E2 - Cumulative Practice Video Lessons

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Problem: When (3R, 4S)-4-bromo-3-methylheptane is treated with strong base, such as potassium tert-butoxide in tert-butanol at 100 °C an elimination reaction takes place and produces one major product and two minor products. A. Draw the correct structure for the starting material.     B. Draw the structure of the thermodynamically-favored major product.     C. Draw the structures of two kinetically-favored minor products.     D. The formation of the thermodynamic product occurs through a stereoselective mechanism. In 1-2 sentences explain why this mechanism is stereoselective.     E. One of the minor products is formed in higher yield than the other minor product. In 1-2 sentences explain why this minor product is formed in higher yield in terms of the relative thermodynamic stability of the two products. You must adequately account for the different factors that affect stability.    

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Problem Details

When (3R, 4S)-4-bromo-3-methylheptane is treated with strong base, such as potassium tert-butoxide in tert-butanol at 100 °C an elimination reaction takes place and produces one major product and two minor products.

A. Draw the correct structure for the starting material.

B. Draw the structure of the thermodynamically-favored major product.

C. Draw the structures of two kinetically-favored minor products.

D. The formation of the thermodynamic product occurs through a stereoselective mechanism. In 1-2 sentences explain why this mechanism is stereoselective.

E. One of the minor products is formed in higher yield than the other minor product. In 1-2 sentences explain why this minor product is formed in higher yield in terms of the relative thermodynamic stability of the two products. You must adequately account for the different factors that affect stability.

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