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

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

Organic Chemistry

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

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Problem 59a

Textbook Question

For each pair, choose the haloalkane that would react most quickly in an S_N1 or E1 reaction.
(a)

Verified step by step guidance

Step 1: Understand the reaction mechanism. SN1 and E1 reactions proceed via a carbocation intermediate. The rate of these reactions depends on the stability of the carbocation formed after the leaving group departs.

Step 2: Analyze the structures of the haloalkanes. The first structure is a tertiary alkyl bromide, while the second structure is a tertiary alkyl bromide with an adjacent oxygen atom bonded to the carbon chain.

Step 3: Consider the effect of the oxygen atom in the second structure. Oxygen is electronegative and can stabilize the carbocation through resonance or inductive effects, making the carbocation more stable.

Step 4: Compare the carbocation stability. The carbocation formed from the second structure (with the oxygen atom) is more stable due to the additional stabilization provided by the oxygen atom, compared to the carbocation formed from the first structure.

Step 5: Conclude which haloalkane reacts faster. Since the second structure forms a more stable carbocation, it will react more quickly in an SN1 or E1 reaction.

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Key Concepts

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

Sn1 and E1 Reactions

Sn1 and E1 reactions are unimolecular nucleophilic substitution and elimination reactions, respectively. They involve the formation of a carbocation intermediate after the leaving group departs. The rate of these reactions depends solely on the concentration of the substrate, making them first-order reactions. The stability of the carbocation significantly influences the reaction rate, with more stable carbocations leading to faster reactions.

Carbocation Stability

Carbocation stability is a crucial factor in determining the rate of Sn1 and E1 reactions. Carbocations are stabilized by hyperconjugation and inductive effects from adjacent alkyl groups. Tertiary carbocations are more stable than secondary, which are more stable than primary. The more stable the carbocation, the faster the reaction will proceed, as it is less likely to revert to the starting material.

Leaving Group Ability

The ability of a leaving group to depart from a molecule is vital in Sn1 and E1 reactions. Good leaving groups, such as bromide (Br-), can stabilize the negative charge after leaving, facilitating the formation of the carbocation. In contrast, poor leaving groups hinder the reaction rate. The choice of leaving group can significantly affect the overall reactivity of haloalkanes in these types of reactions.

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For each pair, choose the haloalkane that would react most quickly in an SN1 or E1 reaction.(a)

Key Concepts

S<sub>n</sub>1 and E1 Reactions

Carbocation Stability

Leaving Group Ability

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For each pair, choose the haloalkane that would react most quickly in an S_N1 or E1 reaction.
(a)