Question 1

Which of the following functional groups is NOT present in the molecule shown in the study materials (contains a benzene ring, a ketone, a sulfide, and a tertiary carbon center)?

Accepted Answer

Aldehyde

Question 2

Which prefix corresponds to a hydrocarbon chain containing 12 carbon atoms?

Accepted Answer

dodec-

Question 3

In resonance structures, which of the following preferences is MOST important for determining the major contributor?

Accepted Answer

Complete valence shells for all atoms

Question 4

Which resonance structure is most stable when comparing structures with a negative charge on oxygen versus carbon? Assume all other factors are equal.

Accepted Answer

Negative charge on oxygen

Question 5

Which of the following is the correct structure for a tert-butyl group?

Accepted Answer

$$\mathrm{R}-C(CH_3$)_3$$

Question 6

Which of the following statements about resonance contributors is TRUE?

Accepted Answer

Structures with no charge separation generally contribute more to the resonance hybrid.

Question 7

A resonance structure places a positive charge on a nitrogen atom with a complete octet. Which statement best describes its stability?

Accepted Answer

It is more stable than a structure with a positive charge on carbon.

Question 8

Which of the following is the correct arrow-pushing mechanism for converting an allylic lone pair to an allylic cation?

Accepted Answer

Use two curly arrows: one from the lone pair to the adjacent bond, and one from the bond to the next atom.

Question 9

Which of the following best describes hyperconjugation in carbocation stability?

Accepted Answer

Delocalization of electrons from neighboring sigma bonds into the empty p orbital of the carbocation

Question 10

A molecule contains a five-membered ring with three double bonds. Which functional group is present?

Accepted Answer

Cyclopentadienyl

Question 11

Which of the following resonance structures is the major contributor for the nitrosyl cation ($$\mathrm{NO}^+$$)?

Accepted Answer

The structure with a double bond between N and O and a positive charge on O

Question 12

Which of the following is NOT a correct rule for drawing resonance structures?

Accepted Answer

Arrows can flow in both directions simultaneously.

Question 13

Which of the following is the correct structure for a sulfide functional group?

Accepted Answer

$$\mathrm{R}-S-R'$$

Question 14

Which of the following resonance contributors is favored when considering charge separation?

Accepted Answer

The structure with no charge separation

Question 15

Which of the following is the correct arrow-pushing mechanism for a pi bond between atoms of differing electronegativity?

Accepted Answer

Curly arrow from the pi bond to the more electronegative atom

Question 16

Which of the following is NOT a correct resonance preference?

Accepted Answer

Place positive charge on the more electronegative atom

Question 17

Which of the following is the correct structure for a propyl group?

Accepted Answer

$$\mathrm{R}-CH_2CH_2CH_3$$

Question 18

Which of the following is TRUE about resonance hybrids?

Accepted Answer

Resonance hybrids show delocalized electrons using dashed lines and partial charges.

Question 19

Which of the following is the correct structure for an ethyl group?

Accepted Answer

$$\mathrm{R}-CH_2CH_3$$

Question 20

Which of the following statements about carbocation stability is correct?

Accepted Answer

Tertiary carbocations are more stable than secondary and primary carbocations due to hyperconjugation.

Organic Chemistry: Functional Groups, Resonance, and Stability

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