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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4:45 minutes

Problem 9

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?

Verified step by step guidance

Understand the context: The problem involves comparing the relative rates of reaction for cis and trans alkenes. Cis and trans isomers differ in their spatial arrangement, which can influence their reactivity due to steric and electronic effects.

Review the data in Table 22.2: Locate the relative rate of reaction for the cis alkene (E) in the table. This value will serve as a reference point for comparison with the trans alkene.

Consider steric effects: Cis alkenes typically have substituents on the same side of the double bond, leading to greater steric hindrance. Trans alkenes, with substituents on opposite sides, generally experience less steric hindrance, which can affect their reactivity.

Analyze electronic effects: The spatial arrangement of substituents in cis and trans alkenes can also influence the stability of the transition state during the reaction. Trans alkenes often have a more favorable transition state due to reduced steric strain.

Predict the relative rate: Based on the steric and electronic considerations, hypothesize whether the trans alkene will react faster or slower than the cis alkene. Use the relative rate of the cis alkene as a benchmark to estimate the relative rate of the trans alkene.

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Key Concepts

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

Cis and Trans Isomerism

Cis and trans isomerism refers to the geometric isomers of alkenes, where 'cis' indicates that substituents are on the same side of the double bond, while 'trans' indicates they are on opposite sides. This spatial arrangement affects the physical and chemical properties of the compounds, including their reactivity.

Reaction Mechanisms of Alkenes

The reaction mechanisms of alkenes often involve electrophilic addition, where the double bond acts as a nucleophile. The stability of the intermediate carbocation formed during the reaction can influence the rate of reaction, with more substituted alkenes typically reacting faster due to greater stability.

Steric Hindrance

Steric hindrance refers to the repulsion between bulky groups in a molecule that can impede reactions. In the case of alkenes, the spatial arrangement of substituents can affect how easily reactants approach the double bond, influencing the overall rate of reaction for cis versus trans isomers.

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Related Practice

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.)

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.

Textbook Question

In a reaction in which reactant A is in equilibrium with product B at 25 °C, what relative amounts of A and B are present at equilibrium if ∆G° at 25 °C is

a. 2.72 kcal/mol?

b. 0.65 kcal/mol?

Textbook Question

In a reaction in which reactant A is in equilibrium with product B at 25 °C, what relative amounts of A and B are present at equilibrium if ∆G° at 25 °C is

c. -2.72 kcal/mol?

d. -0.65 kcal/mol?

Textbook Question

The reaction of chloromethane with hydroxide ion at 30 °C has a ΔG° value of −21.7 kcal/mol. What is the equilibrium constant for the reaction?

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