Deck 12: Amines

Question 1

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

Answer 1

The nitrogen in mepiquat chloride is a quaternary ammonium salt.

Question 2

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.

Answer 2

The nucleophile is methylamine and the final (second) reaction is a reduction.

Question 3

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:

Answer 3

c.

Question 4

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

Question 5

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

Question 6

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

Question 7

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 8

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

Question 9

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

Question 10

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

Question 11

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

Question 12

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 13

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 14

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 15

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 16

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

Question 17

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

Question 18

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

Question 19

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 20

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

Question 21

Which of the following compounds are tertiary (3 $\degree$ ) amines? 1. $\quad\left(\mathrm{CH}_{3}\right)_2 \mathrm{CHN}\left(\mathrm{CH}_{3}\right)_{2}$
2. $\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{N}\left(\mathrm{CH}_{2} \mathrm{CH}_{3}\right)_{2}$
3. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NHCH}_{3}$
4. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}$

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

Question 22

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 23

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 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

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 26

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 27

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

Question 28

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 29

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

A)
B)
C)
D)

Question 30

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

A)
B)
C)
D)

Question 31

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