
(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-W/S.G+SOLN.MANUAL
- Draw the Markovnikov product of the hydrobromination of this alkene. Note for advanced students: draw only one product, and don't worry about showing any stereochemistry. Drawing dash and wedge bonds has been disabled for this problem. + Explanation Check 1 X E 4 1 1 1 1 1 HBr Click and drag to start drawing a structure. 80 LE #3 @ 2 $4 0 I அ2 % 85 F * K M ? BH 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center & 6 27 FG F10 8 9 R T Y U D F G H P J K L Z X C V B N M Q W A S H option command H command optiarrow_forwardBe sure to use wedge and dash bonds to show the stereochemistry of the products when it's important, for example to distinguish between two different major products. Predict the major products of the following reaction. Explanation Q F1 A Check F2 @ 2 # 3 + X 80 F3 W E S D $ 4 I O H. H₂ 2 R Pt % 05 LL ee F6 F5 T <6 G Click and drag to start drawing a structure. 27 & A 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center Acce Y U H DII 8 9 F10 4 J K L Z X C V B N M T H option command F11 P H commandarrow_forwardCurved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the arrows to draw the intermediate and product in this reaction or mechanistic step(s). Include all lone pairs and charges as appropriate. Ignore stereochemistry. Ignore inorganic byproducts. H :0: CH3 O: OH Q CH3OH2+ Draw Intermediate protonation CH3OH CH3OH nucleophilic addition H Draw Intermediate deprotonation :0: H3C CH3OH2* protonation H 0: H CH3 H.arrow_forward
- Predicting the reactants or products of hemiacetal and acetal formation uentify the missing organic reactants in the following reaction: H+ X+Y OH H+ за 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. Explanation Check Click and drag to start drawing a structure. ? olo 18 Ar © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibilityarrow_forwardcan someone please answer thisarrow_forwardPlease, please help me figure out the the moles, molarity and Ksp column. Step by step details because I've came up with about three different number and have no idea what I'm doing wrong.arrow_forward
- In this question, the product of the aldol condensation is shown. What would be the reactants for this product? Please provide a detailed explanation, as well as a drawing showing how the reactants will react to produce the product.arrow_forward7. Propene undergoes a hydration reaction with water in the presence of an acid. a. There are two possible products for this reaction, both with the formula C,H,O. Show their structural formulas and names. (A1, B2) SCH4UR Name: (answer for part a. here!) VER 3 2021-2022 b. Which of the two products do you predict will form. Explain your choice using details from your learning. (B3)arrow_forwardWhat are the major products of the following organic reaction? Please include a detailed explanation as well as a drawing as to how the reaction proceeds.arrow_forward
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