Deck 25: Heterocycles: Heteroatoms in Cyclic Organic Compounds

Question 1

Predict the major product of the following reaction.

A)

B)

C)

D)

E)

Answer 1

Question 2

What product(s)would you obtain from the reaction below?

A)

B)

C)

D)

E)

Answer 2

Question 3

Indole is stabilized by several charge-separated resonance contributors.Which of the following is not a contributing charge-separated resonance structure?

A)

B)

C)

D)

E)

Answer 3

Question 4

Which atom in the following heterocycle would be the most basic?

A) A
B) B
C) C
D) D
E) E

Question 5

Which of the following would be the most basic?

A)

B)

C)

D)

E)

Question 6

What is the name of the following amine?

A) Piperidine
B) Pyrrolidine
C) Morpholine
D) Piperazine
E) Pyridine

Question 7

Which of the following would be the most reactive diene in a Diels-Alder reaction?

A)

B)

C)

D) These are equally reactive.
E) None of these undergo Diels-Alder reactions.

Question 8

Which of the chloroquinolines shown below would be most reactive toward sodium methoxide?

A)

B)

C)

D)

E) These are expected to be equally reactive.

Question 9

What product would be formed in the reaction below?

A)

B)

C)

D)

E)

Question 10

Which reagent might convert 2,5-hexanedione to 2,5-dimethylfuran?

A) NaBH₄,CH₃OH
B) H₂,Pt
C) NaOH,heat
D) P₂O₅
E) Na,EtOH

Question 11

How would the heterocyclic amines shown here be ranked in order of decreasing basicity (more basic > less basic)?

A) III > I > II
B) I > II > III
C) II > III > I
D) I > III > II
E) II > I > III

Question 12

Which of the following is not formed as either an intermediate along the reaction pathway or as a final product for the Chichibabin reaction shown below?

A)

B)

C)

D)

E)

Question 13

The best way to prepare a 2-alkylpyridine from pyridine would be what?

A) Electrophilic substitution
B) Free-radical substitution
C) Nucleophilic substitution
D) An S_N2 reaction
E) None of the above are correct.

Question 14

What product do you expect from the reaction shown below?

A)

B)

C)

D)

E)

Question 15

Which of the following structures represents a quinoline derivative?

A)

B)

C)

D)

E)

Question 16

Which of the following is not aromatic?

A)

B)

C)

D)

E) All are aromatic.

Question 17

Which nitrogen,if either,is the more basic in nicotine?

A) Nitrogen A is more basic.
B) Nitrogen B is more basic.
C) The nitrogens are equally basic.
D) Neither nitrogen is basic.
E) There is no basis on which to predict this.

Question 18

Predict the major product of the following reaction.

A)

B)

C)

D)

E)

Question 19

You would expect a very strong nucleophile (e.g.,H₂N^-)to attack 2-methylpyridine where?

A) Position a
B) Position b
C) Position c
D) Position d
E) Position e

Question 20

You would expect a powerful electrophile (e.g.,Br⁺)to attack 2-methylpyridine mostly at which carbon?

A) Position a
B) Position b
C) Position c
D) Position d
E) Position e

Question 21

Which of the following compounds is not a heterocycle?

A)

B)

C)

D)

E)

Question 22

What is the product of the following reaction?

A)

B)

C)

D)

E) None of the above.

Question 23

Which of the following compounds is not an alkaloid?

A)

B)

C)

D)

E) All of the above are alkaloids.