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

19. Reactions of Aromatics: EAS and Beyond

Birch Reduction

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Birch Reduction

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Multiple Choice

Predict the major product from the Birch Reduction

Structure of the first product from the Birch Reduction with CF3 group.

Structure of the second product from the Birch Reduction with CF3 group.

Structure of the third product from the Birch Reduction with CF3 group.

Structure of the fourth product from the Birch Reduction with CF3 group.

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Verified step by step guidance

Identify the reaction type: The Birch reduction is a reaction that reduces aromatic rings to non-conjugated dienes using alkali metals (such as sodium) in liquid ammonia with an alcohol (such as t-butanol) as a proton source.

Analyze the starting material: The given compound is a naphthalene derivative with a trifluoromethyl (CF3) group attached. The Birch reduction will affect the aromatic ring system.

Determine the regioselectivity: In Birch reduction, electron-withdrawing groups (like CF3) direct the reduction to occur at the positions ortho and para to the substituent, avoiding the position directly adjacent to the substituent.

Predict the product structure: The reduction will result in the formation of a non-conjugated diene. The double bonds will be placed in positions that are not directly adjacent to the CF3 group, typically resulting in a 1,4-cyclohexadiene structure.

Consider the options: Among the given options, identify the structure that matches the expected product of the Birch reduction, considering the placement of the double bonds relative to the CF3 group.