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

Reaction Mechanism

Organic Chemistry

3. Acids and Bases

Reaction Mechanism

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7:21 minutes

Problem 59d

Textbook Question

Identify the arrow types that are shown in each of these arrow-pushing mechanisms.
(iv)

Verified step by step guidance

Step 1: Analyze the first arrow labeled (a). This arrow represents the movement of electrons from the lone pair on the oxygen atom to form a double bond with the carbon atom. This is an example of a 'lone pair to bond' arrow.

Step 2: Examine the second arrow labeled (b). This arrow shows the movement of electrons from the carbon-chlorine bond to the chlorine atom, breaking the bond. This is an example of a 'bond to lone pair' arrow.

Step 3: Look at the third arrow labeled (c). This arrow represents the movement of electrons from the lone pair on the hydroxide ion (HO⁻) to the carbon atom, forming a bond. This is an example of a 'lone pair to bond' arrow.

Step 4: Observe the fourth arrow labeled (d). This arrow shows the movement of electrons from the carbon-chlorine bond to the chlorine atom, breaking the bond. This is another example of a 'bond to lone pair' arrow.

Step 5: Summarize the mechanism. The arrow-pushing mechanism involves electron movement to form and break bonds, specifically 'lone pair to bond' and 'bond to lone pair' types of arrows, facilitating the substitution reaction.

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Key Concepts

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

Arrow-Pushing Mechanism

Arrow-pushing mechanisms are a way to represent the movement of electrons during chemical reactions. In these diagrams, arrows indicate the direction of electron flow, showing how bonds are formed or broken. Understanding these mechanisms is crucial for predicting the outcome of reactions and for grasping the underlying principles of organic chemistry.

Nucleophiles and Electrophiles

Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept electron pairs. In arrow-pushing mechanisms, nucleophiles typically attack electrophiles, leading to bond formation. Recognizing these roles is essential for analyzing reaction pathways and understanding how different reagents interact.

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. They help in understanding the stability and reactivity of intermediates in a reaction. In arrow-pushing mechanisms, resonance can explain the movement of electrons and the formation of stable products, making it a key concept in organic reaction mechanisms.

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Related Practice

Textbook Question

Each of these compounds can react as an electrophile. In each case, use curved arrows to show how the electrophile would react with the strong nucleophile sodium ethoxide, Na⁺ ⁻OCH₂CH₃.

b. NH₄⁺

Textbook Question

Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.

(d)

Textbook Question

Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.

(b)

Textbook Question

Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.

(a)

Textbook Question

Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Only one arrow is necessary in each reaction. [Don't forget to draw in the lone pairs on this and the next two assessments.]

(a)

Textbook Question

Suggest an arrow-pushing mechanism for each of the following acid–base reactions

(c)

Textbook Question

Would you expect the following species to be electrophiles or nucleophiles? Some may be both. Explain your answer.

(h)

Textbook Question

Would you expect the following species to be electrophiles or nucleophiles? Some may be both. Explain your answer.

(c)

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Identify the arrow types that are shown in each of these arrow-pushing mechanisms. (iv)

Key Concepts

Arrow-Pushing Mechanism

Nucleophiles and Electrophiles

Resonance Structures

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Identify the arrow types that are shown in each of these arrow-pushing mechanisms.
(iv)