Question 1

Which of the following statements correctly describes the relationship between acid strength and the stability of its conjugate base?

Accepted Answer

A strong acid has a stable conjugate base because the negative charge is well stabilized, often by resonance or electronegativity.

Question 2

Given the following compounds, which is the strongest acid?

$$ \mathrm{CH_3COOH} $$, $$ \mathrm{CH_3CH_2OH} $$, $$ \mathrm{H_2O} $$, $$ \mathrm{NH_3$} $$

Accepted Answer

$$ \mathrm{CH_3COOH} $$

Question 3

Which of the following is the correct resonance structure for the acetate ion ($$ \mathrm{CH_3COO^-} $$)?

Accepted Answer

Both oxygen atoms share the negative charge equally, with one double bond and one single bond to carbon in each resonance form.

Question 4

Which of the following best describes the electron-pushing arrows in the mechanism of alkene hydration (acid-catalyzed addition of water to an alkene)?

Accepted Answer

The arrows show the movement of electron pairs from the alkene to a proton, then from water to the carbocation, and finally from water to a proton.

Question 5

Which of the following alkenes is the most stable?

Accepted Answer

Trans-2-butene

Question 6

What is the IUPAC name for the following compound?

$$ \mathrm{CH_2$=CHCH_2CH_3} $$

Accepted Answer

1-butene

Question 7

How many degrees of unsaturation are present in a molecule with the formula $$ \mathrm{C_5H_8} $$?

Accepted Answer

2

Question 8

Which of the following best describes the product(s) of the ozonolysis of 2-butene ($$ \mathrm{CH_3CH=$$CHCH_3$$} ) $$followed by reductive workup?

Accepted Answer

Two molecules of acetaldehyde ($$ \mathrm{CH_3CHO} )$$

Question 9

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

Accepted Answer

The hydrogen atom adds to the carbon of the double bond with the greater number of hydrogens already attached.

Question 10

Which of the following is the correct E/Z designation for the following alkene?

$$ \mathrm{CH_3CH=CHCH_2CH_3}  ($$the double bond is between C2 and C3)

Accepted Answer

E-2-pentene

Question 11

Which of the following statements about the stability of carbocations is correct?

Accepted Answer

A tertiary carbocation is more stable than a secondary or primary carbocation due to hyperconjugation and inductive effects.

Question 12

Which of the following best describes the mechanism of epoxidation of an alkene using a peroxyacid (e.g., mCPBA)?

Accepted Answer

A concerted reaction where the alkene reacts with the peroxyacid to form an epoxide and a carboxylic acid.

Question 13

Which of the following is the correct product of the hydration of 1-methylcyclohexene under acidic conditions?

Accepted Answer

1-methylcyclohexanol (with the OH group on the more substituted carbon)

Question 14

Which of the following best explains why trans-2-butene is more stable than cis-2-butene?

Accepted Answer

Trans-2-butene has less steric strain between the methyl groups than cis-2-butene.

Question 15

Which of the following is the correct IUPAC name for the compound with the structure:

$$ \mathrm{CH_2$=CHCH(CH_3$)CH_2CH_3} $$

Accepted Answer

3-methyl-1-pentene

Question 16

Which of the following best describes the role of resonance in stabilizing the conjugate base of phenol ($$ \mathrm{C_6H_5O^-} $$)?

Accepted Answer

The negative charge is delocalized over the aromatic ring through resonance, increasing stability.

Question 17

Which of the following is the correct product of the reaction of 1-butene with bromine ($$ \mathrm{Br_2$} ) in $$the presence of methanol ($$ \mathrm{CH_3OH} $$)?

Accepted Answer

1-bromo-2-methoxybutane

Question 18

Which of the following best describes the mechanism of oxymercuration-demercuration of alkenes?

Accepted Answer

It proceeds via a mercurinium ion intermediate, followed by nucleophilic attack and reduction to give Markovnikov addition of water without carbocation rearrangement.

Question 19

Which of the following is the conjugate acid of ammonia ($$ \mathrm{NH_3$} $$)?

Accepted Answer

$$ \mathrm{NH_4$^+} $$

Question 20

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

Accepted Answer

Tertiary radicals are stabilized by hyperconjugation and inductive effects from three alkyl groups.

Organic Chemistry Study Notes: Acids/Bases and Alkenes (Chapters 4-6)

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