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

Previous problemNext problem

1:15 minutes

Problem 56a

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)

Verified step by step guidance

Step 1: Identify the reactant and product. The reactant is a tertiary alkyl chloride, and the product is a carbocation along with a chloride ion. This suggests an SN1 reaction mechanism.

Step 2: Recognize that the bond between the carbon atom and the chlorine atom will break heterolytically. This means the electrons in the bond will move entirely to the chlorine atom, forming a chloride ion (Cl⁻).

Step 3: Use curved arrow notation to show the movement of electrons. Draw an arrow starting from the bond between the carbon and chlorine atoms and pointing toward the chlorine atom. This represents the bond cleavage.

Step 4: After the bond breaks, the carbon atom becomes positively charged, forming a carbocation. The chlorine atom gains the pair of electrons, resulting in a chloride ion with a full octet.

Step 5: Ensure that lone pairs are drawn on the chlorine atom in the product to indicate its complete octet. Verify that the carbocation is correctly represented with a positive charge on the central carbon atom.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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 illustrate the movement of electrons during chemical reactions. In these diagrams, arrows represent the flow of electron pairs, indicating how bonds are formed or broken. Understanding this mechanism is crucial for predicting the products of reactions and visualizing the transition states involved.

Lone Pairs

Lone pairs are pairs of valence electrons that are not involved in bonding and are localized on an atom. They play a significant role in determining the reactivity and geometry of molecules. In arrow-pushing mechanisms, it is important to represent lone pairs accurately, as they can participate in reactions or influence the stability of intermediates.

Electrophiles and Nucleophiles

Electrophiles are electron-deficient species that seek electrons, while nucleophiles are electron-rich species that donate electrons. In the context of the provided reaction, recognizing which species acts as the electrophile and which as the nucleophile is essential for understanding the direction of electron flow and the formation of the product.

Watch next

Master How to tell if a molecule will be reactive or not. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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

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

(iv)

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)

Textbook Question

Identify the nucleophile and the electrophile in each of the following reactions.

(b)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

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)

Key Concepts

Arrow-Pushing Mechanism

Lone Pairs

Electrophiles and Nucleophiles

Watch next

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)