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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5:35 minutes

Problem 27d

Textbook Question

Make models of the following compounds, and predict the products formed when they react with the strong bases shown.
(d)

Verified step by step guidance

Step 1: Identify the type of reaction. The presence of NaOH in acetone suggests that this is an E2 elimination reaction, which typically occurs with strong bases and favors anti-coplanar geometry.

Step 2: Analyze the structure of the substrate. The molecule is a bicyclic compound with a chlorine atom attached to a carbon. The hydrogen atom on the adjacent carbon is positioned anti-coplanar to the chlorine atom, which is a requirement for E2 elimination.

Step 3: Determine the leaving group and the proton to be abstracted. In this case, the chlorine atom is the leaving group, and the base (NaOH) will abstract the anti-coplanar hydrogen from the adjacent carbon.

Step 4: Predict the product of the elimination. The removal of the hydrogen and chlorine will result in the formation of a double bond between the two carbons involved in the elimination. The bicyclic structure will remain intact, but a new alkene will be formed.

Step 5: Consider stereochemistry and regioselectivity. Since anti-coplanar geometry is required, the elimination will occur in a specific direction dictated by the spatial arrangement of the substituents. Ensure the double bond is placed correctly in the bicyclic structure.

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Key Concepts

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

E2 Elimination Mechanism

The E2 elimination mechanism is a concerted reaction where a strong base abstracts a proton from a β-carbon while a leaving group departs from the α-carbon, resulting in the formation of a double bond. This mechanism requires the hydrogen and leaving group to be anti-coplanar, meaning they must be on opposite sides of the molecule, which facilitates the elimination process.

Anti-Coplanar vs. Syn-Coplanar

In E2 reactions, anti-coplanar arrangements are preferred because they allow for optimal orbital overlap during the transition state, leading to more stable products. Syn-coplanar arrangements, where the hydrogen and leaving group are on the same side, are less common and typically occur when free rotation around the bond is restricted, such as in cyclic compounds.

Role of Strong Bases

Strong bases, like NaOH, are crucial in E2 reactions as they effectively deprotonate the β-hydrogen, facilitating the elimination of the leaving group. The choice of solvent, such as acetone, can also influence the reaction pathway and product distribution, as polar aprotic solvents can stabilize the transition state and enhance the reactivity of the base.

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Textbook Question

Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.

a. 1−bromohexane + sodium ethoxide in ethanol

Textbook Question

Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.

b. 2−chlorohexane + NaOCH₃ in methanol

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When (±)−2,3−dibromobutane reacts with potassium hydroxide, some of the products are (2S,3R)-3-bromobutan-2-ol and its enantiomer and trans-2-bromobut-2-ene. Give mechanisms to account for these products.

Textbook Question

Make models of the following compounds, and predict the products formed when they react with the strong bases shown.

Textbook Question

Propose mechanisms for the following reactions. Additional products may be formed, but your mechanism only needs to explain the products shown.

(c)

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.

(b)

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.

(c)

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.

(d)

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Make models of the following compounds, and predict the products formed when they react with the strong bases shown.(d)

Key Concepts

E2 Elimination Mechanism

Anti-Coplanar vs. Syn-Coplanar

Role of Strong Bases

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Make models of the following compounds, and predict the products formed when they react with the strong bases shown.
(d)