Question 1

Which of the following statements best describes resonance structures in organic molecules?

Accepted Answer

Resonance structures depict different possible arrangements of electrons within the same connectivity, illustrating electron delocalization.

Question 2

Which of the following is the most stable resonance contributor for the acetate ion ($$\mathrm{CH_3COO^-}$$)?

Accepted Answer

The structure with a negative charge delocalized equally between both oxygen atoms.

Question 3

Which of the following factors increases the acidity of a compound?

Accepted Answer

Increasing the resonance stabilization of the conjugate base.

Question 4

A student is asked to rank the acidity of the following compounds: phenol ($$\mathrm{C_6H_5OH}$$), ethanol ($$\mathrm{C_2H_5OH}$$), and acetic acid ($$\mathrm{CH_3COOH}). $$Which is the correct order from most acidic to least acidic?

Accepted Answer

Acetic acid \u003e phenol \u003e ethanol

Question 5

Which of the following statements about nucleophiles is correct?

Accepted Answer

Nucleophiles are species that donate an electron pair to form a new covalent bond.

Question 6

In an $$\mathrm{S_N2}$$ reaction, which of the following factors will increase the rate of reaction?

Accepted Answer

Using a strong nucleophile and a primary alkyl halide.

Question 7

Which of the following is the best explanation for why tertiary alkyl halides undergo $$\mathrm{S_N1}$$ reactions more readily than primary alkyl halides?

Accepted Answer

Tertiary carbocations are more stabilized by hyperconjugation and inductive effects.

Question 8

Which of the following is a correct statement about the Diels-Alder reaction?

Accepted Answer

It forms a six-membered ring by the concerted reaction of a diene and a dienophile.

Question 9

Which of the following alkyl halides will react fastest in an $$\mathrm{S_N2}$$ reaction?

Accepted Answer

1-bromopropane

Question 10

A chemist wants to synthesize tert-butyl chloride from tert-butyl alcohol. Which reagent would be most effective?

Accepted Answer

Hydrochloric acid ($$\mathrm{HCl})$$

Question 11

Which of the following statements about $$\mathrm{E2}$$ elimination reactions is correct?

Accepted Answer

The reaction requires a strong base and a good leaving group.

Question 12

Which of the following is the major product when 2-bromobutane is treated with a strong base such as $$\mathrm{KOH}$$?

Accepted Answer

2-butene (major, via Zaitsev's rule)

Question 13

Which of the following best explains why $$\mathrm{S_N1}$$ reactions are faster in polar protic solvents?

Accepted Answer

Polar protic solvents stabilize the carbocation intermediate and the leaving group.

Question 14

Which of the following is the best nucleophile in a polar aprotic solvent?

Accepted Answer

$$\mathrm{F^-}$$

Question 15

Which of the following statements about the reactivity of alkyl halides in $$\mathrm{S_N1}$$ and $$\mathrm{S_N2}$$ reactions is correct?

Accepted Answer

Primary alkyl halides react fastest in $$\mathrm{S_N2}$$ reactions.

Question 16

Which of the following is a correct statement about the effect of resonance on the basicity of amines?

Accepted Answer

Resonance decreases the basicity of amines by delocalizing the lone pair.

Question 17

Which of the following is the correct product of the reaction between 1-bromopropane and sodium cyanide ($$\mathrm{NaCN}) in $$ethanol?

Accepted Answer

1-cyanopropane ($$\mathrm{CH_3CH_2CH_2CN})$$

Question 18

Which of the following statements about the Zaitsev rule is correct?

Accepted Answer

The Zaitsev rule predicts that the most substituted alkene will be the major product.

Question 19

Which of the following is the best explanation for why $$\mathrm{E1}$$ reactions are favored by weak bases?

Accepted Answer

Weak bases stabilize the carbocation intermediate formed during the reaction.

Organic Chemistry I: Unit 3 Evaluation Review Guide – Study Notes

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