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

Energy Diagram

Organic Chemistry

6. Thermodynamics and Kinetics

Energy Diagram

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5:05 minutes

Problem 3

Textbook Question

Given that A is more stable than B, draw a reaction coordinate diagram that rationalizes the fact that A forms more quickly than B in the following reaction.

Verified step by step guidance

Understand the problem: The reaction coordinate diagram is a graphical representation of the energy changes during a chemical reaction. Since A forms more quickly than B, this suggests that the activation energy (Ea) for forming A is lower than that for forming B. Additionally, A is more stable than B, meaning A has a lower final energy than B.

Step 1: Draw the x-axis and y-axis of the reaction coordinate diagram. Label the x-axis as 'Reaction Progress' and the y-axis as 'Energy'.

Step 2: Represent the starting material (reactants) as a point on the y-axis at a certain energy level. This will be the same starting point for both pathways leading to A and B.

Step 3: Draw two curves starting from the reactants. The curve leading to A should have a lower peak (lower activation energy) compared to the curve leading to B. This reflects the fact that A forms more quickly than B.

Step 4: End the curve for A at a lower energy level than the curve for B. This indicates that A is more stable than B, as it has a lower final energy.

Step 5: Label the activation energy (Ea) for both pathways and the relative energy levels of A and B. Clearly indicate that the pathway to A has a lower Ea and a lower final energy compared to the pathway to B.

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Key Concepts

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

Reaction Coordinate Diagram

A reaction coordinate diagram is a graphical representation that illustrates the energy changes during a chemical reaction. It plots the potential energy of the reactants and products against the progress of the reaction. The diagram typically shows the transition states and intermediates, helping to visualize the energy barriers that must be overcome for the reaction to proceed.

Stability of Compounds

The stability of a compound refers to its tendency to remain in its current state without undergoing change. In organic chemistry, stability can be influenced by factors such as molecular structure, resonance, sterics, and electronic effects. A more stable compound, like A in this case, has lower energy and is less likely to react compared to a less stable compound, like B.

Activation Energy

Activation energy is the minimum energy required for a reaction to occur. It represents the energy barrier that reactants must overcome to form products. In the context of the reaction between A and B, if A has a lower activation energy compared to B, it will form more quickly, as fewer energy inputs are needed to initiate the reaction leading to A.

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Related Practice

Textbook Question

Draw a reaction coordinate diagram, making sure to label reactants (R), products (P), intermediates (I), transition states (‡), activation energies ( E_a) , and ∆G°, for each of the following.

(a) an exothermic, one-step reaction

Textbook Question

Draw a reaction coordinate diagram for the reaction. (Hint: An alkyl halide is more stable than an alkene.)

Textbook Question

Draw an approximate reaction-energy diagram showing the curves for the two possible pathways for ionic addition of HBr to 1-methylcyclohexene. (a) Formation of the major product, 1-bromo-1-methylcyclohexane, and (b) formation of the minor product, 1-bromo-2-methylcyclohexane. Point out how these curves show that 1-bromo-1-methylcyclohexane should be formed faster.

Textbook Question

On a single graph, draw the reaction coordinate diagram for the addition of one equivalent of HBr to 2-methyl-1,3-pentadiene and for the addition of one equivalent of HBr to 2-methyl-1,4-pentadiene. Which reaction is faster?

Textbook Question

Draw a reaction coordinate diagram for the following transformation. Label all product, intermediates, and substrates.

Textbook Question

For each of the reaction coordinate diagrams shown, (i) indicate the number of steps in the reaction, (ii) label the intermediates, (iii) identify the rate-determining step, and (iv) tell whether K_eq is greater than, less than, or equal to zero.

(a)

Textbook Question

Draw a reaction coordinate diagram, making sure to label reactants (R), products (P), intermediates (I), transition states (‡), activation energies ( E_a) , and ∆G°, for each of the following.

(d) a slightly exothermic, three-step reaction where the third step is rate-determining.

Textbook Question

The alkyl carbocation is estimated to be 15 kcal/mol more stable than the alkenyl carbocation. If this is also the difference in the energies of the transition state leading to each, what is the expected rate difference?

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