Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(h)

Verified step by step guidance

1. Step 1: Begin with the starting material, 1,2-dimethylcyclohexene. The target compound has an alcohol (-OH) group attached to the carbon adjacent to the double bond. This suggests a hydration reaction.
2. Step 2: Use an acid-catalyzed hydration reaction to add water across the double bond. Employ a dilute acid such as H2SO4 in the presence of water. This reaction follows Markovnikov's rule, where the -OH group will attach to the more substituted carbon.
3. Step 3: Recognize that the product will be a racemic mixture if the reaction generates a chiral center. The stereochemistry of the product is not specified, so assume both enantiomers are formed.
4. Step 4: Verify the structure of the product. The -OH group should be attached to the carbon that is part of the original double bond and is more substituted, while the other carbon from the double bond will gain a hydrogen atom.
5. Step 5: Confirm that the resulting compound matches the target structure shown in the image, with the -OH group and a methyl group on the same carbon adjacent to the cyclohexane ring.

Key Concepts

Electrophilic Addition Reactions

Electrophilic addition reactions are fundamental in organic chemistry, particularly for alkenes like 1,2-dimethylcyclohexene. In these reactions, an electrophile reacts with the double bond of the alkene, leading to the formation of a more stable carbocation intermediate. This process is crucial for synthesizing alcohols, halides, and other functional groups from alkenes.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of synthesizing chiral compounds, understanding stereochemistry is essential, as it determines the configuration of the product. For example, when synthesizing 1,2-dimethylcyclohexanol, the stereochemical outcome can lead to different enantiomers, impacting the properties and reactivity of the compound.

Functional Group Interconversion

Functional group interconversion refers to the transformation of one functional group into another within a molecule. This concept is vital for organic synthesis, as it allows chemists to modify compounds to achieve desired properties. In the synthesis of compounds from 1,2-dimethylcyclohexene, converting the alkene to an alcohol (as seen in 1,2-dimethylcyclohexanol) exemplifies this principle, showcasing how different functional groups can be strategically introduced.