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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1:13 minutes

Problem 6-15a

Textbook Question

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.
a. butan-1-ol

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: Identify the nucleophile and solvent required for the reaction. To convert 1-chlorobutane into butan-1-ol, the nucleophile should be hydroxide ion (OH⁻), which can be provided by a strong base like NaOH or KOH. The solvent should be polar aprotic, such as acetone or DMSO, to favor the SN2 mechanism.

Step 3: Write the chemical equation for the reaction. The hydroxide ion will attack the carbon bonded to the chlorine atom in 1-chlorobutane, displacing the chlorine atom as Cl⁻ and forming butan-1-ol. The reaction can be represented as:

{CH}_{3} {CH}_{2} {CH}_{2} {CH}_{2} (Cl) + OH \to {CH}_{3} {CH}_{2} {CH}_{2} {CH}_{2} (OH) + Cl ⁻

Step 4: Consider reaction conditions. Ensure the reaction is carried out under conditions that favor SN2, such as using a polar aprotic solvent and maintaining a low temperature to avoid competing elimination reactions.

Step 5: Verify the product. After the reaction, confirm the formation of butan-1-ol by analyzing the product using techniques like IR spectroscopy (look for the O-H stretch around 3200-3600 cm⁻¹) or NMR spectroscopy (look for the characteristic signals of the hydroxyl group and the alkyl chain).

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Key Concepts

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

SN2 Reactions

SN2 (Substitution Nucleophilic Bimolecular) reactions involve a nucleophile attacking an electrophilic carbon atom, resulting in the simultaneous displacement of a leaving group. This mechanism is characterized by a single concerted step, where the nucleophile approaches the carbon from the opposite side of the leaving group, leading to inversion of configuration. Understanding this mechanism is crucial for predicting the outcome of reactions involving primary alkyl halides like 1-chlorobutane.

Nucleophiles

Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. In the context of SN2 reactions, a strong nucleophile is essential for effectively displacing the leaving group. Common nucleophiles include hydroxide ions (OH-) and alkoxide ions (RO-), which can be used to convert 1-chlorobutane into butan-1-ol by attacking the carbon atom bonded to the chlorine.

Leaving Groups

A leaving group is an atom or group that can depart with a pair of electrons in a substitution or elimination reaction. The effectiveness of a leaving group significantly influences the rate and feasibility of SN2 reactions. In the case of 1-chlorobutane, the chloride ion (Cl-) is a good leaving group, allowing for the successful conversion to butan-1-ol when a suitable nucleophile is introduced.

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Textbook Question

For each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second order (SN2).

c. 1-iodo-1-methylcyclohexane + ethanol

Textbook Question

The following reaction takes place under second-order conditions (strong nucleophile), yet the structure of the product shows rearrangement. Also, the rate of this reaction is several thousand times faster than the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism to explain the enhanced rate and rearrangement observed in this unusual reaction. (“Et” is the abbreviation for ethyl.)

Textbook Question

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

Textbook Question

For each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (S_N1) or second order (S_N2).

a. 2-chloro-2-methylbutane + CH₃COOH

b. isobutylbromide + sodium methoxide

Textbook Question

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

b. 1-fluorobutane

Textbook Question

A solution of pure (S)-2-iodobutane ([α] = +15.90°) in acetone is allowed to react with radioactive iodide, ¹³¹I^–, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°.

b. What does this result suggest about the mechanism of the reaction of 2-iodobutane with iodide ion?

Textbook Question

Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below. In each case, explain what unwanted reactions might produce undesirable impurities in the product.

Textbook Question

Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.

(c)

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