[rtkt01]

 Question: starting with 2-methylpropane outline a synthesis of each of following.

 1. t-butyl alcohol
                          Br2/light                                                KOH/alcohol                          H2O/H+
 2-methylpropane ---------> 2-bromo-2-methylpropane + HBr -----------> 2-methylpropene ------->

t-butylalcohol

2. 2,2,3,3,-tetramethylbutane
              
                      
                        Br2/light                                              2Li / diethylether          CH3              
 2-methylpropane ------------> 2-bromo-2-methylpropane -------------->      CH3-C -Li + LiBr
                                                                                                                  CH3
        CH3
  CH3-C -Li + LiBr              
        CH3

(2-methylpropane )2 CuLi + 2-bromo-2-methylpropane

                                                      CH3
---> 2,2,3,3,-tetramethylbutane + CH3-C -Cu + LiBr              
                                                      CH3
                                                                                                      
3. isobutyl methyl ether


                        Br2/light                                            
 2-methylpropane ------------> 2-bromo-2-methylpropane  + HBr

2-bromo-2-methylpropane +    CH3-O - Na +    --------->  isobutyl methyl ether +    Na + Br -


 Did I make any mistake?  

[nj_bartel]

I'm having a hard time understanding what's going on due to formatting, but in the last one, you tried to SN2 on a tertiary substrate.

[rtkt01]

I'm having a hard time understanding what's going on due to formatting, but in the last one, you tried to SN2 on a tertiary substrate.

Thank you for input.  What if I get isobutyl bromide from 2-methylpropane, and then use isobutyl bromide + CH3-O-Na+ -> isobutyl methyl ether ?

In the second one, I used Corey-Posner, Whitesides-House synthesis to get 2,2,3,3-tetramethylbutane from 2-methylpropane, but I'm not sure if I can use tertiary alkyl halide in R2CuLi + R'X part.

                                                                              Br2/light
Can I just use wurtz reaction like this ?      2-methylpropane ---->   2-bromo-2-methylpropane

                                      2Na/boil
2 2-bromo-2-methylpropane  -----> 2,2,3,3-tetramethylbutane + 2NaBr