Interpretation:
Whether the reaction shown will take place in conrotatory or disrotatory manner is to be stated. The stereochemistry of the cyclobutene product is to be given and explained.
Concept introduction:
An electrocyclic reaction involves the cyclization of a conjugated acyclic system. These reactions are reversible and are highly stereospecific.
In elecrocyclic reactions involving even number of electron pairs, a thermal reaction occurs in conrotatory manner and a photochemical reaction occurs in disrotatory manner.
In elecrocyclic reactions involving odd number of electron pairs, a thermal reaction occurs in disrotatory manner and a photochemical reaction occurs in conrotatory manner.
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Chapter 30 Solutions
Organic Chemistry
- Predict the major product or provide the reagents in the following reactions . Be sure to show stereochemistry if necessary.arrow_forwardComplete the following reactions. Show all possible products and indicate stereochemistry where appropriate.arrow_forwardWrite the mechanisms of the following reactions and examine the products as stereoisomeric.arrow_forward
- Predict the products of the following reactions, showing stereochemistry where appropriate.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_forwardPropose a plausible mechanism for the 1 to 2 conversion as shown, and explain the stereochemical result:arrow_forward
- In a strongly acidic solution, cyclohexa-1,4-diene tautomerizes to cyclohexa-1,3-diene.Propose a mechanism for this rearrangement, and explain why it is energetically favorablearrow_forwardComplete the following reactions by providing the missing product(s). Determine what mechanism operates in each case (SN1, SN2, E1, or E2). Show the stereochemistry of the product(s) where appropriate. If more than one product is formed circle the major one.arrow_forwardPredict the product and give the stereochemistry resulting from reaction of each of the followingnucleophiles with (R)-2-bromooctanearrow_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_forwardShow how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclicreagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.(a) 1-phenyl-1-bromobutanearrow_forwardPredict the major products of the following reactions, including stereochemistry where appropriate. (S)-2-butyl tosylate + NaBrarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning