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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3:20 minutes

Problem 70h

Textbook Question

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?
h.

Verified step by step guidance

Step 1: Analyze the given compound structure. The compound shown contains a nitrile group (-C≡N) attached to a butane chain. This indicates that the nucleophile used in the reaction must have introduced the nitrile group.

Step 2: Recall the mechanism of nucleophilic substitution reactions. 1-Iodobutane is a primary alkyl halide, which typically undergoes SN2 reactions. In an SN2 reaction, the nucleophile attacks the carbon bonded to the leaving group (iodine) in a single step, displacing the leaving group.

Step 3: Identify the nucleophile that can introduce the nitrile group. The nucleophile in this case would be the cyanide ion (CN⁻), as it contains the nitrile group and is a strong nucleophile capable of participating in an SN2 reaction.

Step 4: Write the reaction mechanism. The cyanide ion (CN⁻) attacks the carbon atom bonded to iodine in 1-iodobutane, forming a new bond between the carbon and the cyanide group while displacing iodine as the leaving group.

Step 5: Summarize the reaction. The nucleophile required to form the given compound from 1-iodobutane is the cyanide ion (CN⁻). The reaction proceeds via an SN2 mechanism, resulting in the substitution of the iodine atom with the nitrile group.

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Key Concepts

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

Nucleophiles

Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. They are typically negatively charged or neutral molecules with lone pairs of electrons. In the context of organic reactions, nucleophiles attack electrophiles, which are electron-deficient species. Common examples include hydroxide ions (OH⁻), alkoxides (RO⁻), and amines (RNH₂).

SN2 Reaction Mechanism

The SN2 (substitution nucleophilic bimolecular) reaction is a type of nucleophilic substitution where the nucleophile attacks the electrophile simultaneously as the leaving group departs. This mechanism involves a single concerted step, leading to the inversion of configuration at the carbon center. It is favored by primary and some secondary alkyl halides, such as 1-iodobutane, due to steric accessibility.

Leaving Groups

Leaving groups are atoms or groups that can depart from the parent molecule during a chemical reaction, allowing for the formation of new bonds. A good leaving group is typically stable after departure, which is often the case for halides like iodide (I⁻). In SN2 reactions, the quality of the leaving group significantly influences the reaction rate, with better leaving groups facilitating faster reactions.

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Related Practice

Textbook Question

2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is stereospecific—that is, the stereoisomers obtained as products depend on the stereoisomer used as a reactant. Recall that because 2-acetoxycyclohexyl tosylate has two asymmetric centers, it has four stereoisomers—two are cis and two are trans. Explain the following observations:

c. A trans reactant is more reactive than a cis reactant.

Textbook Question

Which substitution reaction takes place more rapidly?

Textbook Question

Which substitution reaction takes place more rapidly?

Textbook Question

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?

Textbook Question

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

a. 2-methoxybutane

Textbook Question

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

b. 1-methoxybutane

Textbook Question

b. Both trans reactants form the same racemic mixture.

Textbook Question

The rate of the reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of the reaction of methyl iodide with triethylamine was measured in the same solvent. The concentration of the reagents was the same in both experiments.

b. The same experiment was done using isopropyl iodide instead of methyl iodide. Which reaction had the larger rate constant?

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What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane? h.

Key Concepts

Nucleophiles

SN2 Reaction Mechanism

Leaving Groups

Watch next

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?
h.