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

Previous problemNext problem

15:16 minutes

Problem 40c,d

Textbook Question

Give the substitution products expected from solvolysis of each compound by heating in ethanol.
(c)
(d)

Verified step by step guidance

Step 1: Identify the type of halide in each compound. Both compounds contain a bromine atom attached to a carbon atom. In compound (c), bromine is attached to a secondary carbon, while in compound (d), bromine is attached to a tertiary carbon.

Step 2: Recognize the reaction conditions. Solvolysis in ethanol typically proceeds via an SN1 mechanism, especially for secondary and tertiary alkyl halides. This involves the formation of a carbocation intermediate after the departure of the bromide ion.

Step 3: Analyze the stability of the carbocation intermediates. In compound (c), the secondary carbocation formed is moderately stable. In compound (d), the tertiary carbocation formed is highly stable due to hyperconjugation and inductive effects from the surrounding alkyl groups.

Step 4: Predict the substitution product. Ethanol acts as the nucleophile in this reaction. After the carbocation is formed, ethanol will attack the positively charged carbon, leading to the formation of an ethyl ether product (R-OCH2CH3).

Step 5: Consider any potential rearrangements. For compound (c), no rearrangement is expected as the secondary carbocation is relatively stable. For compound (d), no rearrangement is needed as the tertiary carbocation is already highly stable.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

15m

Play a video:

Was this helpful?

Key Concepts

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

Solvolysis

Solvolysis is a type of nucleophilic substitution reaction where a solvent acts as a nucleophile. In organic chemistry, this often involves the reaction of an alkyl halide with a solvent like ethanol, leading to the formation of substitution products. The reaction typically proceeds through either an SN1 or SN2 mechanism, depending on the structure of the substrate and the conditions of the reaction.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution can occur via two primary mechanisms: SN1 and SN2. The SN1 mechanism involves a two-step process where the leaving group departs first, forming a carbocation intermediate, followed by nucleophilic attack. In contrast, the SN2 mechanism is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs, leading to an inversion of configuration at the carbon center.

Ethanol as a Solvent

Ethanol is a polar protic solvent that can stabilize ions and facilitate nucleophilic substitution reactions. Its ability to donate hydrogen bonds makes it effective in solvolysis, as it can stabilize the carbocation formed in SN1 reactions or assist in the nucleophilic attack in SN2 reactions. The choice of solvent can significantly influence the reaction pathway and the products formed.

Watch next

Master Drawing the SN1 Mechanism with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

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

c. n-propyl bromide or allyl bromide

d. 1-bromo-2,2-dimethylpropane or 2-bromopropane

Textbook Question

Predict the compound in each pair that will undergo solvolysis (in aqueous ethanol) more rapidly.

(c)

(d)

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

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

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)

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

Show more practices