Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.
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Verified step by step guidance

1. 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.
2. 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.
3. 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).
4. Step 4: Ensure the reaction conditions are optimized for SN2 substitution, as steric hindrance in cyclohexane is minimal, allowing for efficient substitution.
5. 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.

Key Concepts

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.