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

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4:21 minutes

Problem 88

Textbook Question

Of the possible products shown for the following reaction, are there any that will not be formed?

Verified step by step guidance

Step 1: Analyze the given reactants and reaction conditions. The reactants are 1-bromo-2-propene (CH3-CH=CH2-Br) and HCl. This reaction involves electrophilic addition of HCl to the double bond in the alkene.

Step 2: Recall Markovnikov's rule, which states that in the addition of HX (where X is a halogen) to an alkene, the hydrogen atom will add to the carbon with more hydrogen atoms already attached, and the halogen will add to the carbon with fewer hydrogen atoms.

Step 3: Identify the possible carbocation intermediates. When HCl adds to the double bond, the proton (H⁺) can add to either the terminal carbon (CH2) or the middle carbon (CH) of the double bond, forming two possible carbocations: a primary carbocation (less stable) or a secondary carbocation (more stable). The secondary carbocation is favored due to its greater stability.

Step 4: Predict the major product based on the favored carbocation intermediate. The Cl⁻ ion will attack the more stable secondary carbocation, leading to the formation of the Markovnikov product. The anti-Markovnikov product is unlikely under these conditions unless a peroxide is present, which is not indicated here.

Step 5: Evaluate the given products. The product where Cl is attached to the terminal carbon (anti-Markovnikov product) will not be formed under these conditions. The other products shown are consistent with Markovnikov addition and are plausible.

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the role of catalysts. By analyzing the mechanism, one can predict which products are likely to form and which are not based on the stability of intermediates and the energy barriers involved.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. This concept is essential for predicting the outcome of reactions, especially in cases where functional groups can react at different positions on a molecule. Understanding regioselectivity helps in determining which products will be favored based on the stability of the resulting isomers.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions that can produce stereoisomers, it is important to consider factors such as chirality and stereoselectivity. Recognizing how stereochemical factors influence product formation is key to understanding which products may or may not be formed in a given reaction.

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