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 29a

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)

Verified step by step guidance

Step 1: Identify the reactants and products in the given acid-base reaction. The reactants are tert-butoxide ion (\( (CH_3)_3CO^- \)) and isopropanol (\( (CH_3)_2CHOH \)), while the products are isopropoxide ion (\( (CH_3)_2CHO^- \)) and tert-butanol (\( (CH_3)_3COH \)).

Step 2: Recognize the type of reaction. This is a proton transfer reaction, where the tert-butoxide ion acts as a base and abstracts a proton (H⁺) from isopropanol, forming the isopropoxide ion and tert-butanol.

Step 3: Understand the transition state. The transition state represents the point at which the proton is partially transferred from the isopropanol to the tert-butoxide ion. At this stage, the O-H bond in isopropanol is partially broken, and the O-H bond in tert-butanol is partially formed.

Step 4: Draw the transition state. Use dashed lines to indicate the partial bonds being formed and broken. For example, the O-H bond in isopropanol should be shown as a dashed line to indicate partial breaking, and the O-H bond in tert-butanol should also be shown as a dashed line to indicate partial formation. Include partial charges on the oxygen atoms to reflect the electron density changes during the transition state.

Step 5: Label the transition state. Clearly indicate the transition state with a double dagger symbol (‡) and ensure that all atoms and bonds are properly represented. Highlight the flow of electrons using curved arrows to show the movement of the proton from isopropanol to tert-butoxide.

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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 acid-base pairs, is essential for predicting the outcome of these reactions and drawing accurate transition states.

Transition States

A transition state is a high-energy, unstable arrangement of atoms that occurs during the transformation of reactants into products. It represents the point of maximum energy along the reaction pathway. Drawing a transition state requires an understanding of bond formation and breaking, as well as the geometry of the reacting species at this critical moment.

Bond Formation and Breaking

In chemical reactions, bonds between atoms are either formed or broken as reactants convert to products. The extent of bond breaking and forming can be depicted in a transition state diagram, which illustrates the changes in bond lengths and angles. Recognizing how these changes correlate with the energy profile of the reaction is crucial for accurately representing the transition state.

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Related Practice

Textbook Question

For the following equilibrium processes and the corresponding ∆G°, calculate (i) K_eq and (ii) the % composition of the equilibrium mixture (% reactants, % products) at 298 K.

(a)

Textbook Question

For the following equilibrium processes and the corresponding ∆G°, calculate (i) K_eq and (ii) the % composition of the equilibrium mixture (% reactants, % products) at 298 K.

(b)

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.

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)

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.)

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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.(a)

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.
(a)