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

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions - SOCl2 and PBr3

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions - SOCl2 and PBr3

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1:17 minutes

Problem 34b

Textbook Question

Identify the reagent that should be used to obtain each stereochemical outcome shown.
(b)

Verified step by step guidance

Step 1: Understand the stereochemical outcome desired. Determine if the reaction requires a syn or anti addition, retention or inversion of configuration, or if it involves a specific stereochemistry such as E/Z or R/S.

Step 2: Identify the type of reaction that can lead to the desired stereochemical outcome. Common reactions include hydrogenation, halogenation, hydroboration-oxidation, and epoxidation, each with specific stereochemical implications.

Step 3: Consider the starting material and its functional groups. The presence of double bonds, alcohols, or other functional groups will influence the choice of reagent.

Step 4: Select the appropriate reagent based on the reaction type and starting material. For example, syn addition might require reagents like H2 with a catalyst for hydrogenation, while anti addition might use Br2 in a halogenation reaction.

Step 5: Verify the stereochemical outcome by considering the mechanism of the reaction. Ensure that the chosen reagent will lead to the desired stereochemistry by analyzing the transition states and intermediates involved.

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Key Concepts

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

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and its impact on chemical reactions. Understanding stereochemistry is crucial for predicting the outcome of reactions, especially when different stereoisomers can form. It includes concepts like chirality, enantiomers, and diastereomers, which are essential for determining the stereochemical outcome of a reaction.

Reagents and Reaction Mechanisms

Reagents are substances used to cause a chemical reaction, and understanding their role is key to predicting reaction outcomes. Different reagents can lead to different stereochemical configurations by influencing the reaction mechanism, such as nucleophilic substitution or elimination. Knowing the specific reagents and their effects on molecular structure helps in selecting the right one for desired stereochemical results.

Stereoselective Reactions

Stereoselective reactions are those where a particular stereoisomer is preferentially formed over others. These reactions are influenced by the choice of reagents and conditions, which can favor the formation of one stereoisomer due to factors like steric hindrance or electronic effects. Understanding how to control these reactions is essential for achieving specific stereochemical outcomes in synthesis.

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Related Practice

Textbook Question

Provide the alcohol that would be used to make the bromoalkanes shown using PBr₃.

(b)

Textbook Question

Provide the alcohol that would be used to make the bromoalkanes shown using PBr₃.

(c)

Textbook Question

Besides PBr₃. and SOCl₂ , there are other ways of synthesizing haloalkanes. One such way is shown. Provide an arrow-pushing mechanism that rationalizes formation of the chloroalkane. [Hint: Dimethyl sulfide is a good nucleophile and Cl₂ is an electrophile. Start by reacting those two together.]

Textbook Question

Identify the reagent that should be used to obtain each stereochemical outcome shown.

(a)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃. If no reaction occurs, write 'no reaction.'

(a)

Textbook Question

Suggest the appropriate reagents to carry out the following transformations.

(g)

Textbook Question

Draw structures for compounds A–F.

Textbook Question

What is the product of each of the following reactions?

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