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

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

Organic Chemistry

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

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4:33 minutes

Problem 63b

Textbook Question

What products (including stereoisomers, if applicable) are formed from the reaction of 3-bromo-3-methylpentane:
b. with H₂O?

Verified step by step guidance

Identify the type of reaction: The reaction involves 3-bromo-3-methylpentane and water (H₂O). Since the substrate is a tertiary alkyl halide, this reaction is likely to proceed via an SN1 mechanism, which involves a two-step process: carbocation formation and nucleophilic attack.

Step 1: Carbocation formation. The bromine atom (Br) in 3-bromo-3-methylpentane is a good leaving group. It will leave, forming a tertiary carbocation at the 3rd carbon. This step is the rate-determining step of the SN1 mechanism.

Step 2: Nucleophilic attack. The water molecule (H₂O) acts as a nucleophile and attacks the positively charged carbocation, forming an oxonium ion intermediate (R-OH₂⁺).

Step 3: Deprotonation. The oxonium ion intermediate loses a proton (H⁺) to form the final alcohol product. This step is facilitated by the surrounding water molecules acting as a base.

Consider stereochemistry: Since the carbocation intermediate is planar, the nucleophile (H₂O) can attack from either side, leading to the formation of a racemic mixture of stereoisomers (if applicable). Analyze the structure of the product to determine if stereoisomers are formed.

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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 the case of 3-bromo-3-methylpentane reacting with water, the bromine atom acts as the leaving group, while water, acting as a nucleophile, attacks the carbon atom bonded to the bromine. This process can lead to the formation of alcohols.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. When 3-bromo-3-methylpentane undergoes nucleophilic substitution, the reaction can produce different stereoisomers depending on the configuration of the chiral center. Understanding stereochemistry is crucial for predicting the types of products formed, including any enantiomers or diastereomers.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step process by which reactants transform into products. For the reaction of 3-bromo-3-methylpentane with water, the mechanism can be either SN1 or SN2, depending on the conditions. The SN1 mechanism involves a two-step process with a carbocation intermediate, while SN2 is a one-step process where the nucleophile attacks the substrate directly, influencing the stereochemical outcome of the reaction.

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Textbook Question

What are the products of the following reactions?

Textbook Question

Explain how each of the following changes affect the rate of the reaction of 1-bromobutane with ethoxide ion in DMF.

c. The alkyl halide is changed to 1-chlorobutane.

d. The alkyl halide is changed to 2-bromobutane.

Textbook Question

What are the products of the following reactions?

Textbook Question

Draw the products of each of the following S_N2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

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

Textbook Question

Which of these reactions are likely to produce both elimination and substitution products?

a. 2-bromopentane + NaOCH₃

b. 3-bromo-3-methylpentane + NaOMe. (Me = methyl, CH₃)

c. 2-bromo-3-ethylpentane + NaOH

Textbook Question

For each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products.

c. chlorocyclohexane+NaOCH₃in CH₃OH

d. chlorocyclohexane + NaOC(CH₃)₃ in (CH₃)₃COH

Textbook Question

Silver-assisted solvolysis of bromomethylcyclopentane in methanol gives a complex product mixture of the following five compounds. Propose mechanisms to account for these products.

(a)

Textbook Question

Deuterium (D) is the isotope of hydrogen of mass number 2, with a proton and a neutron in its nucleus. The chemistry of deuterium is nearly identical to the chemistry of hydrogen, except that the C―D bond is slightly (5.0 kJ/mol, or 1.2 kcal/mol) stronger than the C―H bond. Reaction rates tend to be slower if a C―D bond (as opposed to a C―H bond) is broken in a rate-limiting step. This effect on the rate is called a kinetic isotope effect. (Review PROBLEM 4-57)

a. Propose a mechanism to explain each product in the following reaction.

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What products (including stereoisomers, if applicable) are formed from the reaction of 3-bromo-3-methylpentane:b. with H2O?

Key Concepts

Nucleophilic Substitution

Stereochemistry

Reaction Mechanisms

Watch next

What products (including stereoisomers, if applicable) are formed from the reaction of 3-bromo-3-methylpentane:
b. with H₂O?