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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3:48 minutes

Problem 15c,d

Textbook Question

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.
c. 1-iodobutane
d. CH₃—(CH₂)₃—CN

Verified step by step guidance

Step 1: Understand the SN2 reaction mechanism. SN2 reactions involve a single-step nucleophilic substitution where the nucleophile attacks the electrophilic carbon and simultaneously displaces the leaving group. This reaction is favored in primary alkyl halides like 1-chlorobutane.

Step 2: For part c (conversion to 1-iodobutane), select an appropriate nucleophile. Use iodide ion (I⁻) as the nucleophile because it is a strong nucleophile and can replace the chlorine atom in 1-chlorobutane. The reaction can be carried out in a polar aprotic solvent like acetone to favor the SN2 mechanism.

Step 3: Write the reaction for part c. The iodide ion attacks the carbon bonded to chlorine in 1-chlorobutane, displacing the chloride ion (Cl⁻) and forming 1-iodobutane. The reaction can be represented as: CH₃(CH₂)₃Cl + I⁻ → CH₃(CH₂)₃I + Cl⁻.

Step 4: For part d (conversion to CH₃—(CH₂)₃—CN), select an appropriate nucleophile. Use cyanide ion (CN⁻) as the nucleophile because it is a strong nucleophile and can replace the chlorine atom in 1-chlorobutane. Again, use a polar aprotic solvent like acetone to favor the SN2 mechanism.

Step 5: Write the reaction for part d. The cyanide ion attacks the carbon bonded to chlorine in 1-chlorobutane, displacing the chloride ion (Cl⁻) and forming CH₃—(CH₂)₃—CN. The reaction can be represented as: CH₃(CH₂)₃Cl + CN⁻ → CH₃(CH₂)₃CN + Cl⁻.

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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, where the nucleophile approaches the electrophile from the opposite side of the leaving group, leading to inversion of configuration. Understanding this mechanism is crucial for predicting the outcomes of reactions involving alkyl halides like 1-chlorobutane.

Nucleophiles and Electrophiles

In organic chemistry, nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept electron pairs. In the context of SN2 reactions, the nucleophile attacks the electrophilic carbon atom of the alkyl halide, displacing the leaving group. Identifying strong nucleophiles, such as iodide ions (I-) or cyanide ions (CN-), is essential for successfully converting 1-chlorobutane into the desired products.

Leaving Groups

A leaving group is an atom or group that can depart from the parent molecule during a chemical reaction, facilitating the formation of new bonds. In SN2 reactions, the quality of the leaving group significantly affects the reaction rate; better leaving groups, such as iodide (I-) compared to chloride (Cl-), enhance the reaction's efficiency. Understanding the role of leaving groups is vital for predicting the feasibility of converting 1-chlorobutane into 1-iodobutane and butanenitrile.

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Related Practice

Textbook Question

Starting with an alkyl halide, how could the following compounds be prepared?

c. butylmethylamine

Textbook Question

The reaction of an amine with an alkyl halide gives an ammonium salt.R3N amine + R'—X alkyl halide —> R3(N+)—R' X- ammonium salt The rate of this SN2 reaction is sensitive to the polarity of the solvent. 1. Draw an energy diagram for this reaction in a nonpolar solvent and another in a polar solvent. 2. Consider the nature of the transition state, and explain why this reaction should be sensitive to the polarity of the solvent. 3. Predict whether it will be faster or slower in a more polar solvent.

Textbook Question

Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second.

c. Show another S_N2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces 1-methoxybutane.

Textbook Question

Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds.

e. CH₃—(CH₂)₃—C≡CH

f. CH₃CH₂—O—(CH₂)₃—CH₃

g. CH₃—(CH₂)₃—NH₂

Textbook Question

Show how each compound might be synthesized by the SN2 displacement of an alkyl halide.

e. H₂C=CH—CH₂CN

f. H—C≡C—CH₂CH₂CH₃

Textbook Question

Give two syntheses for (CH₃)₂CH—O—CH₂CH₃, and explain which synthesis is better.

Textbook Question

For each pair, choose the nucleophile that would react most quickly in an S_N2 reaction (assume H₂O is the solvent).

(a) F^- vs Br^-

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Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds.c. 1-iodobutaned. CH3—(CH2)3—CN

Key Concepts

SN2 Reaction Mechanism

Nucleophiles and Electrophiles

Leaving Groups

Watch next

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.
c. 1-iodobutane
d. CH₃—(CH₂)₃—CN