Organic Chemistry - Stereochemistry Problem

[skyisblue]

What is the stereochemistry of the product that results from addition of Br2 to 1-methylcyclohexene? Is the product optically active? Explain.

I have the solution to this problem, but I was just wondering if someone can explain it to me in layman's terms.......I'm having a hard time getting this down.....

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[CyborgNinjaX]

What is the stereochemistry of the product that results from addition of Br2 to 1-methylcyclohexene? Is the product optically active? Explain.

I have the solution to this problem, but I was just wondering if someone can explain it to me in layman's terms.......I'm having a hard time getting this down.....

This is a Markovnikov product because A) anti-markovnikov product would involve hydroboration (BH3). B) the double bond.

The product is going to be 1-bromo-1-methyl-cyclohexane and hydrobromic acid. My guess is going to be that it is not going to be active.

 

[slashnroses19]

the carbon 1 that is connected to the methyl group is achiral so it will not be optically active. its connected to two CH2s, a Br, and a CH3. what does your solution say?

 

[REH]

I think it might be 1,2-dibromo-1-methycyclohexane. There's a bromonium ion intermediate and the incoming bromide ion would attack anti to that. If that is the case, I believe it would generate a chiral carbon.

 

[skyisblue]

It's a 50:50 racemic mixture of R,R and S,S dibromides with each Br on opposite side. Yeah, these problems are tricky.