Question 1

Which of the following statements about Lewis structures is correct?

Accepted Answer

Lewis structures represent all valence electrons, including lone pairs, using dots and lines.

Question 2

A molecule of acetic acid ($$\mathrm{CH_3COOH}) is $$dissolved in water. Which of the following best describes the acid-base equilibrium that occurs?

Accepted Answer

Acetic acid donates a proton to water, forming $$\mathrm{CH_3COO^-}$$ and $$\mathrm{H_3O^+}.$$

Question 3

Which of the following is the correct order of increasing acidity for the following compounds: $$\mathrm{CH_4$}$$, $$\mathrm{NH_3$}$$, $$\mathrm{H_2O}$$, $$\mathrm{HF}$$?

Accepted Answer

$$\mathrm{CH_4$} \u003c \mathrm{NH_3$} \u003c \mathrm{H_2O} \u003c \mathrm{HF}$$

Question 4

Which of the following best describes a conformer of cyclohexane in its most stable form?

Accepted Answer

Chair conformer, with all hydrogens staggered.

Question 5

A compound has a chiral center but is optically inactive. Which of the following best explains this observation?

Accepted Answer

The compound is a meso compound.

Question 6

Which of the following statements about SN2 reactions is correct?

Accepted Answer

SN2 reactions are favored by strong nucleophiles and primary alkyl halides.

Question 7

Given the following reaction: $$\mathrm{2~Br_2$ + 2~NaI \rightarrow 2~NaBr + I_2$}$$, which species is oxidized?

Accepted Answer

$$\mathrm{NaI}$$

Question 8

Which of the following best describes the stereochemistry outcome of a syn addition to an alkene?

Accepted Answer

Both substituents add to the same side of the double bond.

Question 9

Which of the following is a correct statement about aromaticity?

Accepted Answer

Aromatic compounds must have a planar ring and $$4n+2$$ $$\pi$$ electrons.

Question 10

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

Accepted Answer

$$\mathrm{F^-}$$

Question 11

A student is asked to draw the mechanism for the acid-catalyzed hydration of 2-butene. Which of the following is the correct first step?

Accepted Answer

Protonation of the double bond to form a carbocation.

Question 12

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 stabilization from surrounding alkyl groups.

Question 13

Which of the following reactions is an example of a pericyclic reaction?

Accepted Answer

Diels-Alder reaction

Question 14

Which of the following is the correct product of the retrosynthetic analysis of ethyl acetate ($$\mathrm{CH_3COOCH_2CH_3}$$)?

Accepted Answer

Acetic acid and ethanol

Question 15

Which of the following statements about the E1 reaction mechanism is correct?

Accepted Answer

The E1 mechanism proceeds via a carbocation intermediate.

Question 16

A compound is found to rotate plane-polarized light to the right. Which of the following terms best describes this compound?

Accepted Answer

Dextrorotatory

Question 17

Which of the following is the best description of a meso compound?

Accepted Answer

A compound with chiral centers that is optically inactive due to an internal plane of symmetry.

Question 18

Which of the following is the correct curved arrow mechanism for the nucleophilic addition of $$\mathrm{$$NaBH_4$$} to a $$carbonyl group?

Accepted Answer

Hydride from $$\mathrm{$$NaBH_4$$}$$ attacks the carbonyl carbon, pushing electrons onto the oxygen.

Question 19

Which of the following best explains why benzene does not undergo addition reactions like alkenes?

Accepted Answer

Benzene is stabilized by resonance and aromaticity, making addition reactions energetically unfavorable.

Question 20

Which of the following is the correct order of increasing nucleophilicity in protic solvents: $$\mathrm{F^-}$$, $$\mathrm{Cl^-}$$, $$\mathrm{Br^-}$$, $$\mathrm{I^-}$$?

Accepted Answer

$$\mathrm{F^-} \u003c \mathrm{Cl^-} \u003c \mathrm{Br^-} \u003c \mathrm{I^-}$$

Organic Chemistry I: Course Syllabus and Topic Overview

Study Guide - Practice Questions

Study Guide - Flashcards