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

10. Addition Reactions

Carbene

Organic Chemistry

10. Addition Reactions

Carbene

Previous problemNext problem

5:13 minutes

Problem 28c

Textbook Question

Show how you would accomplish each of the following synthetic conversions.
(c)

Verified step by step guidance

Step 1: Convert cyclohexanol to cyclohexene by performing an acid-catalyzed dehydration reaction. Use a strong acid like H2SO4 or H3PO4 to remove water and form the double bond.

Step 2: Perform a halogenation reaction on cyclohexene. React cyclohexene with Cl2 in an inert solvent like CCl4 to add two chlorine atoms across the double bond, forming 1,2-dichlorocyclohexane.

Step 3: Ensure stereochemistry is considered during the halogenation step. The addition of Cl2 will proceed via a cyclic halonium ion intermediate, leading to anti-addition of chlorine atoms.

Step 4: Verify the product structure to ensure it matches the desired 1,2-dichlorocyclohexane with the correct stereochemistry.

Step 5: Purify the product using techniques like distillation or recrystallization, if necessary, to isolate the final compound.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the context of converting cyclohexanol to a dichlorinated product, the hydroxyl group (-OH) of cyclohexanol can be replaced by chlorine atoms through a nucleophilic substitution mechanism, typically involving reagents like thionyl chloride (SOCl2) or phosphorus trichloride (PCl3).

Reactivity of Alcohols

Alcohols, such as cyclohexanol, are reactive compounds that can undergo various transformations. The hydroxyl group in alcohols can be converted into better leaving groups, facilitating substitution reactions. Understanding the reactivity of alcohols is crucial for predicting the outcome of synthetic conversions, including the formation of chlorinated derivatives.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the conversion of cyclohexanol to a dichlorinated product, the stereochemistry of the resulting compound is important, as the position of the chlorine atoms can lead to different isomers. Recognizing the stereochemical implications of reactions helps in understanding the properties and reactivity of the final product.

Watch next

Master General properties of cyclopropanation. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(g)

Textbook Question

Propose mechanisms consistent with the following reactions.

(d)

Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

m. CHBr₃ and 50% aq. NaOH

Textbook Question

When it is strongly heated, ethyl diazoacetate decomposes to give nitrogen gas and a carbene. Draw a Lewis structure of the carbene.

Textbook Question

In addition to radicals, anions, and cations, a fourth class of reactive intermediates is carbenes. A neutral species, the simplest carbene has a molecular formula of CH₂.

(f) Cyclopropanation of (E)- and (Z)-3-methylhex-3-ene gives two different products. Rationalize this outcome.

Textbook Question

Suggest a mechanism for the reaction shown in Figure 16.30 using IZnCH₂I as the cyclopropanating reagent.

Textbook Question

Two chemists at Dupont found that ICH₂ZnI is better than diazomethane at converting a C=C bond to a cylcopropane ring. Propose a mechanism for the reaction, now known as the Simmons–Smith reaction in their honor.

Multiple Choice

What is the formal charge on the carbon of the following carbene?

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

Show how you would accomplish each of the following synthetic conversions. (c)

Key Concepts

Nucleophilic Substitution

Reactivity of Alcohols

Stereochemistry

Watch next

Show how you would accomplish each of the following synthetic conversions.
(c)