Checking Ochem Reaction Validity: 1-Methyl-1-Cyclohexanol with HBr and EtO-/EtOH

[tandoorichicken]

I did this problem a little differently than my professor, so I need someone to check if it is valid.

Let's start with 1-methyl-1-cyclohexanol. If I react this with HBr, I should get 1-bromo-1-methylcyclohexane. And if I then react this with EtO-/EtOH, I should get 1-methyl-1-cyclohexene, right?

My professor wrote a reaction with sulfuric acid to give a carbocation that reacted with water to give the same product.

 

[GCT]

You are going to need to consider whether the carbocation site would transfer itself in this case, also, remember that the elimination mechanism takes place in trans.

 

[Blueshift5]

it is important to carefully consider the validity of any reaction, especially when it is done differently than what is typically taught. Let's break down the proposed reaction steps and evaluate their feasibility.

Firstly, the reaction between 1-methyl-1-cyclohexanol and HBr to form 1-bromo-1-methylcyclohexane is a well-known acid-catalyzed substitution reaction. This step is valid and can be supported by literature data.

Next, the proposed reaction between 1-bromo-1-methylcyclohexane and EtO-/EtOH to form 1-methyl-1-cyclohexene is a base-catalyzed elimination reaction. This step is also valid and has been reported in the literature.

However, the use of sulfuric acid to generate a carbocation intermediate, which then reacts with water to give the same product, is not a commonly used method in this type of reaction. In fact, it is more common to use a strong base such as potassium hydroxide or sodium hydroxide to promote the elimination reaction. Therefore, it would be helpful to know the rationale behind using sulfuric acid in this case.

In conclusion, the proposed reaction steps are valid and can lead to the formation of 1-methyl-1-cyclohexene. However, the use of sulfuric acid as a catalyst may require further explanation or justification. It would also be beneficial to compare the yields and reaction rates of the two methods to determine the most efficient approach.