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

Hydrohalogenation

Organic Chemistry

10. Addition Reactions

Hydrohalogenation

Previous problemNext problem

3:00 minutes

Problem 32

Textbook Question

Provide an arrow-pushing mechanism that rationalizes the formation of each of the products you predicted in Assessment 8.31. Make sure your mechanism accounts for all products formed, including stereoisomers and regioisomers, where applicable.

Verified step by step guidance

Identify the starting materials and the type of reaction taking place. Consider the functional groups involved and the reagents used in Assessment 8.31.

Determine the possible intermediates that can form during the reaction. Use your knowledge of reaction mechanisms to predict how electrons will move. This often involves identifying nucleophiles and electrophiles.

Draw the arrow-pushing mechanism for the formation of the first product. Start by showing the movement of electrons from the nucleophile to the electrophile, forming new bonds or breaking existing ones.

Consider stereochemistry and regioselectivity. For each product, analyze how the arrangement of atoms might lead to different stereoisomers or regioisomers. Use wedge and dash notation to indicate stereochemistry where applicable.

Repeat the arrow-pushing mechanism for each additional product, ensuring that all possible stereoisomers and regioisomers are accounted for. Compare the stability of each product to rationalize their formation.

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.

Arrow-Pushing Mechanism

Arrow-pushing is a technique used in organic chemistry to depict the movement of electrons during chemical reactions. It involves using curved arrows to show how electron pairs move from nucleophiles to electrophiles, helping to visualize the step-by-step transformation of reactants into products. Understanding this concept is crucial for predicting reaction outcomes and mechanisms.

Stereoisomers

Stereoisomers are molecules with the same molecular formula and sequence of bonded atoms, but differ in the three-dimensional orientations of their atoms. This concept is essential for understanding how different spatial arrangements can lead to distinct chemical properties and reactivities, which must be considered when predicting products in a chemical reaction.

Regioisomers

Regioisomers are isomers that differ in the position of substituents or functional groups within a molecule. This concept is important for understanding how different positions can affect the stability and reactivity of molecules, influencing the formation of specific products in a chemical reaction. Recognizing regioisomer formation is key to accurately predicting reaction outcomes.

Previous problemNext problem

4:07m

Watch next

Master General properties of hydrohalogenation. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Provide a mechanism for the following reactions occurring with rearrangement.

(b)

Textbook Question

Using an excess of HCl in the following reaction resulted in a product that was not simply the substitution of chlorine for the hydroxyl group. Predict the identity of the product obtained.

Textbook Question

Provide an arrow-pushing mechanism that rationalizes the formation of each alkyl halide in Assessment 8.19.

Textbook Question

Suggest an alkene that, upon reaction with the appropriate hydrohalic acid, will produce only the alkyl halide shown. [Ignore stereochemistry.]

(d)

Textbook Question

The following reaction gives two different constitutional isomers in nearly equal yields. Why doesn't this reaction produce only one product?

Textbook Question

Which of the following alkenes would you expect to react fastest with HBr in each pair?

(b)

Textbook Question

A wayward chemist proposed the following mechanism for the addition of HBr to an alkene.

(a) Why is this mechanism unlikely?

(b) Compare the reaction coordinate diagrams for the actual mechanism studied in Section 8.3.1 and this alternate mechanism on the same graph.

Textbook Question

What is the expected product for the reaction of each of the following alkenes with (i) HBr and (ii) HCl?

(e)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap