[AGF]

Hey everyone,
Here's the question.
"Suggest a reasonable synthetic strategy for the synthesis of 1-Bromo-2-Methylcyclohexane from Methylcyclohexane"

starting with methylcyclohexane I am going to do a SN2 reaction to make it 1-bromo-cyclohexane. Then i have to use a strong base to undergo an E2 reaction to create a double bond. I don't know which base to use that will set me up to create the 1-bromo-2-methylcyclohexane... then after I have the double bond formed, should i react the compound with HBr to create the 1-bromo-2-methylcyclohexane?

Thanks

[Fluorine]

1) "methylcyclohexane"  --S_N2--> X "1-bromo-cyclohexane"

What is your leaving group in the suggested S_N2 approach - methyl? That's not going to go through. Try setting it up for the next step a different way. The idea is correct but the approach is wrong.

2)      ?       --E2-->       ??     

Your logic is correct however you wrote "to create the 1-bromo-2-methylcyclohexane". Elimination in the second step will yield a new product not listed. Deciding the base will be easier when you fill in the blanks

3)      ??        ---> 1-bromo-2-methylcyclohexane

HBr alone will give Markovnikov or anti-Markovnikov? Which one will yield your product?