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

11. Radical Reactions

Free Radical Halogenation

Organic Chemistry

11. Radical Reactions

Free Radical Halogenation

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2:01 minutes

Problem 43(1)a,b

Textbook Question

For each alkane,
1. draw all the possible monochlorinated derivatives.
a. Cyclopentane
b. Methylcyclopentane

Verified step by step guidance

Step 1: Understand the concept of monochlorination. Monochlorination involves replacing one hydrogen atom in an alkane with a chlorine atom, resulting in a single chlorinated product. For each unique hydrogen environment in the molecule, a different monochlorinated derivative can be formed.

Step 2: Analyze the structure of cyclopentane. Cyclopentane is a cyclic alkane with the molecular formula C5H10. All the hydrogen atoms in cyclopentane are equivalent due to its symmetrical structure. Therefore, replacing any one hydrogen atom with a chlorine atom will result in only one unique monochlorinated derivative.

Step 3: Analyze the structure of methylcyclopentane. Methylcyclopentane is a substituted cycloalkane with a methyl group (-CH3) attached to the cyclopentane ring. The molecular formula is C6H12. In this case, the hydrogens on the ring and the hydrogens on the methyl group are in different environments. Identify the unique hydrogen environments: (a) hydrogens on the methyl group, (b) hydrogens on the carbons adjacent to the methyl group, and (c) hydrogens on the other carbons in the ring.

Step 4: Draw the monochlorinated derivatives for methylcyclopentane. Replace one hydrogen atom from each unique environment identified in Step 3 with a chlorine atom. This will result in multiple unique monochlorinated derivatives, each corresponding to a different hydrogen environment.

Step 5: Verify the uniqueness of each derivative. Ensure that no two derivatives are identical by checking for symmetry in the molecule. For example, if two hydrogens are in equivalent positions due to the molecule's symmetry, replacing either of them will result in the same product.

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Key Concepts

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

Alkanes

Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, connected by single bonds. They follow the general formula CnH2n+2, where 'n' is the number of carbon atoms. Understanding the structure and properties of alkanes is essential for predicting their reactivity, particularly in substitution reactions like chlorination.

Chlorination Reaction

Chlorination is a type of substitution reaction where a hydrogen atom in an alkane is replaced by a chlorine atom. This process typically involves free radical mechanisms, initiated by heat or light, leading to the formation of monochlorinated derivatives. Recognizing the potential sites for chlorination on cyclic and branched alkanes is crucial for drawing all possible derivatives.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical properties. In the case of chlorinated derivatives, different stereoisomers can form due to the presence of chiral centers or different spatial orientations. Understanding stereochemistry is important for accurately representing and naming the various monochlorinated products of cyclopentane and methylcyclopentane.

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Related Practice

Textbook Question

When exactly 1 mole of methane is mixed with exactly 1 mole of chlorine and light is shone on the mixture, a chlorination reaction occurs. The products are found to contain substantial amounts of di-, tri-, and tetrachloromethane, as well as unreacted methane.

b. How would you run this reaction to get a good conversion of methane to CH₃Cl? Of methane to CCl₄?

Textbook Question

Write the propagation steps leading to the formation of dichloromethane (CH₂Cl₂) from chloromethane.

Textbook Question

Each of the following proposed mechanisms for the free-radical chlorination of methane is wrong. Explain how the experimental evidence disproves each mechanism.

Textbook Question

b. Calculate ΔH° for each step in this reaction.

c. Calculate the overall value of ΔH° for this reaction.

Textbook Question

For each alkane,

2. determine whether free-radical chlorination would be a good way to make any of these monochlorinated derivatives. Will the reaction give mostly one major product?

a. Cyclopentane

b. Methylcyclopentane

Textbook Question

Explain why free-radical halogenation usually gives mixtures of products.

Textbook Question

How many dibrominated products could each of the compounds form if stereoisomers are included?

Textbook Question

The following compounds have the same molecular formula as benzene. How many monobrominated products could each form?

1. HC≡CC≡CCH₂CH₃

2. CH₂=CHC≡CCH=CH₂

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