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(a)
Interpretation:
It should be identified that will a thermal 1, 3-migrations of carbon occur with whether retention or inversion of configuration.
Concept introduction:
Pericyclic reactions are “ any concerted reaction in which bonds are formed or brocken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.
There are mainly three types of pericyclic reactions,
- 1) Electrocyclic reactions
- 2) Cycloaddition reactions
- 3) Sigmatropic reactions
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
Inversion of configuration is the inversion of a chiral center in a molecule in a
Retention of configuration is the preservation of integrity of the spatial arrangement of bonds to a chiral center during a chemical reaction.
(b)
Interpretation:
It should be identified that will a thermal 1, 5-migrations of carbon occur with whether retention or inversion of configuration.
Concept introduction:
Pericyclic reactions are “ any concerted reaction in which bonds are formed or brocken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.
There are mainly three types of pericyclic reactions,
- 1) Electrocyclic reactions
- 2) Cycloaddition reactions
- 3) Sigmatropic reactions
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
Inversion of configuration is the inversion of a chiral center in a molecule in a chemical reaction.
Retention of configuration is the preservation of integrity of the spatial arrangement of bonds to a chiral center during a chemical reaction.
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Chapter 28 Solutions
Organic Chemistry; Organic Chemistry Study Guide A Format: Kit/package/shrinkwrap
- Identify the missing organic reactants in the following reaction: X + Y H+ two steps Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H2O) are not shown. In the drawing area below, draw the skeletal ("line") structures of the missing organic reactants X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. Х :arrow_forwardDraw the mechanism of friedel-crafts acylation using acetyl chloride of m-Xylenearrow_forwardI need help naming these in IUPACarrow_forward
- H R Part: 1/2 :CI: is a/an electrophile Part 2 of 2 Draw the skeletal structure of the product(s) for the Lewis acid-base reaction. Include lone pairs and formal charges (if applicable) on the structures. 4-7: H ö- H Skip Part Check X :C1: $ % L Fi Click and drag to start drawing a structure. MacBook Pro & ㅁ x G 0: P Add or increase positive formal cha Save For Later Submit ©2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Centearrow_forwardDraw the friedel-crafts acylation mechanism of m-Xylenearrow_forwardDon't used hand raiting and don't used Ai solutionarrow_forward
- 1. Base on this experimental results, how do you know that the product which you are turning in is methyl 3-nitrobenzoate(meta substituted product ) rather than either of the other two products? 2. What observation suggests that at least a small amount of one or both of the other two isomers are in the mother liquor?arrow_forwardExplain Huckel's rule.arrow_forwardhere is my question can u help me please!arrow_forward
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENTPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
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