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

3. Acids and Bases

Ranking Acidity

Organic Chemistry

3. Acids and Bases

Ranking Acidity

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2:06 minutes

Problem 20d,e,f

Textbook Question

For each of the following substituents, indicate whether it withdraws electrons inductively, donates electrons by hyperconjugation, withdraws electrons by resonance, or donates electrons by resonance.
d. NHCH₃
e. OCH₃
f. ⁺N(CH₃)₃

Verified step by step guidance

Step 1: Understand the four electronic effects mentioned in the problem: (1) Inductive electron withdrawal occurs when a substituent pulls electron density through sigma bonds due to its electronegativity. (2) Hyperconjugation involves the donation of electron density through overlap of sigma bonds with an adjacent empty or partially filled orbital. (3) Resonance electron withdrawal happens when a substituent withdraws electron density through delocalization of electrons via pi bonds. (4) Resonance electron donation occurs when a substituent donates electron density through delocalization of lone pairs or pi electrons into the conjugated system.

Step 2: Analyze the substituent in part (d). Determine if the substituent has electronegative atoms or groups that can withdraw electrons inductively, lone pairs that can participate in resonance donation, or pi systems that can withdraw electrons by resonance.

Step 3: Analyze the substituent in part (e). Follow the same process as in Step 2, identifying whether the substituent exhibits inductive withdrawal, hyperconjugation donation, resonance withdrawal, or resonance donation based on its structure and electronic properties.

Step 4: Analyze the substituent in part (f). Again, evaluate the substituent's ability to withdraw or donate electrons through inductive effects, hyperconjugation, or resonance mechanisms. Pay attention to the presence of electronegative atoms, lone pairs, or conjugated systems.

Step 5: Summarize the findings for each substituent (d, e, f) based on the analysis. Clearly indicate which electronic effect(s) each substituent exhibits, ensuring the reasoning aligns with the substituent's structure and electronic characteristics.

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Key Concepts

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

Inductive Effect

The inductive effect refers to the permanent polarization of a bond due to the electronegativity difference between atoms. Electronegative atoms or groups can withdraw electron density from adjacent atoms, leading to a decrease in electron density in the molecule. This effect diminishes with distance and is crucial for understanding how substituents influence the reactivity and stability of organic compounds.

Resonance Effect

The resonance effect involves the delocalization of electrons across multiple atoms in a molecule, which can stabilize the structure. Electron-donating groups can provide electron density through resonance, while electron-withdrawing groups can pull electron density away. Understanding resonance is essential for predicting the behavior of substituents in reactions and their impact on molecular stability.

Hyperconjugation

Hyperconjugation is a stabilizing interaction that occurs when electron density from a filled orbital (usually a sigma bond) interacts with an adjacent empty orbital (like a pi bond or a carbocation). This effect can lead to increased stability in certain molecular structures, particularly in carbocations, and is important for understanding how alkyl groups can donate electron density to positively charged centers.

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For each of the following substituents, indicate whether it withdraws electrons inductively, donates electrons by hyperconjugation, withdraws electrons by resonance, or donates electrons by resonance. d. NHCH3e. OCH3f. +N(CH3)3

Key Concepts

Inductive Effect

Resonance Effect

Hyperconjugation

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For each of the following substituents, indicate whether it withdraws electrons inductively, donates electrons by hyperconjugation, withdraws electrons by resonance, or donates electrons by resonance.
d. NHCH₃
e. OCH₃
f. ⁺N(CH₃)₃