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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6:58 minutes

Problem 72c

Textbook Question

Assign relative priorities to each set of substituents:
c. -C(=O)CH₃, -CH=CH₂, -Cl, -C=N

Verified step by step guidance

Step 1: Understand the Cahn-Ingold-Prelog (CIP) priority rules. These rules are used to assign priorities based on atomic number, connectivity, and bonding. The higher the atomic number of the directly attached atom, the higher the priority. If the directly attached atoms are the same, move outward to the next set of atoms and compare.

Step 2: Analyze the substituents individually. For -C(=O)CH3, the carbon is double-bonded to oxygen, which has a higher atomic number than hydrogen or carbon. This increases its priority. For -CH=CH2, the carbon is double-bonded to another carbon, which is less electronegative than oxygen. For -Cl, chlorine has a high atomic number (17), giving it a high priority. For -C=N, the carbon is triple-bonded to nitrogen, which has an atomic number of 7, higher than carbon but lower than chlorine.

Step 3: Compare the substituents based on the atomic number of the directly attached atoms. Chlorine (-Cl) has the highest atomic number (17), so it will have the highest priority. Oxygen in -C(=O)CH3 has an atomic number of 8, which is higher than nitrogen in -C=N (atomic number 7) and carbon in -CH=CH2 (atomic number 6).

Step 4: Consider the bonding and connectivity for the remaining substituents. For -C(=O)CH3, the carbon is double-bonded to oxygen, which increases its priority over -C=N, where the carbon is triple-bonded to nitrogen. Finally, -CH=CH2 has the lowest priority because it is only bonded to carbons and hydrogens.

Step 5: Assign the relative priorities based on the analysis: 1) -Cl, 2) -C(=O)CH3, 3) -C=N, 4) -CH=CH2.

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Key Concepts

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

Substituent Priority in Organic Chemistry

In organic chemistry, substituents attached to a carbon chain can be prioritized based on their functional groups and the rules established by the Cahn-Ingold-Prelog (CIP) priority system. This system assigns higher priority to substituents based on atomic number and connectivity, which is crucial for determining stereochemistry and reactivity in organic compounds.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the question, the substituents -C(=O)CH3 (an acyl group), -CH=CH2 (an alkene), -Cl (a halogen), and -C=N (a nitrile) represent different functional groups, each with distinct properties that influence their priority.

Electronegativity and Reactivity

Electronegativity refers to the tendency of an atom to attract electrons in a bond. In assigning priorities to substituents, electronegativity plays a role, as more electronegative atoms (like Cl) can influence the reactivity and stability of the molecule. Understanding how electronegativity affects the behavior of substituents is essential for predicting the outcomes of chemical reactions.

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