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

SN2 Reaction

Organic Chemistry

7. Substitution Reactions

SN2 Reaction

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7:03 minutes

Problem 6c,d

Textbook Question

Draw the products obtained from the S_N2 reaction of:
c. (S)-3-chlorohexane and hydroxide ion.
d. 3-iodopentane and hydroxide ion.

Verified step by step guidance

Step 1: Understand the SN2 reaction mechanism. The SN2 reaction is a bimolecular nucleophilic substitution reaction where the nucleophile attacks the electrophilic carbon from the opposite side of the leaving group, leading to an inversion of configuration at the carbon center.

Step 2: For part (c), identify the substrate and nucleophile. The substrate is (S)-3-chlorohexane, which has a chiral center at carbon-3. The nucleophile is the hydroxide ion (OH⁻), and the leaving group is the chloride ion (Cl⁻).

Step 3: Predict the stereochemical outcome for part (c). Since the SN2 reaction proceeds with inversion of configuration, the product will have the opposite configuration at the chiral center. The product will be (R)-3-hexanol, where the hydroxide ion replaces the chloride ion.

Step 4: For part (d), identify the substrate and nucleophile. The substrate is 3-iodopentane, which does not have a chiral center. The nucleophile is the hydroxide ion (OH⁻), and the leaving group is the iodide ion (I⁻).

Step 5: Predict the product for part (d). Since there is no chiral center, the SN2 reaction will simply result in the substitution of the iodide ion with the hydroxide ion, forming 3-pentanol as the product.

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Key Concepts

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

SN2 Reaction Mechanism

The SN2 (substitution nucleophilic bimolecular) reaction is a type of nucleophilic substitution where a nucleophile attacks an electrophile, resulting in the simultaneous displacement of a leaving group. This mechanism involves a single concerted step, leading to the formation of a transition state where both the nucleophile and the leaving group are partially bonded to the carbon atom. The reaction typically occurs with primary or secondary substrates due to steric hindrance.

Stereochemistry in SN2 Reactions

Stereochemistry plays a crucial role in SN2 reactions, as the nucleophile attacks the electrophile from the opposite side of the leaving group, leading to an inversion of configuration at the chiral center. This means that if the starting material is chiral, the product will have the opposite configuration. Understanding this inversion is essential for predicting the stereochemical outcome of reactions involving chiral substrates.

Nucleophilicity and Leaving Groups

Nucleophilicity refers to the ability of a species to donate an electron pair to form a new bond, while leaving groups are atoms or groups that can depart with a pair of electrons during a reaction. In SN2 reactions, strong nucleophiles, such as hydroxide ions, effectively attack the electrophile, while good leaving groups, like chloride or iodide ions, facilitate the reaction by stabilizing the transition state. The strength of both factors significantly influences the reaction rate and product formation.

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