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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3:43 minutes

Problem 14e

Textbook Question

Predict the major products of the following substitutions.
e. 1-chloropentane + NaI →

Verified step by step guidance

Step 1: Recognize the type of substitution reaction. This reaction involves 1-chloropentane (a primary alkyl halide) and sodium iodide (NaI). Sodium iodide is a good nucleophile, and the reaction is likely to proceed via an SN2 mechanism due to the primary nature of the alkyl halide.

Step 2: Understand the SN2 mechanism. In an SN2 reaction, the nucleophile (I⁻) attacks the carbon atom bonded to the leaving group (Cl) from the opposite side, leading to a single-step reaction where the leaving group is displaced.

Step 3: Identify the leaving group. In this case, the leaving group is chloride (Cl⁻), which is a relatively good leaving group. It will be replaced by the iodide ion (I⁻).

Step 4: Write the chemical equation for the substitution reaction. The reaction can be represented as:

{CH 3}_{4} CH (Cl) + NaI \to {CH 3}_{4} CH (I) + NaCl

Step 5: Predict the major product. The major product will be 1-iodopentane, as the iodide ion replaces the chloride ion in the SN2 reaction. The reaction proceeds with inversion of configuration at the carbon center, but since the carbon is not chiral, this detail does not affect the product's structure.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, NaI provides iodide ions (I-) as the nucleophile, which can attack the carbon atom bonded to the chlorine in 1-chloropentane, leading to the formation of a new compound.

SN2 Mechanism

The SN2 mechanism is a type of nucleophilic substitution characterized by a single concerted step where the nucleophile attacks the electrophile from the opposite side of the leaving group. This results in the inversion of configuration at the carbon center. In the reaction of 1-chloropentane with NaI, the SN2 pathway is favored due to the primary nature of the substrate.

Leaving Group Ability

The ability of a leaving group to depart from a molecule is crucial in determining the outcome of substitution reactions. Chlorine, as a leaving group, is relatively good because it can stabilize the negative charge after leaving. The efficiency of the substitution reaction is influenced by the strength of the leaving group, with better leaving groups facilitating faster reactions.