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Synthesis of cyclohexane -1,2 diol f...

Synthesis of cyclohexane -1,2 diol from cyclohexene may be accomplished in two ways :
I `MnO_(4)` dilute `OH, O^(@)C` dihydroxylation
II . Peracid epoxidation followed by NaOH opening of the epoxide ring .
Which of the following statement about the products from these reactions is correct ?

A

Methods I and II give same product

B

Method I gives resolvable racemic mixture while method II will give non- resolvable achiral product

C

Method I gives resolvable optically inactive compound while method II gives resolvable racemic mixture

D

Products obtained through method I and II will have diasteriomeric relationship

Text Solution

AI Generated Solution

The correct Answer is:
To synthesize cyclohexane-1,2-diol from cyclohexene, we can use two methods: ### Method I: Dihydroxylation using KMnO4 1. **Reagents**: Use cold and dilute potassium permanganate (KMnO4) in a basic medium. 2. **Reaction Mechanism**: - Cyclohexene reacts with KMnO4, leading to the formation of a cyclic intermediate. - This intermediate undergoes syn-dihydroxylation, where both hydroxyl (OH) groups are added to the same side of the double bond. 3. **Product Formation**: The product is a syn addition of hydroxyl groups, resulting in a compound that has a plane of symmetry, making it optically inactive. ### Method II: Epoxidation followed by Hydrolysis 1. **Reagents**: Use a peracid (like m-chloroperbenzoic acid) to form an epoxide from cyclohexene. 2. **Reaction Mechanism**: - Cyclohexene reacts with the peracid to form an epoxide. - The epoxide ring is then opened by sodium hydroxide (NaOH) in a nucleophilic attack, leading to the formation of two hydroxyl groups. - This process results in anti-dihydroxylation, where the hydroxyl groups are added to opposite sides of the double bond. 3. **Product Formation**: The product is an anti addition of hydroxyl groups, resulting in a compound that does not have a plane of symmetry, making it chiral. ### Comparison of Products - **Method I** yields a syn-diol which is optically inactive due to the presence of a plane of symmetry. - **Method II** yields an anti-diol which is chiral and can exist as a racemic mixture. ### Conclusion The correct statement regarding the products from these reactions is: - Method I gives a resolvable optically inactive compound, while Method II gives a resolvable racemic mixture. ### Final Answer The correct statement is: "Method 1 gives a resolvable optically inactive compound while method 2 gives a resolvable racemic mixture." ---

To synthesize cyclohexane-1,2-diol from cyclohexene, we can use two methods: ### Method I: Dihydroxylation using KMnO4 1. **Reagents**: Use cold and dilute potassium permanganate (KMnO4) in a basic medium. 2. **Reaction Mechanism**: - Cyclohexene reacts with KMnO4, leading to the formation of a cyclic intermediate. - This intermediate undergoes syn-dihydroxylation, where both hydroxyl (OH) groups are added to the same side of the double bond. 3. **Product Formation**: The product is a syn addition of hydroxyl groups, resulting in a compound that has a plane of symmetry, making it optically inactive. ...
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