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

7. Substitution Reactions

Substitution Comparison

Organic Chemistry

7. Substitution Reactions

Substitution Comparison

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6:29 minutes

Problem 8a

Textbook Question

What stereoisomers does the following reaction form?

Verified step by step guidance

Step 1: Analyze the given structure. The molecule contains a secondary alcohol (-OH group) attached to a chiral carbon. The reaction involves HCl and heat, which suggests a substitution reaction where the hydroxyl group is replaced by a chloride ion.

Step 2: Understand the mechanism. The reaction likely proceeds via an SN1 mechanism due to the secondary alcohol and the presence of heat. In an SN1 reaction, the hydroxyl group is protonated by HCl, forming water as a leaving group. This generates a carbocation intermediate.

Step 3: Consider the stereochemistry of the carbocation intermediate. The carbocation formed is planar (sp2 hybridized), meaning it can be attacked by the chloride ion from either side, leading to the formation of two stereoisomers (R and S configurations).

Step 4: Predict the products. Since the chloride ion can attack from either side of the planar carbocation, the reaction forms a racemic mixture of the two stereoisomers.

Step 5: Summarize the stereoisomers formed. The reaction produces two stereoisomers: one with the R configuration and one with the S configuration at the chiral center where the chloride is attached.

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Key Concepts

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

Stereoisomerism

Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of those atoms. This can lead to different physical and chemical properties. The two main types of stereoisomers are enantiomers, which are non-superimposable mirror images, and diastereomers, which are not mirror images of each other.

Chirality

Chirality is a property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. A chiral center, typically a carbon atom bonded to four different substituents, is crucial for the formation of enantiomers. Understanding chirality is essential for predicting the stereoisomers produced in a reaction, as it influences the spatial arrangement of atoms.

Reaction Mechanism

A reaction mechanism describes the step-by-step process by which reactants are converted into products, including the formation and breaking of bonds. It provides insight into the intermediates and transition states involved in the reaction. Analyzing the mechanism is vital for determining the stereochemical outcomes, as it can reveal how stereocenters are created or altered during the reaction.

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Related Practice

Textbook Question

Provide a mechanism for the following S_N1 reactions that feature a rearrangement.

(b)

Textbook Question

Suggest a mechanism for the following substitution reactions.

(c)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vii) HCl; (viii) HBr; If no reaction occurs, write 'no reaction.'

(o)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions:(vii) HCl; (viii) HBr If no reaction occurs, write 'no reaction.'

(k)

Textbook Question

When tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether.

a. What happens to the reaction rate if the concentration of ethanol is doubled?

Textbook Question

Explain the difference in reactivity between CH₃O⁺H₂ and CH₃OH in a nucleophilic substitution reaction. (The pK_a of H₃O⁺ is −1.7.)