Deck 18: Amines and Heterocycles

Question 1

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

Answer 1

Question 2

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

Answer 2

Question 3

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

Answer 3

CH₃CH₂CH₂NH₂
Strongest base because it is the only aliphatic amine. Weakest based because it is an amide not an amine and is not considered basic.

Question 4

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

Question 5

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 6

The pK_a of the 4-methoxyanilinium ion is 5.34. What is the pK_b for 4-methoxyaniline?

Question 7

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 8

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 9

The pK_a of aniline is 6.15. What percent exists in the neutral and protonated forms in a 0.00100 M solution of aniline at pH 5.75?

Question 10

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

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 12

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

Question 13

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

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

Question 15

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

Question 16

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

Question 17

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

Question 18

Refer to the table of pK_as below to answer the following question.pK_as of Some Arylammonium Ions
Refer to instructions. Based on the pK_as for their corresponding ammonium ions, which arylamine above is the strongest base?

Question 19

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 20

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

Question 21

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

Question 22

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

A)

B)

C)

D)

Question 23

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 24

Consider the reaction below to answer the following questions. a)What is the major organic product obtained from the reaction?
a.

b.

c.

d.

b)
How could IR spectroscopy be used to verify the identity of the product?

Question 25

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

Which of the following compounds are primary (1°) amines?

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

Question 27

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

A)

B)

C)

D)

Question 28

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 correct assignment of the names of the following aromatic compounds?

A) 1 = anisole; 2 = furan; 3 = pyrimidine
B) 1 = aniline; 2 = pyrrole; 3 = pyridine
C) 1 = anisole; 2 = pyridine; 3 = pyrrole
D) 1 = aniline; 2 = imidazole; 3 = pyridine

Question 30

Spectral analysis of the following compound included an IR and ¹H NMR. Which of the following would be evident in this analysis?

A) Lack of defining features in the ¹H NMR
B) Strong singlet in the ¹H NMR at about δ 2.2
C) Pair of bands in the IR between 3350 and 3450 cm−¹
D) Single band in the IR between 3350 and 3450 cm−¹
E) Both b and d

Question 31

What is the m/z for the α-cleavage of the following amine?

Question 32

The IR spectrum below was obtained for an unknown compound known to be an amine. How would this compound be classified based on the IR spectrum?

A) primary amine
B) secondary amine
C) tertiary amine
D) quaternary ammonium salt

Question 33

Circle any of the following compounds, that when used as the starting material and treated as shown below, would produce a single product.

Question 34

Which of the following compounds are tertiary (3°) 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 35

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

A)

B)

C)

D)

Question 36

Propose a structure that is consistent with the following spectral data:
MS:
M⁺ at m/z = 77
IR:
3350 cm−¹ (weak, single band)
¹H NMR:
δ1.05 (br s, 1H), δ1.15 (t, 6H), δ2.65 (q, 4H)