Ch. 8 - Elimination ReactionsWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Solution: 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

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.