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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1:18 minutes

Problem 46c

Textbook Question

Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.
(c)

Verified step by step guidance

Step 1: Begin with cyclohexane as the starting material. Cyclohexane is a saturated hydrocarbon with no functional groups, so the first step is to introduce a functional group that can be further modified.

Step 2: Perform a free radical halogenation reaction using bromine (Br₂) and light (hv) to introduce a bromine atom onto the cyclohexane ring. This will yield bromocyclohexane.

Step 3: Convert bromocyclohexane into cyclohexyl cyanide by performing a nucleophilic substitution reaction (SN2). Use sodium cyanide (NaCN) as the nucleophile in an appropriate solvent, such as DMSO, to replace the bromine atom with a cyano group (-CN).

Step 4: Ensure the reaction conditions are optimized for SN2 substitution, as steric hindrance in cyclohexane is minimal, allowing for efficient substitution.

Step 5: Purify the product, cyclohexyl cyanide, using standard organic purification techniques such as distillation or recrystallization, depending on the physical properties of the compound.

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Key Concepts

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

Cyclohexane Structure

Cyclohexane is a six-membered carbon ring with the molecular formula C6H12. It is a saturated hydrocarbon, meaning it contains only single bonds between carbon atoms. Understanding its structure is crucial for predicting reactivity and the types of reactions it can undergo, such as substitution or elimination.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule with a nucleophile. In the context of cyclohexane, the introduction of a cyanide group (CN) typically occurs through a nucleophilic substitution mechanism, where the nucleophile attacks a carbon atom, leading to the formation of a new bond.

Functional Group Transformation

Functional group transformation refers to the process of converting one functional group into another within a molecule. In this case, transforming cyclohexane into a compound with a cyanide group involves understanding how to manipulate the existing structure to introduce new functional groups, which is essential for synthesizing desired organic compounds.

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Related Practice

Textbook Question

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

a. butan-1-ol

Textbook Question

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

b. 1-fluorobutane

Textbook Question

A solution of pure (S)-2-iodobutane ([α] = +15.90°) in acetone is allowed to react with radioactive iodide, ¹³¹I^–, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°.

b. What does this result suggest about the mechanism of the reaction of 2-iodobutane with iodide ion?

Textbook Question

Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below. In each case, explain what unwanted reactions might produce undesirable impurities in the product.

Textbook Question

Alkylbenzyldimethyl ammonium chloride is a leave-on skin antiseptic used to treat such things as cuts and cold sores. It is also the antiseptic in many hand sanitizers. It is actually a mixture of compounds that differ in the number of carbons (any even number between 8 and 18) in the alkyl group. Show three different sets of reagents (each set composed of an alkyl chloride and an amine) that can be used to synthesize the alkylbenzyldimethyl ammonium chloride shown here.

Textbook Question

Which reaction in each of the following pairs takes place more rapidly? (EtOH is ethyl alcohol; Et₂O is diethyl ether.)

Textbook Question

Under which of the following reaction conditions will (R)-1-chloro-1-phenylethane form the most (R)-1-phenyl-1-ethanol: in water or in 1.0 M HO⁻?

Textbook Question

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

e. 1-bromo-2-butene + CH₃O⁻

f. 1-bromo-2-butene + CH₃OH

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Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.(c)

Key Concepts

Cyclohexane Structure

Nucleophilic Substitution Reactions

Functional Group Transformation

Watch next

Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.
(c)