Question 1

Which of the following compounds is the most acidic? Consider resonance stabilization and inductive effects.

A) $$CH_3CH_2OH

B$$) $$CH_3COOH

C$$) $$C_6H_5OH

D$$) $$CH_3CH_2NH_2$$

Accepted Answer

$$CH_3COOH$$

Question 2

Which of the following statements best explains why the carboxyl group ($$-COOH) is $$more acidic than the hydroxyl group ($$-OH$$)?

Accepted Answer

The carboxylate anion is stabilized by resonance.

Question 3

Which of the following is the correct order of acid strength from strongest to weakest?

A) $$CH_3COOH$$, $$C_6H_5OH$$, $$CH_3CH_2OH$$, $$CH_3CH_2NH_2$$

Accepted Answer

$$CH_3COOH \u003e C_6H_5OH \u003e CH_3CH_2OH \u003e CH_3CH_2NH_2$$

Question 4

Which of the following molecules has the greatest number of resonance structures?

A) Benzene ($$C_6H_6)

B) $$Acetone ($$CH_3COCH_3)

C) $$Ethene ($$C_2H_4)

D) $$Cyclohexane ($$C_6H_{12})$$

Accepted Answer

Benzene ($$C_6H_6)$$

Question 5

Which of the following is the slow (rate-determining) step in the mechanism of the acid-catalyzed hydration of 1-hexene?

A) Protonation of the alkene to form a carbocation

B) Nucleophilic attack by water

C) Deprotonation of the oxonium ion

D) Formation of the alkene

Accepted Answer

Protonation of the alkene to form a carbocation

Question 6

In the reaction of cyclohexene with $$H_2SO_4$$ and $$H_2O$$, what is the major product?

A) Cyclohexanol

B) Cyclohexene oxide

C) Cyclohexane

D) Cyclohexyl sulfate

Accepted Answer

Cyclohexanol

Question 7

Which of the following best describes the energy profile for a reaction with a high activation energy and a large negative $$	riangle G$$?

A) The reaction is fast and endergonic.

B) The reaction is slow and exergonic.

C) The reaction is fast and exergonic.

D) The reaction is slow and endergonic.

Accepted Answer

The reaction is slow and exergonic.

Question 8

Which of the following amino acids does NOT have a chiral center?

A) Glycine

B) Alanine

C) Serine

D) Threonine

Accepted Answer

Glycine

Question 9

Which of the following is a correct resonance structure for the acetate ion ($$CH_3COO^-$$)?

Accepted Answer

$$CH_3C(=O)O^-$$ and CH_3C(O^-)O$

Question 10

Which of the following statements about the periodic table is correct?

Accepted Answer

Elements in the same group have similar chemical properties due to similar valence electron configurations.

Question 11

Which of the following is the correct product for the reaction of 1-bromobutane with $$NaOH in $$water?

Accepted Answer

1-butanol

Question 12

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

Accepted Answer

Tertiary carbocations are stabilized by hyperconjugation and inductive effects from surrounding alkyl groups.

Question 13

Which of the following reactions is an example of a nucleophilic substitution ($$S_N2) $$mechanism?

Accepted Answer

Reaction of methyl bromide with hydroxide ion

Question 14

Which of the following is the correct order of base strength from strongest to weakest?

A) $$NH_2$$^-$$, OH$$^-$$, CH_3$$COO^-$$, Cl$$^-$$

Accepted Answer

$$NH_2$$^- \u003e OH^- \u003e CH_3COO^- \u003e Cl^-$$

Question 15

Which of the following is the major product when 2-methyl-2-butene reacts with $$HBr$$?

Accepted Answer

2-bromo-2-methylbutane

Question 16

Which of the following best describes the role of $$H_2SO_4 in $$the hydration of alkenes?

Accepted Answer

$$H_2SO_4$$ acts as a catalyst by donating a proton to the alkene.

Question 17

Which of the following is a correct statement about resonance structures?

Accepted Answer

Resonance structures are a way to represent delocalized electrons within a molecule.

Question 18

Which of the following is the correct product for the reaction of benzene with $$Br_2$$ and $$FeBr_3$$?

Accepted Answer

Bromobenzene

Question 19

Which of the following best explains why $$CH_3COOH is a $$stronger acid than $$C_6H_5OH$$?

Accepted Answer

$$CH_3COOH$$ has more resonance stabilization in its conjugate base.

Organic Chemistry Exam Study Guide: Acids, Bases, Mechanisms, Resonance, and Chirality

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