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

4. Alkanes and Cycloalkanes

Cis vs Trans

Organic Chemistry

4. Alkanes and Cycloalkanes

Cis vs Trans

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2:57 minutes

Problem 9

Textbook Question

Tamoxifen slows the growth of some breast tumors by binding to estrogen receptors. Is tamoxifen an E or a Z isomer?

Verified step by step guidance

Step 1: Identify the double bond in tamoxifen's structure that can exhibit E/Z isomerism. In the provided structure, the double bond is located between the central carbon and the phenyl group attached to the chlorine atom.

Step 2: Assign priorities to the groups attached to the double bond using the Cahn-Ingold-Prelog priority rules. The groups attached to the double bond are the phenyl group with the chlorine atom and the other phenyl group. Consider atomic numbers and connectivity to determine priority.

Step 3: Determine the spatial arrangement of the higher-priority groups. If the higher-priority groups are on opposite sides of the double bond, the isomer is E. If they are on the same side, the isomer is Z.

Step 4: Analyze the structure provided in the image. Observe the orientation of the phenyl groups relative to the double bond to decide whether tamoxifen is an E or Z isomer.

Step 5: Conclude the isomer type based on the spatial arrangement observed in the structure. Ensure the analysis aligns with the priority rules and the geometry of the molecule.

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Key Concepts

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

Isomerism

Isomerism refers to the phenomenon where two or more compounds have the same molecular formula but different structural arrangements. In organic chemistry, isomers can be classified into structural isomers and stereoisomers, the latter including geometric isomers like cis and trans. Understanding isomerism is crucial for determining the properties and reactivity of compounds, such as tamoxifen.

Cis-Trans Isomerism

Cis-trans isomerism is a type of stereoisomerism that occurs due to restricted rotation around a double bond or a ring structure. In this context, 'cis' refers to substituents being on the same side of the double bond, while 'trans' indicates they are on opposite sides. This distinction can significantly affect the physical and chemical properties of the molecules, including their biological activity.

Estrogen Receptors

Estrogen receptors are proteins that bind estrogen and mediate its effects in the body, playing a crucial role in the growth and regulation of breast tissue. Tamoxifen acts as a selective estrogen receptor modulator (SERM), meaning it can block or activate these receptors depending on the tissue type. Understanding the interaction between tamoxifen and estrogen receptors is essential for grasping its therapeutic role in breast cancer treatment.