Interpretation:
Thermal electrocyclic ring closure of (2Z, 4Z, 6Z)-2,4,6-octatriene yielding products via conrotatory and disrotatory cyclizations.
Concept introduction:
Conrotatory and disrotatory is based on the rotation at each end of the molecule. In conrotatory mode, both atomic orbitals of the end groups turn in the same direction ,such as both atomic orbitals rotating clockwise or counter-clockwise. In disrotatory mode, the atomic orbitals of the end groups turn in opposite directions ,one atomic orbital turns clockwise and the other counter-clockwise. The cis/trans geometry of the final product is directly decided by the difference between conrotation and disrotation.
Whether a particular reaction is conrotatory or disrotatory can be accomplished by examining the molecular orbitals of each molecule and through a set of rules. Only two pieces of information are required to determine conrotation or disrotation using the set of rules: how many electrons are in the pi-system and whether the reaction is induced by heat or by light. This set of rules can also be derived from an analysis of the molecular orbitals for predicting the stereochemistry of electrocyclic reactions.
Trending nowThis is a popular solution!
Chapter 30 Solutions
Organic Chemistry
- Predict the major products of the following reactions. Include stereochemistry whereapplicable.(a) 1@methylcycloheptene + BH3 # THF, then H2O2, OH-(b) trans@4,4@dimethylpent@2@ene + BH3 # THF, then H2O2, OHarrow_forwardThe reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs due to a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain what this observation tells about the mechanism of the reaction.arrow_forwardThe isomer of 1,2,3,4,5,6-hexachlorocyclohexane shown undergoes E2 elimination 7000 times more slowly than any of its steroisomers. Explain this observation.arrow_forward
- Give all the monobromination products of 2-methylpropane (or isobutane) in presence of heat or energy. Identify the major product and propose a mechanism leading to the formation of the major product. Provide a reaction in the termination step.arrow_forward(a) Give a mechanism for this reaction, showing how the two products arise as aconsequence of the resonance-stabilized intermediate.(b) The bromination of cyclohexene using NBS gives only one major product, as shown onthe previous page. Explain why there is no second product from an allylic shift.arrow_forwardAlthough there are nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane, one stereoisomer reacts 7000 times more slowly than any of the others in an E2 elimination. Draw the structure of this isomer and explain why this is so.arrow_forward
- Propose mechanisms and draw reaction-energy diagrams for the following reactions. Pay particular attention to the structures of any transition states and intermediates. Compare the reaction-energy diagrams for the two reactions, and explainthe differences.(a) 2-Bromo-2-methylbutane reacts with sodium methoxide in methanol to give 2-methylbut-2-ene (among other products)arrow_forwardConsider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide. Deduce the mechanism of this reaction working step by step. Write all possible products showing the stereochemistry.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning