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

Nucleophilic Substitution

Organic Chemistry

7. Substitution Reactions

Nucleophilic Substitution

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3:23 minutes

Problem 15c,d

Textbook Question

What is the product of the reaction of bromoethane with each of the following nucleophiles?
c. (CH₃)₃N
d. CH₃CH₂S^-

Verified step by step guidance

Step 1: Identify the type of reaction. Bromoethane (C2H5Br) is a primary alkyl halide, and the reaction with nucleophiles typically proceeds via an SN2 mechanism due to the unhindered nature of the carbon attached to the bromine atom.

Step 2: Analyze the nucleophile in part (c). The nucleophile is trimethylamine ((CH3)3N), which is a neutral nucleophile with a lone pair of electrons on the nitrogen atom. In this case, the reaction will likely result in the formation of a quaternary ammonium salt through nucleophilic substitution.

Step 3: Write the reaction for part (c). The nitrogen in (CH3)3N attacks the carbon bonded to the bromine in bromoethane, displacing the bromide ion (Br⁻) and forming a quaternary ammonium salt: [(CH3)3N⁺CH2CH3]Br⁻.

Step 4: Analyze the nucleophile in part (d). The nucleophile is ethanethiolate (CH3CH2S⁻), which is a strong nucleophile due to the negatively charged sulfur atom. This nucleophile will also undergo an SN2 reaction with bromoethane.

Step 5: Write the reaction for part (d). The sulfur atom in CH3CH2S⁻ attacks the carbon bonded to the bromine in bromoethane, displacing the bromide ion (Br⁻) and forming the product CH3CH2SCH2CH3 (ethyl ethyl sulfide).

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Key Concepts

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

Nucleophilicity

Nucleophilicity refers to the ability of a species to donate an electron pair to an electrophile, forming a chemical bond. Strong nucleophiles, such as thiolates or amines, are more likely to react with electrophiles like bromoethane. The strength of a nucleophile is influenced by factors such as charge, electronegativity, and steric hindrance.

Substitution Reactions

Substitution reactions involve the replacement of one functional group in a molecule with another. In the case of bromoethane, nucleophiles can perform either an SN1 or SN2 mechanism, depending on their structure and the conditions. Understanding these mechanisms is crucial for predicting the products of the reaction.

Steric Hindrance

Steric hindrance refers to the prevention of reactions due to the spatial arrangement of atoms within a molecule. In nucleophilic substitution, bulky nucleophiles like (CH3)3N may experience steric hindrance, affecting their ability to approach and react with the electrophile. This concept is essential for determining the reaction pathway and product formation.

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Textbook Question

Predict the product of the following substitution/addition reactions involving phenoxides. [Because this problem represents a review of current and previous material, section numbers have been provided for your reference.]

(d)

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The following functional-group interchange is a useful synthesis of aldehydes.

Textbook Question

What is the product of the reaction of bromoethane with each of the following nucleophiles?

a. CH₃CH₂CH₂O⁻

b. CH₃C≡C⁻

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a. Identify the intermediate (A) and show the mechanism for its formation.

Textbook Question

Strawberry growers have used large quantities of methyl bromide (b.p. 4 °C) to sterilize the soil before planting their crops. Like some of the freons, methyl bromide can diffuse up into the stratosphere, where it damages the protective ozone layer. Agricultural chemists have suggested using methyl iodide (b.p. 43 °C) as a replacement for methyl bromide. Why is methyl iodide likely to be more toxic to agricultural pests (and people) than methyl bromide? Why is methyl iodide less likely to reach the stratosphere than methyl bromide?

Textbook Question

Which substitution reaction takes place more rapidly?

a. CH₃CH₂Br + H₂O or CH₃CH₂Br + HO⁻

Textbook Question

Draw all the products of the following reaction:

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