At a different institution the effect of alkane and base structure was studied t

Question

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. Perform a literature search using the web of science to find the article. Answer the following questions regarding that particular reaction (described above) from the article. Attach the first page of the article to your lab report. 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. 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. What parameter in the reaction conditions used in our lab vs. the one in the article shifted the product in favor of elimination? d. Dr. Koppel hypothesized that if kinetic experiments were run on our reaction as well as the one in the article, our reaction would give a higher rate (faster). Would you

Explanation / Answer

a. The conditions used are elimination conditions. Sodium methoxide is a strong base therefore it promotes elimination. Tertiary alkyl halide is bulky and has a lot of steric hinderance

b. Distribution wil be predominantly by the eliminated product.. sodium methoxide act as a strong base and also a strong nucleophile.but the bacisity plus the subtrate being a tertiary alkyl halide promotes E2 pathway.

C. The stronger base and the steric hinderance of the alkyl halide.

d. Yes. Reaction when run under kinetic control gives a higher yeild.

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