
Concept explainers
Interpretation:
It should be determined that the given [1, 7] sigmatropic rearrangement involves whether suprafacial or antarafacial rearrangement.
Concept introduction:
In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”
Sigmatropic rearrangement reactions are named with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.
Migration of carbon and hydrogen will occur in a sigmatropic rearrangement reaction.
When hydrogen migrates in a sigmatropic rearrangement, the s orbital of the hydrogen is partially bonded to both the migration origin and the migration terminus in the transition state.
Migration of hydrogen in suprafacial and antarafacial rearrangement can be represented as follows,
Migration of carbon occurs through two ways because it has a two lobed p orbital. Carbon can simultaneously interact with the migration origin and the migration terminus using one lobe of its p orbital. Migration of carbon in suprafacial and antarafacial rearrangement can be represented as follows,
Carbon migrating with one lobe of its p orbital interacting
Carbon migrating with both lobe of its p orbital interacting

Trending nowThis is a popular solution!

Chapter 28 Solutions
Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)
- Would the following organic synthesis occur in one step? Add any missing products, required catalysts, inorganic reagents, and other important conditions. Please include a detailed explanation and drawings showing how the reaction may occur in one step.arrow_forward(a) Sketch the 'H NMR of the following chemical including the approximate chemical shifts, the multiplicity (splitting) of all signals and the integration (b) How many signals would you expect in the 13C NMR? CH3arrow_forwardDraw the Show the major and minor product(s) for the following reaction mechanisms for both reactions and show all resonance structures for any Explain why the major product is favoured? intermediates H-Brarrow_forward
- 3. Draw ALL THE POSSBILE PRODUCTS AND THE MECHANISMS WITH ALL RESONANCE STRUCTURES. Explain using the resonance structures why the major product(s) are formed over the minor product(s). H₂SO4, HONO CHarrow_forward7. Provide the product(s), starting material(s) and/or condition(s) required for the No mechanisms required. below reaction HO + H-I CI FO Br2, FeBr3 O I-Oarrow_forward6. Design the most efficient synthesis of the following product starting from phenot Provide the reaction conditions for each step (more than one step is required) and explain the selectivity of each reaction. NO MECHANISMS ARE REQUIRED. OH step(s) CIarrow_forward
- What is the skeletal structure of the product of the following organic reaction?arrow_forwardIf a reaction occurs, what would be the major products? Please include a detailed explanation as well as a drawing showing how the reaction occurs and what the final product is.arrow_forwardWhat is the major organic product of the following nucleophilic acyl substitution reaction of an acid chloride below?arrow_forward
