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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6:18 minutes

Problem 18a,b

Textbook Question

Draw the stereoisomers that are formed from the following S_N1 reactions:
a. 3-bromo-3-methylpentane and methanol
b. 3-chloro-3-methylhexane and methanol

Verified step by step guidance

Step 1: Understand the SN1 reaction mechanism. SN1 reactions proceed via a two-step mechanism: (1) the leaving group departs, forming a carbocation intermediate, and (2) the nucleophile attacks the carbocation. The carbocation intermediate is planar, allowing for the formation of stereoisomers.

Step 2: Analyze the substrate in part (a), 3-bromo-3-methylpentane. When the bromine atom leaves, a tertiary carbocation is formed at the 3rd carbon. Tertiary carbocations are stable due to hyperconjugation and inductive effects.

Step 3: Consider the nucleophile, methanol (CH₃OH). Methanol can attack the planar carbocation from either side, leading to the formation of two stereoisomers: one with the nucleophile on the front side and one on the back side. These stereoisomers are enantiomers.

Step 4: Repeat the analysis for part (b), 3-chloro-3-methylhexane. When the chlorine atom leaves, a tertiary carbocation is formed at the 3rd carbon. Similar to part (a), the planar carbocation allows methanol to attack from either side, forming two stereoisomers.

Step 5: Draw the stereoisomers for both reactions. For each reaction, depict the two enantiomers formed by the attack of methanol on the planar carbocation. Ensure that the stereochemistry is clearly indicated in the drawings, showing the nucleophile on opposite sides of the plane.

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Key Concepts

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

Stereoisomerism

Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This can lead to different physical and chemical properties. In organic chemistry, stereoisomers include enantiomers and diastereomers, which are crucial for understanding the outcomes of reactions like SN1.

SN1 Reaction Mechanism

The SN1 (nucleophilic substitution unimolecular) reaction mechanism involves two main steps: the formation of a carbocation intermediate and the subsequent nucleophilic attack. The rate-determining step is the formation of the carbocation, which is influenced by the stability of the carbocation and the solvent used. This mechanism often leads to racemization due to the planar nature of the carbocation.

Carbocation Stability

Carbocation stability is a key factor in determining the outcome of SN1 reactions. Carbocations are positively charged species that can be classified based on their degree of substitution: tertiary (most stable), secondary, and primary (least stable). The stability of the carbocation affects the rate of the reaction and the types of stereoisomers formed, as more stable carbocations are more likely to form and react.

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Related Practice

Textbook Question

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

(a) (CH₃CH₂)₂CH—Cl or (CH₃)₃C—Cl

(b)

Textbook Question

Choose the member of each pair that will react faster by the S_N1 mechanism.

a. 1-bromopropane or 2-bromopropane

b. 2-bromo-2-methylbutane or 2-bromo-3-methylbutane

Textbook Question

Furfuryl chloride can undergo substitution by both S_N2 and S_N1 mechanisms. Because it is a 1° alkyl halide, we expect S_N2 but not S_N1 reactions. Draw a mechanism for the S_N1 reaction shown below, paying careful attention to the structure of the intermediate. How can this primary halide undergo S_N1 reactions?

Textbook Question

Optically active butan-2-ol racemizes in dilute acid. Propose a mechanism for this racemization.

Textbook Question

Rank the following from most reactive to least reactive in an S_N1 reaction:

Textbook Question

Which reacts faster in an S_N1 reaction?

Textbook Question

The bromoalkanes shown below participate in S_N1 reactions with the relative rates shown. Explain this trend. relative rate:

Textbook Question

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

(b)

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Draw the stereoisomers that are formed from the following SN1 reactions: a. 3-bromo-3-methylpentane and methanol b. 3-chloro-3-methylhexane and methanol

Key Concepts

Stereoisomerism

SN1 Reaction Mechanism

Carbocation Stability

Watch next

Draw the stereoisomers that are formed from the following S_N1 reactions:
a. 3-bromo-3-methylpentane and methanol
b. 3-chloro-3-methylhexane and methanol