-4-amino-2-methylhexane
C) N-ethyl N-(3-methylpropyl) amine
D) (R)-3-amino-5-methylhexane

Question 27

Instructions: Give the major organic product(s) of each of the following reaction or sequence of reactions. Show all relevant stereochemistry.
Give major product(s):

Question 28

Show how each of the following transformations might be best accomplished. More than one step may be required. Show all reagents and all intermediate structures.
Refer to instructions.

Question 29

Instructions: Give the major organic product(s) of each of the following reaction or sequence of reactions. Show all relevant stereochemistry.
Give the major product(s).

Question 30

Which of the following compounds are tertiary (3 $\degree$ ) amines?
1. (CH₃)₂CHN(CH₃)₂
2. CH₃CH(CH₃)N(CH₂CH₃)₂
3. CH₃CH₂CH₂NHCH₃
4. CH₃CH₂CH₂CH₂CH₂NH₂

A) 1 and 2
B) 1 and 3
C) 1, 2 and 3
D) 1, 2, 3 and 4

Question 31

Which of the following compounds are primary (1 $\degree$ ) amines?

A) 1 and 2
B) 1 and 3
C) 1, 2 and 3
D) 1, 2, 3 and 4

Question 32

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

A)
B)
C)
D)