Question

EXPERIMENT #7c SYNTHESISs OF NEROLIN Date: Section: Name Professor EXP Ne IDATA Pr Theoretical Reaction Data OH КОН Molar mass (g/mol) Volume (mL) Density Mass (g) Mols. Quantitative Data (2-Propoxynaphthalene) Theor. Mass (g) Actual Mass (g) Percent Yield m.p. (C)-lit. m.p. (C)-actual EXPERIMENT #7: SYNTHESIS OF NEROLIN Name Professor: Date: Section: POSTLAB QUESTIONS 1. What would have been the reaction product(s) if 2-iodo-2-metthypropane was used? Draw a chemical reaction to answer this question. 2. Both 2-naphthol and methanol are alcohols with acidic protons. Explain why methanol does not react the same way in this reaction as 2-naphthol. 3. Predict the major SN2 and E2 reaction product(s) of the following reactions where appropriate. a) OH кон CH он b) OH KOH CH,он c) OH кон CHон d) OH KOH CH,он 53

Answer 1

1.

Here, 2-Iodo-2-methylpropane is tertiary alkyiodide. In presence of strong base like KOH, tertiary alkylhalides under go elimination reaction over substitution rections. So, the major product is alkene and minor product is substituted product.

OH + major E2 product

2.

The methanol is aliphatic alcohol. Its corresponding conjugate base CH3O- does not have resonance stuctures to stabilize.  But, 2- Napthol is an aromatic alcohol. Its corresponding 2-Napthoxide has several resonance structures to stabilize.

CH CH

3.

b. а. major E2 product d. c. major E2 product