Question 1

Which of the following best describes the mechanism by which nerolin is synthesized from 2-naphthol and iodoethane?

Accepted Answer

An $$\mathrm{S_N2}$$ nucleophilic substitution, where the nucleophile attacks as the leaving group departs in a single concerted step.

Question 2

In the synthesis of nerolin, what is the role of potassium hydroxide ($$\mathrm{KOH}$$)?

Accepted Answer

It acts as a base to deprotonate 2-naphthol, generating the nucleophilic 2-naphthoxide ion.

Question 3

Why is potassium hydroxide ($$\mathrm{KOH}) $$preferred over sodium hydroxide ($$\mathrm{NaOH}) in $$the nerolin synthesis?

Accepted Answer

Potassium hydroxide is more soluble in ethanol, the solvent used for the reaction.

Question 4

What is the nucleophile in the reaction that produces nerolin?

Accepted Answer

2-naphthoxide ion ($$\mathrm{C$$_{10}$$H_7O^-})$$

Question 5

Which of the following is the correct balanced chemical equation for the synthesis of nerolin?

Accepted Answer

$$\mathrm{C$$_{10}$$H_7OH} + \mathrm{C_2H_5I} + \mathrm{KOH} \rightarrow \mathrm{C$$_{10}$$H_7OC_2H_5} + \mathrm{KI} + \mathrm{H_2O}$$

Question 6

What is the leaving group in the nucleophilic substitution reaction that forms nerolin?

Accepted Answer

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

Question 7

If the filtered nerolin product is not properly dried before weighing, what is the most likely effect on the calculated percent yield?

Accepted Answer

The percent yield will be artificially high due to the presence of water.

Question 8

During the synthesis, why is it important to use equimolar amounts of 2-naphthoxide ion and iodoethane?

Accepted Answer

To ensure complete reaction and maximize the yield of nerolin.

Question 9

Which of the following best explains why nerolin precipitates upon addition of ice-cold water after the reaction?

Accepted Answer

Nerolin is less soluble in water and ethanol at low temperatures, causing it to crystallize.

Question 10

Which safety precaution is most important when handling potassium hydroxide in this experiment?

Accepted Answer

Wear safety goggles and wash thoroughly if skin contact occurs, as potassium hydroxide is corrosive and toxic.

Question 11

Which of the following statements about the $$\mathrm{S_N2}$$ mechanism is correct?

Accepted Answer

The nucleophile attacks the substrate at the same time as the leaving group departs, resulting in inversion of configuration at the reaction center.

Question 12

Suppose you obtained a melting point for your nerolin product that was significantly lower and broader than the literature value. What is the most likely explanation?

Accepted Answer

The product is impure, possibly containing water or other contaminants.

Question 13

Which of the following would NOT be a plausible reason for a low percent yield in the nerolin synthesis?

Accepted Answer

All reactants were completely converted to product.

Question 14

In the context of the nerolin synthesis, which of the following best describes the function of ethanol?

Accepted Answer

It acts as a solvent for both the organic reactants and potassium hydroxide.

Question 15

Which of the following would be the best evidence that your product is indeed nerolin?

Accepted Answer

The melting point matches the literature value and FTIR analysis confirms the expected functional groups.

Question 16

If you used twice as much iodoethane as 2-naphthol in the reaction, what would you expect to observe?

Accepted Answer

No increase in nerolin yield, as the reaction is limited by the amount of 2-naphthol.

Question 17

Which of the following best explains why the $$\mathrm{S_N2}$$ mechanism is favored in the synthesis of nerolin?

Accepted Answer

The nucleophile (2-naphthoxide) is strong and the substrate (iodoethane) is a primary alkyl halide, both favoring $$\mathrm{S_N2}.$$

Question 18

Which of the following is a real-world application of nerolin?

Accepted Answer

It is used as a fixative in perfumes to slow the evaporation of volatile compounds.

Nucleophilic Substitution: Preparation of Nerolin (2-Ethoxynaphthalene)

Study Guide - Practice Questions

Study Guide - Flashcards