Question 1

Which of the following best describes the role of potassium hydroxide (KOH) in the synthesis of Nerolin from 2-naphthol?

Accepted Answer

KOH deprotonates 2-naphthol, generating a nucleophilic naphthoxide ion.

Question 2

In the SN2 mechanism for the synthesis of Nerolin, which step is rate-determining?

Accepted Answer

Nucleophilic attack by naphthoxide ion on iodoethane.

Question 3

Which solvent is most suitable for the SN2 synthesis of Nerolin, and why?

Accepted Answer

Ethanol, because it dissolves both KOH and organic reactants and allows the reaction to proceed.

Question 4

Which of the following statements about the SN2 reaction mechanism is correct?

Accepted Answer

The SN2 mechanism is a single-step process where the nucleophile attacks as the leaving group departs.

Question 5

Given the following rate law for an SN2 reaction: $$	ext{Rate} = k[	ext{substrate}][	ext{nucleophile}]$$, what would happen to the rate if the concentration of the nucleophile is doubled?

Accepted Answer

The rate would double.

Question 6

Which of the following is the best leaving group for an SN2 reaction?

Accepted Answer

Iodide ($$\mathrm{I^-})$$

Question 7

Why is phenol much more acidic than cyclohexanol?

Accepted Answer

Phenol is more acidic because its conjugate base is stabilized by resonance.

Question 8

Which IR absorption would you expect to disappear after converting 2-naphthol to Nerolin?

Accepted Answer

A strong O-H stretch around 3200–3600 cm$$^{-1}$$

Question 9

Which of the following would NOT be expected to react via an SN2 mechanism?

Accepted Answer

Tertiary alkyl chloride ($$\mathrm{(CH_3$)_3CCl})$$

Question 10

In the Williamson ether synthesis, why are secondary alkyl halides less efficient than primary alkyl halides?

Accepted Answer

Secondary alkyl halides are more likely to undergo elimination reactions.

Question 11

Which of the following best describes the nucleophile in the Nerolin synthesis?

Accepted Answer

2-naphthoxide ion

Question 12

What is the main safety concern when handling potassium hydroxide in the lab?

Accepted Answer

It is corrosive and toxic; skin contact should be avoided.

Question 13

Which of the following is a correct curved arrow mechanism for the SN2 reaction between hydroxide and iodomethane?

Accepted Answer

The hydroxide attacks the carbon of iodomethane as the iodide leaves, all in one step.

Question 14

Which factor most increases the rate of an SN2 reaction?

Accepted Answer

Using a strong, negatively charged nucleophile.

Question 15

What is the function of the reflux condenser in the Nerolin synthesis experiment?

Accepted Answer

It prevents evaporation of volatile reactants by condensing vapors back into the reaction flask.

Question 16

Which of the following is the correct product of the SN2 reaction between 2-naphthoxide and iodoethane?

Accepted Answer

2-ethoxynaphthalene (Nerolin)

Question 17

Which of the following is NOT a proper waste disposal practice in the organic lab?

Accepted Answer

Pouring liquid chemical waste down the drain.

Question 18

Which IR spectral feature would you use to distinguish between 2-naphthol and Nerolin?

Accepted Answer

Presence of a broad O-H stretch in 2-naphthol around 3200–3600 cm$$^{-1}$$

Nerolin Synthesis and Nucleophilic Substitution: SN2 Mechanism and Laboratory Practice

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