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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7:01 minutes

Problem 26d

Textbook Question

Propose a mechanism involving a hydride shift or an alkyl shift for each solvolysis reaction. Explain how each rearrangement forms a more stable intermediate.
Hint: Most rearrangements convert 2° (or incipient 1°) carbocations to 3° or resonance-stabilized carbocations.
(d)

Verified step by step guidance

The reaction begins with the ionization of the alkyl iodide (CH2I group) to form a primary carbocation. This occurs because the iodide ion (I⁻) is a good leaving group, and the reaction is facilitated by the polar protic solvent (ethanol, CH3CH2OH).

The initially formed primary carbocation is unstable. To increase stability, a hydride shift occurs. A hydrogen atom (along with its bonding electrons) from the adjacent carbon migrates to the carbocation, converting it into a more stable secondary carbocation.

The secondary carbocation undergoes further rearrangement via an alkyl shift. A methyl group (CH3) from a neighboring carbon migrates to the carbocation, forming a tertiary carbocation, which is even more stable due to hyperconjugation and inductive effects.

Once the tertiary carbocation is formed, the ethanol solvent acts as a nucleophile and attacks the carbocation. This results in the formation of an ether product (CH3CH2O group attached to the carbon).

The reaction produces two products: one where the rearranged tertiary carbocation reacts with ethanol to form the major product, and another where the primary carbocation reacts directly with ethanol to form the minor product. The major product is favored due to the stability of the tertiary carbocation intermediate.

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Key Concepts

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

Carbocation Stability

Carbocations are positively charged carbon species that can rearrange to form more stable intermediates. Stability increases from primary (1°) to secondary (2°) to tertiary (3°) carbocations due to hyperconjugation and inductive effects. In solvolysis reactions, the formation of a more stable carbocation intermediate often drives the reaction forward, allowing for subsequent nucleophilic attack.

Hydride and Alkyl Shifts

Hydride shifts involve the migration of a hydrogen atom with its bonding electrons from one carbon to an adjacent positively charged carbon, while alkyl shifts involve the movement of an alkyl group. These shifts occur to stabilize carbocations by converting less stable carbocations into more stable ones, such as transforming a secondary carbocation into a tertiary carbocation, which is more favorable energetically.

Solvolysis Mechanism

Solvolysis is a nucleophilic substitution reaction where a solvent acts as a nucleophile, typically resulting in the formation of alcohols or ethers. In the provided reaction, the alkyl iodide undergoes solvolysis in ethanol, leading to the formation of two products. The mechanism often involves the formation of a carbocation intermediate, which can rearrange to enhance stability before the nucleophile attacks.

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Related Practice

Textbook Question

Allylic halides have the structure

a. Show how the first-order ionization of an allylic halide leads to a resonance-stabilized cation.

Textbook Question

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

(d) a 3° alkyl bromide

Textbook Question

Give the substitution products expected from solvolysis of each compound by heating in ethanol.

(c)

(d)

Textbook Question

Propose a mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether.

Textbook Question

Predict the products of the following S_N2 reactions.

(c)

(d)

Textbook Question

Choose the member of each pair that will react faster by the SN1 mechanism.

e. 2-iodo-2-methylbutane or tert-butyl chloride

f. 2-bromo-2-methylbutane or ethyl iodide

Textbook Question

When tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether.

b. What happens to the rate if the concentration of tert-butyl bromide is tripled and the concentration of ethanol is doubled?

c. What happens to the rate if the temperature is raised?

Textbook Question

tert-Butyl chloride undergoes solvolysis in both acetic acid and formic acid. Solvolysis occurs 5000 times faster in one of these two solvents than in the other. In which solvent is solvolysis faster? Explain your answer. (Hint: Formic acid is more polar than acetic acid.)

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Propose a mechanism involving a hydride shift or an alkyl shift for each solvolysis reaction. Explain how each rearrangement forms a more stable intermediate.Hint: Most rearrangements convert 2° (or incipient 1°) carbocations to 3° or resonance-stabilized carbocations.(d)

Key Concepts

Carbocation Stability

Hydride and Alkyl Shifts

Solvolysis Mechanism

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Propose a mechanism involving a hydride shift or an alkyl shift for each solvolysis reaction. Explain how each rearrangement forms a more stable intermediate.
Hint: Most rearrangements convert 2° (or incipient 1°) carbocations to 3° or resonance-stabilized carbocations.
(d)