Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

10. Addition Reactions

Dihydroxylation

Organic Chemistry

10. Addition Reactions

Dihydroxylation

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1:09 minutes

Problem 7d

Textbook Question

We have studied a number of pericyclic reactions previously. Draw the mechanism of the steps shown. The section number where this material was first studied is given for your review.
(d)

Verified step by step guidance

Step 1: Begin by identifying the type of pericyclic reaction involved. Pericyclic reactions include cycloadditions, electrocyclic reactions, sigmatropic rearrangements, and cheletropic reactions. Determine which category the given reaction falls into based on the structural changes in the reactants and products.

Step 2: Analyze the electron movement in the reaction. Pericyclic reactions typically proceed through a concerted mechanism, meaning all bond-making and bond-breaking events occur simultaneously. Use curved arrows to show the flow of electrons during the reaction.

Step 3: Consider the stereochemical implications of the reaction. Pericyclic reactions often follow specific stereochemical rules, such as the Woodward-Hoffmann rules, which depend on the symmetry of the molecular orbitals involved. Determine whether the reaction is thermally or photochemically driven, as this affects the stereochemical outcome.

Step 4: Draw the transition state of the reaction. The transition state is cyclic and involves the overlap of π orbitals. Represent the cyclic structure and the electron movement clearly to illustrate how the reactants transform into the products.

Step 5: Finally, complete the mechanism by showing the final product(s) formed. Ensure that all bonds are correctly represented, and verify that the electron count and stereochemistry align with the rules governing pericyclic reactions.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Pericyclic Reactions

Pericyclic reactions are a class of organic reactions that occur through a concerted mechanism, involving the cyclic rearrangement of electrons. These reactions typically involve the overlap of orbitals in a cyclic transition state, leading to the formation of new bonds without the need for intermediates. Common types include cycloadditions, electrocyclic reactions, and sigmatropic rearrangements, each governed by specific selection rules.

Mechanism of Reactions

The mechanism of a reaction describes the step-by-step process by which reactants are converted into products. It includes the identification of intermediates, transition states, and the movement of electrons, often illustrated using curved arrows. Understanding the mechanism is crucial for predicting the outcome of reactions and for designing synthetic pathways in organic chemistry.

Orbital Overlap

Orbital overlap is a fundamental concept in chemistry that refers to the interaction between atomic orbitals when forming chemical bonds. In pericyclic reactions, the overlap of p-orbitals is essential for the concerted movement of electrons, allowing for the formation of new sigma bonds while breaking pi bonds. This concept is key to understanding the stereochemistry and regioselectivity of pericyclic processes.

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Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(n)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iv) 1. OsO₄ 2. NaHSO₃. If there is no reaction, write 'no reaction.'

(a)

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Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(b)

Textbook Question

Predict the product of each of the following alcohol synthesis reactions.

(d)

Textbook Question

Draw the structure of and name the enantiomeric diols that result from the cis-dihydroxylation of the alkene shown.

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃

(l)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃

(f)

Textbook Question

Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?

(c)

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We have studied a number of pericyclic reactions previously. Draw the mechanism of the steps shown. The section number where this material was first studied is given for your review. (d)

Key Concepts

Pericyclic Reactions

Mechanism of Reactions

Orbital Overlap

Watch next

We have studied a number of pericyclic reactions previously. Draw the mechanism of the steps shown. The section number where this material was first studied is given for your review.
(d)