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

Substitution Comparison

Organic Chemistry

7. Substitution Reactions

Substitution Comparison

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4:22 minutes

Problem 70e,f

Textbook Question

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

Verified step by step guidance

Step 1: Identify the starting material, 1-iodobutane, which is a primary alkyl halide. Primary alkyl halides typically undergo SN2 reactions with nucleophiles.

Step 2: For the first compound (butyl sulfide), recognize that the sulfur atom in the product suggests the nucleophile must contain a sulfur atom. A suitable nucleophile would be the thiolate ion (S²⁻ or RS⁻, where R is an alkyl group). The reaction mechanism involves the nucleophile attacking the carbon bonded to iodine, displacing the iodide ion.

Step 3: For the second compound (butyl acetate), observe the ester functional group. This indicates that the nucleophile must be an alkoxide ion (CH₃COO⁻, acetate ion). The acetate ion would attack the carbon bonded to iodine, displacing the iodide ion in an SN2 reaction.

Step 4: Write the general reaction mechanism for both cases. In an SN2 reaction, the nucleophile attacks the electrophilic carbon from the opposite side of the leaving group (iodine), leading to inversion of configuration at the carbon center.

Step 5: Ensure proper reaction conditions for each nucleophile. For thiolate ions, a polar aprotic solvent like DMSO or acetone is ideal to facilitate the SN2 reaction. For acetate ions, similar polar aprotic solvents can be used to enhance nucleophilicity and reaction efficiency.

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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 organic chemistry, common nucleophiles include hydroxide ions, alkoxides, and amines, which can attack electrophilic centers in substrates like alkyl halides.

Substitution Reactions

Substitution reactions involve the replacement of one functional group in a molecule with another. In the context of 1-iodobutane, these reactions can occur via two main mechanisms: SN1 and SN2. The choice of mechanism depends on factors such as the structure of the substrate and the nature of the nucleophile, influencing the reaction pathway and product formation.

1-Iodobutane Reactivity

1-Iodobutane is a primary alkyl halide, which makes it a good substrate for nucleophilic substitution reactions. Its reactivity is influenced by the leaving group ability of iodine and the steric accessibility of the carbon atom bonded to the iodine. Understanding the structure and reactivity of 1-iodobutane is crucial for predicting which nucleophiles will effectively react with it to form new compounds.

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Related Practice

Textbook Question

Draw the substitution products for each of the following S_N2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed:

c. (3R,4R)-3-bromo-4-methylhexane + CH₃O^-

d. (3R,4S)-3-bromo-4-methylhexane + CH₃O^-

Textbook Question

Propose a mechanism for the following reaction.

Textbook Question

Draw the substitution and elimination products.

Textbook Question

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

Textbook Question

Aldolase shows no activity if it is incubated with iodoacetic acid before fructose-1,6-bisphosphate is added to the reaction mixture. What causes this loss of activity?

Textbook Question

Predict the major products of the following substitutions.

Textbook Question

Predict the major products of the following substitutions.

Textbook Question

Chlorocyclohexane reacts with sodium cyanide (NaCN) in ethanol to give cyanocyclohexane. The rate of formation of cyanocyclohexane increases when a small amount of sodium iodide is added to the solution. Explain this acceleration in the rate.

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

Key Concepts

Nucleophiles

Substitution Reactions

1-Iodobutane Reactivity

Watch next

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