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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2:52 minutes

Problem 99a,b

Textbook Question

What are the products of the following reactions?
a.
b.

Verified step by step guidance

Step 1: Analyze the first reaction. The reactant is an alkyl iodide (1-iodobutane), and the reagent is triethylamine ((CH₃CH₂)₃N). This reaction involves nucleophilic substitution, where the iodide group is replaced by the nucleophile.

Step 2: In the first reaction, triethylamine acts as a nucleophile. It will attack the carbon bonded to iodine, displacing the iodide ion (I⁻) and forming a new bond between the carbon and the nitrogen of triethylamine.

Step 3: Analyze the second reaction. The reactant is a chiral alkyl chloride (2-chlorobutane), and the reagent is a thiolate ion (CH₃S⁻). This reaction also involves nucleophilic substitution, where the chloride group is replaced by the nucleophile.

Step 4: In the second reaction, the thiolate ion (CH₃S⁻) will attack the carbon bonded to chlorine, displacing the chloride ion (Cl⁻) and forming a new bond between the carbon and the sulfur of the thiolate group.

Step 5: Consider stereochemistry for the second reaction. Since the carbon bonded to chlorine is chiral, the nucleophilic substitution may proceed via an SN2 mechanism, leading to inversion of configuration at the chiral center.

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity and the types of products that can be formed in a reaction. Common functional groups include alcohols, carboxylic acids, and amines.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is essential for understanding isomerism, where compounds with the same molecular formula can have different structures and properties. Stereochemical considerations can influence the products of reactions, especially in chiral environments.

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Related Practice

Textbook Question

For which of the following reactions would you expect elimination to be more favored than substitution?

(d)

Textbook Question

When the following compound undergoes solvolysis in ethanol, three products are obtained. Propose a mechanism to account for the formation of these products.

Textbook Question

Draw the substitution and elimination products for the following reactions, showing the configuration of each product:

c. 1-chloro-1-methylcyclohexane + CH₃O⁻

d. 1-chloro-1-methylcyclohexane + CH₃OH

Textbook Question

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

a. (R)-2-bromohexane + high concentration of CH₃O⁻

b. (R)-3-bromo-3-methylhexane + CH₃OH

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