Deck 18: Amines and Heterocycles

Question 1

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):

Answer 1

Question 2

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):

Answer 2

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.Intermediate A is an example of:

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

Answer 3

an imine

Question 4

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

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

Question 5

Propose a structure that is consistent with the following spectral data:

Question 6

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

Question 7

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 8

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

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

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 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: 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 13

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 14

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

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: 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 17

Instructions: 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 18

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

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

Which of the following compounds are tertiary (3 ^$\circ$ )amines?

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

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

Consider the reaction below to answer the following questions.

a) What is the major organic procuct obtained from the reaction?
a.
b.
c.
d.

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

Question 24

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

A)
B)
C)
D)

Question 25

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 d 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 26

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

A)
B)
C)
D)

Question 27

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?
Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology,11-13-08)

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

Question 28

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