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

E2 Mechanism

Organic Chemistry

8. Elimination Reactions

E2 Mechanism

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Problem 68g,h

Textbook Question

What are the products of the following reactions?
g.
h.

Verified step by step guidance

Step 1: For reaction (g), recognize that CH3OH (methanol) is in excess and CH3O- (methoxide ion) is present. This suggests a nucleophilic substitution or esterification reaction. Analyze the structure of the starting material to determine the reactive sites.

Step 2: Identify the functional groups in the starting material. If the starting material contains a leaving group (e.g., halide or tosylate), methoxide ion (CH3O-) will act as a nucleophile and replace the leaving group. If the starting material contains a carbonyl group, methanol may react to form an ester.

Step 3: Write the mechanism for the reaction. For nucleophilic substitution, show the attack of CH3O- on the electrophilic carbon attached to the leaving group, followed by the departure of the leaving group. For esterification, show the reaction of methanol with the carbonyl group, forming an ester and releasing a byproduct (e.g., water).

Step 4: For reaction (h), recognize that (CH3C=O)2O is acetic anhydride. Heating (Δ) acetic anhydride typically leads to its reaction with nucleophiles or decomposition. Analyze the conditions to predict the products.

Step 5: Write the mechanism for the reaction of acetic anhydride under heat. If no nucleophile is present, acetic anhydride may decompose into acetic acid and ketene. If a nucleophile is present, acetic anhydride may react to form an ester or amide, depending on the nucleophile.

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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, such as methanol (CH3OH), attacks an electrophilic carbon atom, resulting in the replacement of a leaving group. In the given reaction, methanol acts as a nucleophile, forming a methoxy group (CH3O-) as a product when it reacts with an appropriate electrophile.

Acid Anhydrides

Acid anhydrides, like (CH3C=O)2O, are compounds formed from two acyl groups and are reactive intermediates in organic synthesis. When heated (Δ), they can undergo reactions such as hydrolysis or nucleophilic acyl substitution, leading to the formation of carboxylic acids or esters, depending on the nucleophile involved.

Reaction Conditions

Reaction conditions, including temperature, solvent, and the presence of catalysts, significantly influence the outcome of organic reactions. For instance, the use of excess methanol and heat in the reactions can drive the formation of specific products, such as esters or ethers, by favoring the nucleophilic attack and stabilizing the transition states.

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Related Practice

Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following E2 reactions.

(a)

Textbook Question

Suggest a mechanism for the following elimination reactions.

(c)

Textbook Question

Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.

(a)

Textbook Question

When a secondary haloalkane is treated with sodium ethoxide in ethanol, we predict alkene formation over ether formation. How did we make this determination?

Textbook Question

Which compound has the greatest rate of hydrolysis at pH = 3.5: benzamide, o-carboxybenzamide, o-formylbenzamide, or o-hydroxybenzamide?

Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following E2 reactions.

(b)

Textbook Question

Identify the bonds that break and form in the following elimination reactions.

(b)

Textbook Question

If a quaternary ammonium ion can undergo an elimination reaction with a strong base, why can’t a protonated tertiary amine undergo the same reaction?

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