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- When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observedWhen 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed.(c) Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutanea. How many s bond orbitals are available for overlap with the vacant p orbital in 1. the isobutyl cation? 2. the n-butyl cation? 3. the sec-butyl cation? b. Which of the carbocations in part a is most stable?
- 1/ For each of the molecular formulas, determine the number of elements of unsaturation and draw 3 examples: a) C6H8O2 b) C6H3NClBr 2/ Propose mechanism (showing explicity how observed mixtures of products are formed) cyclopenta-1,3-diene + Br2 ---> 3,4-dibromocyclopent-1-ene + 3,5-dibromocyclopent-1-ene 3/ Diel-Alder product of heating hexa-1,3,5-triene with maleic anhyPlease identify priorities of functional groups and name following molecules based on thier stereochemistry as R or SIn 4+2 cycloaddition, ENDO stereochemistry is preferred because: endo stereochemistry allows the diene to adopt s-cis conformation. endo stereochemistry results in less steric hindrance. the transition state leading to endo stereochemistry is higher energy. it allows for additional π to π overlap between the diene and the dienophile.
- Does cis- or trans-1-bromo-4-tert-butylcylohexane react faster in an E2reaction?Carbocations often rearrange, as shown below. Draw in the hydrogens on the two carbons involved in the rearrangement, and show formal arrow-pushing to illustrate the transformation.The hydrobrominationof 2-methyl-1-butene could theoretically lead to 2 different alkyl bromides; in practice only one product is formed. Draw the structure of both theoretical products, circle the one that is actually produced, and briefly explain whyonly one product forms.