Q: Which of the following is the correct order of radical stability?

Methyl < Primary < Secondary < Tertiary

Q: A student is asked to predict the direction of the following acid-base reaction at equilibrium: $CH_3CH_2OH + H_2SO_4 \rightarrow CH_3CH_2OSO_3H + H_2O$. Which factor should they consider?

Compare the pKa values of the acids on both sides

Q: Which of the following best describes the product formed when cyclohexene reacts with $Br_2$ in water?

Trans-1,2-bromohydroxycyclohexane

Q: Which of the following mechanisms explains the anti-addition observed in the reaction of alkenes with $Br_2$?

Formation and opening of a bromonium ion intermediate

Q: Which of the following steps is required to complete the hydration of an alkene using $Hg(OAc)_2$ followed by $NaBH_4$?

Reduction of the mercurinium ion intermediate

Question 1

Which of the following best describes the role of ammonia ($NH_3$) in the reaction with hydrogen chloride ($HCl$) according to the Brønsted-Lowry definition?

Accepted Answer

Brønsted-Lowry base

Question 2

Consider the reaction: $CH_3COOH + H_2O \rightarrow CH_3COO^- + H_3O^+$. Which species is the conjugate base?

Accepted Answer

$CH_3COO^-$

Question 3

Which of the following factors increases the acidity of a molecule by stabilizing its conjugate base through induction?

Accepted Answer

Presence of highly electronegative atoms near the acidic proton

Question 4

Given the following pKa values: alkane ($\sim$50), alkene ($\sim$44), alkyne ($\sim$25), which is the most acidic?

Accepted Answer

Alkyne

Question 5

Which of the following best explains why acetic acid ($CH_3COOH$) is more acidic than ethanol ($CH_3CH_2OH$)?

Accepted Answer

Acetic acid has more resonance stabilization in its conjugate base

Question 6

Which of the following curved arrow mechanisms correctly represents the first step in the addition of $HBr$ to an alkene?

Accepted Answer

Arrow from alkene $ightarrow$ $H$ of $HBr$

Question 7

Which of the following statements about carbocation stability is correct?

Accepted Answer

Tertiary carbocations are stabilized by hyperconjugation and inductive effects

Question 8

In the halogenation of methane with $Cl_2$, which step involves a single-electron ('single hook') arrow?

Accepted Answer

Initiation step: $Cl_2 \rightarrow 2Cl\cdot$

Question 9

Which of the following best predicts the major product when 2-methylpropene reacts with $HBr$?

Accepted Answer

2-bromo-2-methylpropane

Question 10

Which of the following is the correct order of radical stability?

Accepted Answer

Methyl < Primary < Secondary < Tertiary

Question 11

A student is asked to predict the direction of the following acid-base reaction at equilibrium: $CH_3CH_2OH + H_2SO_4 \rightarrow CH_3CH_2OSO_3H + H_2O$. Which factor should they consider?

Accepted Answer

Compare the pKa values of the acids on both sides

Question 12

Which of the following best describes the product formed when cyclohexene reacts with $Br_2$ in water?

Accepted Answer

Trans-1,2-bromohydroxycyclohexane

Question 13

Which of the following mechanisms explains the anti-addition observed in the reaction of alkenes with $Br_2$?

Accepted Answer

Formation and opening of a bromonium ion intermediate

Question 14

Which reagent is used to convert an alkene to an epoxide?

Accepted Answer

Peracid (e.g., $m$-CPBA)

Question 15

Which of the following best describes the product of the hydroboration-oxidation of 1-hexene?

Accepted Answer

2-hexanol

Question 16

Which of the following steps is required to complete the hydration of an alkene using $Hg(OAc)_2$ followed by $NaBH_4$?

Accepted Answer

Reduction of the mercurinium ion intermediate

Question 17

Which of the following statements about the hybridization effect on acidity is correct?

Accepted Answer

An sp-hybridized carbon is more acidic than an sp2-hybridized carbon

Question 18

Which of the following is the correct mechanism for the addition of water to an alkene in dilute acid?

Accepted Answer

Protonation of the alkene, formation of carbocation, nucleophilic attack by water, deprotonation

Question 19

Which of the following is the major product when phenylacetylene reacts with excess $HBr$?

Accepted Answer

1,1-dibromo-2-phenylethane

Organic Chemistry Exam 2 Study Guide: Acids, Bases, Reaction Mechanisms, and Alkene/Alkyne Chemistry

Study Guide - Practice Questions

Study Guide - Flashcards