Solution: The reaction between compound 1 and NaOCHMe2 in Me2CHOH as a solvent produces a mixture of two products 2 and 3, all with identical molecular formula and with a relative yield of 50% and 50% respectively. The 1NMR of these compounds with relative integrations of signals is shown below. What are the structures of compounds 2 and 3? b. With what reagent and solvent would you treat compound 1 if you want to obtain higher yield of compound 2? Explain your answer with 1-2 sentences c.  With what reagent and solvent would you treat compound 1 if you want to obtain higher yield of compound 3? Explain your answer with 1-2 sentences d.  Based on the data above, what product(s) and in what relative ratio(s) would you obtain by treating compound 4 ((t-But)2CHCH(Br)CH3) with NaOCHMe2 in Me2CHOH as the solvent under the same conditions as above? Explain your answer with 1-2 sentences.

Problem

The reaction between compound 1 and NaOCHMe2 in Me2CHOH as a solvent produces a mixture of two products 2 and 3, all with identical molecular formula and with a relative yield of 50% and 50% respectively. The 1NMR of these compounds with relative integrations of signals is shown below. What are the structures of compounds 2 and 3?

b. With what reagent and solvent would you treat compound 1 if you want to obtain higher yield of compound 2? Explain your answer with 1-2 sentences

c.  With what reagent and solvent would you treat compound 1 if you want to obtain higher yield of compound 3? Explain your answer with 1-2 sentences

d.  Based on the data above, what product(s) and in what relative ratio(s) would you obtain by treating compound 4 ((t-But)2CHCH(Br)CH3) with NaOCHMe2 in Me2CHOH as the solvent under the same conditions as above? Explain your answer with 1-2 sentences.