This is my work just in case you need some info, but I need help badly. http://w

Question

This is my work just in case you need some info, but I need help badly. http://www.chem.umass.edu/people/mcdaniel/chem269/experiments/Sn2/Sn2-Reaction-lab.pdf

eport. Post-lab questions: 1. Can you predict an undesirable side reaction that might occur involving the deprotonated ethanol (sodium ethoxide)? 2. Why is it important to mix the naphthol with sodium hydroxide before adding the n-butyl iodide? What happens during this time? 3. Why does naphthol react with sodium hydroxide? Why does ethanol not react to the extent that naphthol does with sodium hydroxide? 4. What is the better nucleophile, sodium naphthoxide or naphthol? Why?

Explanation / Answer

1. yes, an undesirable side reaction would be the reaction of sodium ethoxide with butyl iodide which depends on the mode of addition leads to the product.

2. It is important to mix the naphthol with sodium hydroxide before addinng the n-butyl iodide because at this time the sodium anphthoxide is being formed which will then react with the substrate n-butyl iodide. Anychange in the mode of addition will lead to undesired product.

3. The naphthol reacts with sodium hydroxide to form the naphtyl alkoxide . The ethanol also reacts with sodium hydroxide at a faste rate due to the solubility medium issues because the naphtol and sodium hydroxide are not in a similar medium for a reaction.

4. sodium naphthoxide is a better nucleophile than naphthol, because the nucleophile adds on to the n-butyl iodide which leads to the elimination of iodide anion leading the product. The naphthol is a weakest nuceophile inn comparison to the sodium naphthoxide.

Related Questions

Navigate

• Browse (All)
• Browse T
• Subjects

---

---

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.