Question 1

Which of the following statements best explains why $$\mathrm{CH_3C \equiv NH} is $$more acidic than $$\mathrm{CH_3CH = NH_2$^+}$$ and $$\mathrm{CH_3CH_2NH_3^+}$$?

Accepted Answer

The sp-hybridized nitrogen in $$\mathrm{CH_3C \equiv NH} is $$more electronegative, stabilizing the conjugate base.

Question 2

Given the equilibrium $$\mathrm{CH_3C \equiv CH + B^- \rightleftharpoons CH_3C \equiv C^- + BH}$$, which base would most favor product formation?

Accepted Answer

$$\mathrm{NH_2$^-}$$

Question 3

Which compound is the conjugate base of methanol ($$\mathrm{CH_3OH}$$)?

Accepted Answer

$$\mathrm{CH_3O^-}$$

Question 4

Which of the following correctly ranks the acidity of the following species: $$\mathrm{CH_3C \equiv NH}$$, $$\mathrm{CH_3CH = NH_2$^+}$$, $$\mathrm{CH_3CH_2NH_3^+}$$?

Accepted Answer

$$\mathrm{CH_3C \equiv NH \u003e CH_3CH = NH_2$^+ \u003e CH_3CH_2NH_3^+}$$

Question 5

Which of the following is the strongest base among the following: $$\mathrm{OH^-}$$, $$\mathrm{CH_3O^-}$$, $$\mathrm{NH_2$^-}$$, $$\mathrm{CH_3CO_2^-}$$?

Accepted Answer

$$\mathrm{NH_2$^-}$$

Question 6

A student is asked to deprotonate $$\mathrm{CH_3C \equiv CH} in $$the laboratory. Which base should they choose to ensure the reaction goes to completion?

Accepted Answer

$$\mathrm{NH_2$^-}$$

Question 7

Which of the following statements about conjugate acids and bases is correct?

Accepted Answer

The weakest acid has the strongest conjugate base.

Question 8

Which of the following is the conjugate acid of $$\mathrm{CH_3O^-}$$?

Accepted Answer

$$\mathrm{CH_3OH}$$

Question 9

In a reaction where $$\mathrm{CH_3CH_2NH_3^+}$$ acts as an acid, what is the likely product after deprotonation?

Accepted Answer

$$\mathrm{CH_3CH_2NH_2}$$

Question 10

Which of the following best describes why $$\mathrm{NH_2$^-} is a $$stronger base than $$\mathrm{OH^-}$$?

Accepted Answer

Nitrogen is less electronegative than oxygen, so it holds negative charge less tightly.

Question 11

Which of the following is the correct conjugate acid-base pair?

Accepted Answer

$$\mathrm{CH_3OH}$$ / $$\mathrm{CH_3O^-}$$

Question 12

A chemist wants to generate $$\mathrm{CH_3C \equiv C^-}$$ for a nucleophilic addition reaction. Which base should be used?

Accepted Answer

$$\mathrm{NH_2$^-}$$

Question 13

Which of the following is the weakest acid?

Accepted Answer

$$\mathrm{CH_3CH_2NH_3^+}$$

Question 14

Which of the following is the correct order of base strength for the conjugate bases of the acids in the image?

Accepted Answer

$$\mathrm{CH_3CH_2NH_2 \u003e CH_3CH = NH \u003e CH_3C \equiv N}$$

Acids, Bases, and Conjugate Pairs in Organic Chemistry

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