Question 1

Which of the following statements best explains why $$\ce{I^-} is a $$better nucleophile than $$\ce{F^-} in a $$protic solvent?

Accepted Answer

Because $$\ce{I^-} is $$less basic and more easily solvated, making it less hindered by hydrogen bonding.

Question 2

A chemist wants to selectively reduce a ketone in the presence of an ester. Which of the following strategies would best achieve this selectivity?

Accepted Answer

Protect the ketone as a ketal, reduce the ester, then deprotect the ketone.

Question 3

Which of the following compounds is most likely to undergo an $$\mathrm{S_N1}$$ reaction?

Accepted Answer

A tertiary alkyl halide in a polar protic solvent

Question 4

Which of the following best describes the role of a Lewis acid in an organic reaction?

Accepted Answer

It accepts an electron pair to form a coordinate covalent bond.

Question 5

A student is attempting to oxidize a primary alcohol to a carboxylic acid. Which reagent would be most appropriate for this transformation?

Accepted Answer

$$\ce{CrO3} in $$aqueous acid

Question 6

Which of the following functional groups is the most oxidized?

Accepted Answer

Carboxylic acid

Question 7

In an $$\mathrm{S_N2}$$ reaction, what is the stereochemical outcome at the reactive center?

Accepted Answer

Inversion of configuration

Question 8

Which of the following is NOT a characteristic of a good leaving group?

Accepted Answer

Strong base

Question 9

A reaction converts a secondary alcohol to a ketone. Which type of reagent is required for this transformation?

Accepted Answer

An oxidizing agent

Question 10

Which of the following best explains why tertiary alkyl halides do not undergo $$\mathrm{S_N2}$$ reactions efficiently?

Accepted Answer

Steric hindrance prevents backside attack by the nucleophile.

Question 11

Which of the following statements about nucleophilicity and basicity is correct?

Accepted Answer

Nucleophilicity is a kinetic property, while basicity is a thermodynamic property.

Question 12

Which of the following is the best explanation for why $$\ce{Br^-} is a $$better leaving group than $$\ce{HO^-}$$?

Accepted Answer

$$\ce{Br^-} is $$the conjugate base of a strong acid and is more stable in solution.

Question 13

A molecule contains both an aldehyde and a primary alcohol. When treated with $$\ce{NaBH4}$$, which functional group will be reduced?

Accepted Answer

The aldehyde only

Question 14

Which of the following best describes the effect of resonance stabilization on leaving group ability?

Accepted Answer

It increases leaving group ability by stabilizing the negative charge.

Question 15

Which of the following is the correct order of increasing electrophilicity for the following compounds: alkane, aldehyde, carboxylic acid, ketone?

Accepted Answer

Alkane \u003c aldehyde \u003c ketone \u003c carboxylic acid

Question 16

A peptide bond is formed between two amino acids. Which type of reaction is this, and what is the leaving group?

Accepted Answer

Nucleophilic acyl substitution; water

Question 17

Which of the following solvents would most likely increase the rate of an $$\mathrm{S_N2}$$ reaction?

Accepted Answer

A polar aprotic solvent such as $$\ce{DMSO}$$

Question 18

Which of the following best describes the first step in an acid-catalyzed nucleophilic addition to a carbonyl compound?

Accepted Answer

Protonation of the carbonyl oxygen

Question 19

A chemist wants to convert an ester to a carboxylic acid. Which of the following reagents would be most effective?

Accepted Answer

Aqueous acid or base (hydrolysis)

Question 20

Which of the following is the best explanation for why $$\ce{CH3COO^-} is a $$better leaving group than $$\ce{HO^-}$$?

Accepted Answer

$\ce{CH3COO^-}$$ is resonance stabilized, making it more stable in solution.

Kaplan ch 4

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