1.17: Quiz 3B

1. Clearly indicate true (T) or false (F) for the following statements (2 pts each):

2. Multiple Choice: (2 pts each)

Which of the following molecules has a conjugated pi system?

Which of the following statements are correct concerning delocalized electrons?

1. Electrons do not belong to a single atom.
2. Electrons are not confined to a bond between two atoms
3. Electrons are shared by three or more atoms
4. A, B and C
5. A and B

The delocalized π system in benzene is formed by a cyclic overlap of 6 _______ orbitals.

1. sp
2. sp²
3. sp³
4. s
5. p

Which of the following statements is incorrect about benzene?

1. It has delocalized electrons
2. The carbon-carbon bond lengths are all the same
3. All six atoms lie in the same plane
4. All of the carbon atoms are sp hybridized

Which of the following compounds is not a Lewis base?

1. BF₃
2. NH₃
3. CH₃OCH₃
4. CH₃OH

Which arrow is used to represent two contributors in a resonance hybrid?

3. (6 pts) Consider the following two compounds (A and B) and circle which compound will have the highest boiling point. Briefly explain your answer, including the intermolecular forces for each.

4. Delocalized electrons and resonance (11 pts total)
   1. Circle any of the following compounds that have a nitrogen atom with delocalized electrons.

2. For each pair of resonance structures shown below (A and B), circle which resonance contributor makes a greater contribution to the resonance hybrid. Briefly explain your answer.

5. 1. (4 pts) Which compound (A or B) is a stronger acid? Provide a brief explanation for your answer.

2. (4 pts) Lactic acid (also know as milk acid) has two acidic protons (A and B). Explain which proton is more acidic and draw the conjugate base that will result upon deprotonation.

   

6. (6 pts) The following molecule has an acidic proton. Draw the conjugate base for this molecule and then show why this molecule is acidic by drawing a relevant resonance structure.

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