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

Previous problemNext problem

1:21 minutes

Problem 34a

Textbook Question

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

Verified step by step guidance

Step 1: Begin by analyzing the stereochemical outcome desired in the reaction. Determine if the reaction requires a specific stereochemistry, such as syn or anti addition, or if it involves the formation of a chiral center.

Step 2: Consider the type of reaction mechanism that will lead to the desired stereochemical outcome. Common mechanisms include SN1, SN2, E1, E2, and addition reactions. Each mechanism has distinct stereochemical implications.

Step 3: Identify the functional groups present in the starting material and the product. This will help in selecting the appropriate reagent that can facilitate the transformation while maintaining or altering stereochemistry as needed.

Step 4: Evaluate the reagents that are known to influence stereochemistry. For example, reagents like Lindlar's catalyst can lead to syn addition, while reagents like sodium or lithium in liquid ammonia can lead to anti addition.

Step 5: Choose the reagent that matches the desired stereochemical outcome based on the analysis of the mechanism and functional groups. Ensure that the reagent is compatible with the substrate and will not lead to undesired side reactions.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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 how this affects their chemical behavior. Understanding stereochemistry is crucial for predicting the outcomes of reactions, especially when it comes to the formation of chiral centers and the resulting stereoisomers, such as enantiomers and diastereomers.

Reagents and Reaction Conditions

Reagents are substances or compounds added to a system to cause a chemical reaction or test if a reaction occurs. The choice of reagent and reaction conditions (such as temperature, solvent, and time) can significantly influence the stereochemical outcome of a reaction, determining whether a product is formed as a specific stereoisomer.

Mechanism of Reaction

The mechanism of a reaction describes the step-by-step process by which reactants are transformed into products. Understanding the mechanism is essential for predicting stereochemical outcomes, as it reveals how different reagents interact with substrates, the intermediates formed, and how these factors influence the stereochemistry of the final product.

Watch next

Master Learning the mechanism of SOCl2. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

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

(a)

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.

(b)

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.

Show more practices