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

6. Thermodynamics and Kinetics

Gibbs Free Energy

Organic Chemistry

6. Thermodynamics and Kinetics

Gibbs Free Energy

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Problem 29b

Textbook Question

For the following acid–base reactions studied in Assessment 5.25, draw a likely transition state. Be sure to indicate in your drawing the degree to which bonds are broken or formed.
(b)

Verified step by step guidance

Step 1: Identify the acid and base in the reaction. In the given reaction, the molecule with the hydroxyl group (-OH) acts as the acid, donating a proton (H⁺), while the molecule with the amine group (-NH₂) acts as the base, accepting the proton.

Step 2: Recognize the transition state. The transition state represents the intermediate structure where bonds are partially broken and formed. In this case, the O-H bond of the acid is partially broken, and the N-H bond of the base is partially formed.

Step 3: Draw the transition state. Represent the O-H bond as partially broken using a dashed line, and the N-H bond as partially formed using another dashed line. Indicate the movement of electrons with curved arrows: one arrow showing the lone pair on nitrogen attacking the hydrogen, and another arrow showing the bond between oxygen and hydrogen breaking.

Step 4: Include partial charges in the transition state. The oxygen atom will have a partial negative charge (δ⁻) due to the breaking of the O-H bond, and the nitrogen atom will have a partial positive charge (δ⁺) due to the formation of the N-H bond.

Step 5: Verify the transition state drawing. Ensure that the drawing accurately represents the intermediate structure with partial bonds and charges, and that it aligns with the acid-base reaction mechanism.

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Key Concepts

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

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. An acid donates a proton, while a base accepts it. Understanding the nature of acids and bases, including their strength and the concept of conjugate pairs, is essential for predicting the outcome of these reactions and drawing accurate transition states.

Transition States

A transition state represents a high-energy, unstable arrangement of atoms that occurs during the transformation from reactants to products. It is characterized by partially formed and broken bonds. Drawing a transition state requires an understanding of the molecular geometry and the changes in bonding that occur as the reaction progresses.

Bond Formation and Breaking

In chemical reactions, bonds between atoms are either formed or broken. The extent of bond formation and breaking can be depicted in a transition state diagram. Recognizing which bonds are involved and the degree to which they are altered is crucial for accurately representing the transition state and understanding the reaction mechanism.

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Related Practice

Textbook Question

For each pair of reactions, predict which will happen more quickly.

[For (a) and (b), think about the stability of the bases involved.]

(a)

Textbook Question

For the following equilibrium processes and the corresponding ∆G° , indicate whether you expect the equilibrium constant to be greater than, equal to, or less than 1. Justify your expectation in words.

(b)

Textbook Question

For the following acid–base reactions studied in Assessment 5.25, draw a likely transition state. Be sure to indicate in your drawing the degree to which bonds are broken or formed.

(a)

Textbook Question

For the following acid–base reactions studied in Assessment 5.25, draw a likely transition state. Be sure to indicate in your drawing the degree to which bonds are broken or formed.

Textbook Question

Calculate ∆G° for the conversion of “axial” methylcyclohexane to “equatorial” methylcyclohexane at 25 °C.

Textbook Question

Calculate the percentage of isopropylcyclohexane molecules that have the isopropyl substituent in an equatorial position at equilibrium. (Its ∆G° value at 25 °C is -2.1 kcal/mol.)

Textbook Question

The relative rate of reaction for the cis alkene (E) is given in Table 22.2. What do you expect the relative rate of reaction for the trans alkene to be?

Textbook Question

Explain why the half-life (the time it takes for one-half of the compound to be metabolized) of Xylocaine is longer than that of Novocaine.

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For the following acid–base reactions studied in Assessment 5.25, draw a likely transition state. Be sure to indicate in your drawing the degree to which bonds are broken or formed.(b)

Key Concepts

Acid-Base Reactions

Transition States

Bond Formation and Breaking

Watch next

For the following acid–base reactions studied in Assessment 5.25, draw a likely transition state. Be sure to indicate in your drawing the degree to which bonds are broken or formed.
(b)