Alkene Reactions

Two isomeric alkene starting materials are available for your use. They are:

 A. 2-methyl-2-butene   (CH3)2C=CHCH3

B. 3-methyl-1-butene   (CH3)2CHCH=CH2

Using one or the other of these compounds, and selecting reagents from the list on the right, indicate how the following products might be prepared.
Each question (a. through h.) requires two responses. Under Starting Material enter A or B. Under Reagents enter a number corresponding to your selection.
Ignore the possibility of molecular rearrangement.

Desired ProductResponse Boxes
a.   2-chloro-3-methylbutane   (CH3)2CHCHClCH3Starting Material  
Reagent Number  
b.   2-bromo-2-methylbutane   (CH3)2CBrCH2CH3Starting Material  
Reagent Number  
c.   2-methylbutane   (CH3)2CHCH2CH3Starting Material  
Reagent Number  
d.   3-bromo-2-methyl 2-butanol   (CH3)2C(OH)CHBrCH3Starting Material  
Reagent Number  
e.   3-methyl-2-butanol   (CH3)2CHCH(OH)CH3Starting Material  
Reagent Number  
f.   3-methyl-1-chloro-2-butanol   (CH3)2CHCH(OH)CH2ClStarting Material  
Reagent Number  
g.   3-methyl-1-butanol   (CH3)2CHCH2CH2OHStarting Material  
Reagent Number  
h.   2-methyl-2-butanol   (CH3)2C(OH)CH2CH3Starting Material  
Reagent Number  
Reagents

1.   HBr (conc.)

2.   HOBr

3.   30% H2SO4 in water

4.   diborane (B2H6)
      followed by H2O2 in base

5.   HOCl  

6.   acetic acid (CH3CO2H)

7.   HCl in CHCl3  

8.   mercuric acetate [Hg(OAc)2]
      followed by NaBH4 in ethyl alcohol  

9.   H2 + Pt or Pd catalyst