2

At a different institution the effect of alkane and base structure was studied to determine if substitution

Question

2. At a different institution the effect of alkane and base structure was studied to determine if substitution

or elimination was favored. Among the various systems examined, 2-bromo-2-methylbutane was used as the starting material and sodium methoxide as base and the product distribution was determined using gas chromatography. THIS ARTICLE IS ATTACHED

a. Compare the reaction conditions used in our elimination experiment vs. the conditions used in the article using the same starting material and sodium methoxide as the base.

in our reaction we used KOH and tert butoxide as the bases, with 2-bromo-2-methylbutane

b. What was the distribution of substitution vs. elimination in their product in the above reaction?

c. In our experiment, the elimination product was favored. However, would not be able to see any substitution product formed in our reaction. Why was that the case?

d. If we were to run kinetic experiments on our reaction with KOH as well as the one in the article with the methoxide and 2-methyl-2-bromobutane, which would give a higher rate (faster)? Show your answer.

3. The following amines are sometimes used as bases for elimination reactions: N,N-diisopropylethylamine (DIPEA), 1,8-diazabicycloundec-7-ene (DBU), 2,6-di-tert-butylpyridine. Perform a literature search and provide the structure of these bases. What do they all have in common that makes them good bases for elimination as oppose to dimethylamine? Explain your answer.

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