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

7. Substitution Reactions

SN1 Reaction

Organic Chemistry

7. Substitution Reactions

SN1 Reaction

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4:03 minutes

Problem 12a

Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following S_N1 reactions.
(a)

Verified step by step guidance

Step 1: Identify the substrate in the Sₙ1 reaction. The Sₙ1 mechanism typically involves a tertiary or secondary alkyl halide as the substrate, which can form a stable carbocation intermediate.

Step 2: Recognize the first step of the Sₙ1 mechanism, which is the loss of the leaving group. The leaving group departs, forming a carbocation intermediate. Represent this step using curved arrows to show the movement of electrons from the bond to the leaving group.

Step 3: Analyze the stability of the carbocation intermediate. If the carbocation can undergo rearrangement (e.g., hydride shift or alkyl shift) to form a more stable carbocation, include this step in the mechanism.

Step 4: Identify the nucleophile in the reaction. The nucleophile attacks the carbocation, forming a new bond. Use curved arrows to show the movement of electrons from the nucleophile to the carbocation.

Step 5: If necessary, include a proton transfer step to complete the reaction. For example, if the nucleophile is neutral, it may need to lose a proton to form the final product. Represent this step with curved arrows showing the movement of electrons.

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Key Concepts

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

Sₙ1 Mechanism

The Sₙ1 (substitution nucleophilic unimolecular) mechanism involves a two-step process where the leaving group departs first, forming a carbocation intermediate. This is followed by the nucleophile attacking the carbocation. The rate of the reaction depends only on the concentration of the substrate, making it a unimolecular process. Understanding this mechanism is crucial for predicting the behavior of substrates in nucleophilic substitution reactions.

Carbocation Stability

Carbocations are positively charged species that play a central role in Sₙ1 reactions. Their stability is influenced by factors such as the degree of substitution (primary, secondary, tertiary) and resonance. Tertiary carbocations are the most stable due to hyperconjugation and inductive effects from surrounding alkyl groups. Recognizing the stability of carbocations helps in predicting the feasibility and rate of Sₙ1 reactions.

Nucleophiles

Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. In Sₙ1 reactions, the nucleophile attacks the carbocation after the leaving group has departed. The strength and nature of the nucleophile can significantly affect the reaction rate and outcome. Common nucleophiles include water, alcohols, and halides, and understanding their reactivity is essential for drawing accurate reaction mechanisms.

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Related Practice

Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following S_N1 reactions.

(b)

Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following S_N1 reactions.

(c)

Textbook Question

Provide a mechanism for the following S_N1 reactions that feature a rearrangement.

(a)

Textbook Question

Which of the following S_N1 reactions should proceed at a faster rate? Justify your answer on a reaction coordinate diagram.

Textbook Question

The allylic bromide below gives two S_N1 products. Justify the formation of each.

Textbook Question

Rank the ability of the following compounds to undergo an S_N1 reaction ( 1 = fastest, 5 = slowest ).

Textbook Question

Propose a mechanism for each reaction, showing explicitly how the observed mixtures of products are formed.

(b) 2-methylbut-3-en-2-ol + HBr → 1-bromo-3-methylbut-2-ene + 3-bromo-3-methylbut-1-ene

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

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Practice your electron-pushing skills by drawing a mechanism for the following SN1 reactions.(a)

Key Concepts

Sₙ1 Mechanism

Carbocation Stability

Nucleophiles

Watch next

Practice your electron-pushing skills by drawing a mechanism for the following S_N1 reactions.
(a)