Treatment of an alkyl halide with AgNO 3 in alcohol often promotes ionization. Ag + + R–Cl → AgCl + R + When 4-chloro-2-methylhex-2-ene reacts with AgNO 3 in ethanol, two isomeric ethers are formed. Suggest structures, and propose a mechanism for their formation

Hi everyone. Nuclear Felix substitution reactions of L kill. Hey lights are often facilitated by silver nitrate. When four quarrel to mess up into in react with silver nitrate and Massimo, the reaction yields two different easter products draw a mechanism that accounts for the formation of both ethers. Now, before we begin, let's just concentrate on our substrate. For chlor oh two method bend to in to draw it. We wish to draw a five member chain. So we have fencing. So that'd be five carbons in a chain between carbons. Number two and three we have a two in which means a double bond. Position. Number two also has a muscle group and position number four has a chloral substitution. So that's how we get the structure of our substrate. Now, let's think about the role of silver nitrate recall from general chemistry that all nitrates are soluble and that means that in a solution, silver nitrate associates into silver can ions and nitrate and ions. And generally because nitrate and islands are famous for being and Spectators were primarily interested in the role of silver in this reaction. Silver career ions in particular have an affinity to intelligence because of the possible formation of insoluble chlorides or Hey lights, What that means is that the original electrons in the carbon chlorine bond are placed into the d orbital of silver promoting the formation of the carbo carry on. So the first step in this mechanism is the loss of the leaving group or the formation of the carb. Okay, Ryan having removed chlorine, we form our carbo cast iron which is a secondary carbo cast iron, but it's also resident stabilized because there are adjacent pi electrons. Now this means that we may now draw that resonant structure that we obtained after shifting the pi electrons towards the car broken iron. So the original second rate card book at iron undergoes residents to form a tertiary carbo cast iron. So these two our our our resonance structures notice that, as we previously stated, this is the tertiary carbo cast iron. And now the reaction takes place in a methanol. Methanol by itself is a molecular nuclear file, meaning it's a solis reaction. Now it's an S. N. One reaction because it's a weak nuclear file, it doesn't contain any charge. And therefore this nuclear file might attack any of the two resonance forms minimal. Can attack the first carbo Karen. So we will have the nuclear attack step over here attacking the first carbo Karen over here or that exactly the same molecule could also attack a tertiary carbo Karen. So both of these are the nuclear attack steps. And our oldest we have to do is simply draw their results and products. Now after we bond muscle to that first carbo Karen, which was the secondary carbo Karen, oxygen forms a bond to carbon and we have the protein ated form or the protein ated intermediate and oxygen contains a form of positive charge. Similarly, this is what we expect to see for the next structure. We will form a protein ated intermediate at a different position. Again, oxygen here has a formal positive charge because it forms three different bonds. Our final step is the D. Protein Nation step. We we do not necessarily have to worry showing the actual base that acts in this deep rotation stop. We may simply say that it could be chloride, or it could be another molecule of methanol, but we can use the shorthand notation and simply state that we're D protein. Ating that protein, it'd intermediate in each case. And we are forming our final products. Now these our our final products and this is the overall mechanism for this reaction. The correct multiple choice answer for this question is B And if you have any questions, feel free to leave them down below. Thank you for watching this video.

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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

7. Substitution Reactions

SN1 Reaction

Organic Chemistry

7. Substitution Reactions

SN1 Reaction

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6:21 minutes

Problem 6

Textbook Question

Treatment of an alkyl halide with AgNO₃ in alcohol often promotes ionization.
Ag⁺ + R–Cl → AgCl + R⁺
When 4-chloro-2-methylhex-2-ene reacts with AgNO₃ in ethanol, two isomeric ethers are formed. Suggest structures, and propose a mechanism for their formation

Verified step by step guidance

Step 1: Recognize the reaction type. The reaction involves the ionization of the alkyl halide (4-chloro-2-methylhex-2-ene) in the presence of AgNO3 in ethanol. The Ag+ ion promotes the formation of a carbocation by abstracting the chloride ion (Cl⁻), leaving behind a positively charged carbocation (R⁺).

Step 2: Analyze the carbocation intermediate. The initial carbocation formed is a secondary carbocation at the 4th carbon (C-4). However, carbocations can undergo rearrangements to form more stable carbocations. In this case, a hydride shift from the adjacent C-3 carbon can occur, leading to a more stable tertiary carbocation at C-3.

Step 3: Consider the nucleophilic attack. Ethanol (CH₃CH₂OH), acting as a nucleophile, can attack the carbocation. The nucleophilic attack can occur at either the secondary carbocation (if no rearrangement occurs) or the tertiary carbocation (after rearrangement). This results in the formation of two different ethers.

Step 4: Propose the structures of the ethers. If ethanol attacks the secondary carbocation (C-4), the product will be 4-ethoxy-2-methylhex-2-ene. If ethanol attacks the tertiary carbocation (C-3), the product will be 3-ethoxy-2-methylhex-2-ene.

Step 5: Summarize the mechanism. The reaction proceeds via ionization of the alkyl halide to form a carbocation, followed by a possible hydride shift to form a more stable carbocation. Ethanol then acts as a nucleophile, attacking the carbocation to form the two isomeric ethers: 4-ethoxy-2-methylhex-2-ene and 3-ethoxy-2-methylhex-2-ene.

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Key Concepts

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

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (F, Cl, Br, I). They are important in organic chemistry as they can undergo various reactions, including nucleophilic substitution and elimination. The reactivity of alkyl halides is influenced by the structure of the carbon chain and the nature of the halogen, which affects the stability of the resulting carbocation during ionization.

Nucleophilic Substitution Mechanism

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the case of alkyl halides, the reaction can proceed via either an SN1 or SN2 mechanism. The SN1 mechanism involves the formation of a carbocation intermediate, while the SN2 mechanism involves a direct attack by the nucleophile, leading to a concerted reaction. The choice of mechanism depends on factors such as substrate structure and solvent.

Isomerism in Ethers

Isomerism refers to the existence of compounds with the same molecular formula but different structural arrangements. In the context of ethers formed from the reaction of 4-chloro-2-methylhex-2-ene with AgNO3 in ethanol, two isomeric ethers can arise from different arrangements of the alkyl groups around the ether oxygen. Understanding the formation of these isomers requires knowledge of the reaction conditions and the stability of potential carbocation intermediates.

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