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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4:10 minutes

Problem 70g

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the given compound. The structure shows a butyl group attached to an oxygen atom, which is further connected to a carbonyl group (C=O) and a methyl group. This indicates the compound is an ester, specifically butyl acetate.

Step 2: Identify the starting material. The problem states that 1-iodobutane is the starting material. This compound is a primary alkyl halide, which is reactive in nucleophilic substitution reactions.

Step 3: Determine the nucleophile required to form the ester. To form butyl acetate, the nucleophile must provide the acetate group (CH3COO−). This suggests that the nucleophile is acetate ion (CH3COO−).

Step 4: Consider the reaction mechanism. The reaction likely proceeds via an SN2 mechanism because 1-iodobutane is a primary alkyl halide, which favors bimolecular nucleophilic substitution. The acetate ion attacks the carbon attached to the iodine atom, displacing the iodide ion.

Step 5: Summarize the reaction. The nucleophile (CH3COO−) reacts with 1-iodobutane in an SN2 reaction to form butyl acetate as the product, with iodide ion (I−) as the leaving 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 nucleophilic substitution reactions, such as SN2, nucleophiles attack electrophilic centers, like the carbon atom bonded to a leaving group, facilitating the substitution process.

SN2 Reaction Mechanism

The SN2 (substitution nucleophilic bimolecular) reaction is a type of nucleophilic substitution where the nucleophile attacks the electrophile from the opposite side of the leaving group, resulting in a concerted mechanism. This reaction is characterized by a single transition state and leads to inversion of configuration at the carbon center. It is favored by primary substrates, like 1-iodobutane, due to less steric hindrance.

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, such as iodide in the case of 1-iodobutane. The ability of a leaving group to stabilize its negative charge is crucial in determining the rate and feasibility of nucleophilic substitution reactions.

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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:

a. Both cis reactants form an optically active trans product, but each cis reactant forms a different trans product.