Q: What is the formula for calculating the degree of unsaturation (double bond equivalents) in a molecule?

$$\text{DU} = \frac{2C + 2 + N - H - X}{2}$$

Question 1

Which of the following best describes a Lewis acid?

Accepted Answer

A substance that accepts an electron pair in a chemical reaction.

Question 2

Given the following acids: acetic acid ($$\ce{CH3COOH}$$), hydrochloric acid ($$\ce{HCl}$$), and phenol ($$\ce{C6H5OH}$$), which is the strongest acid?

Accepted Answer

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

Question 3

Which of the following is an example of an amphoteric compound?

Accepted Answer

Water ($$\ce{H2O})$$

Question 4

If the $$pK_a of $$acid A is 4.8 and the $$pK_a of $$acid B is 2.3, which acid is stronger?

Accepted Answer

Acid B

Question 5

Which of the following statements about Gibbs free energy ($$\Delta G) is $$correct?

Accepted Answer

$$\Delta G is $$negative for a spontaneous reaction.

Question 6

What is the formula for calculating the degree of unsaturation (double bond equivalents) in a molecule?

Accepted Answer

$$	ext{DU} = \frac{2C + 2 + N - H - X}{2}$$

Question 7

Which of the following best describes the hybridization and geometry of the carbons in ethylene ($$\ce{CH2=CH2}$$)?

Accepted Answer

sp$$^2$$ hybridization, trigonal planar geometry

Question 8

Which of the following carbocations is the most stable?

Accepted Answer

Tertiary ($$3^\circ) $$carbocation

Question 9

Which reagent would you use to convert an alkene to a vicinal diol (two hydroxyl groups on adjacent carbons)?

Accepted Answer

OsO$$_4$$ followed by NaHSO$$_3$$

Question 10

In the hydration of an alkene using acid catalysis, which product is formed according to Markovnikov's rule?

Accepted Answer

The alcohol adds to the more substituted carbon.

Question 11

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

Accepted Answer

$$\ce{I^-}$$

Question 12

Which of the following reactions is an example of anti-Markovnikov addition?

Accepted Answer

Hydroboration-oxidation of an alkene

Question 13

What is the major product when 1-butene reacts with Br$$_2 in $$water?

Accepted Answer

2-bromo-1-butanol

Question 14

Which of the following best explains why tertiary carbocations are more stable than secondary or primary carbocations?

Accepted Answer

Tertiary carbocations have more hyperconjugation and inductive effects from surrounding alkyl groups.

Question 15

Which of the following is the correct mechanism for the bromination of an alkene?

Accepted Answer

Formation of a bromonium ion intermediate followed by nucleophilic attack by Br$$^-. $$

Question 16

Which of the following factors does NOT increase the acidity of a molecule?

Accepted Answer

Increasing electron-donating groups near the acidic proton.

Question 17

Which of the following is the correct product for the oxymercuration-demercuration of 1-methylcyclohexene?

Accepted Answer

1-methylcyclohexanol (alcohol at the more substituted carbon)

Question 18

Which of the following is the correct order of nucleophilicity in a polar aprotic solvent?

Accepted Answer

$$\ce{F^-} \u003e \ce{Cl^-} \u003e \ce{Br^-} \u003e \ce{I^-}$$

Question 19

Which of the following is the correct product for the hydroboration-oxidation of 1-hexene?

Accepted Answer

1-hexanol

Question 20

Which of the following statements about Markovnikov's rule is correct?

Accepted Answer

The hydrogen atom adds to the carbon with the most hydrogens already attached.

Organic Chemistry Exam Study Guide: Acids, Bases, Alkenes, and Reaction Mechanisms

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