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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 Product Response Boxes
a. 2-chloro-3-methylbutane (CH3)2CHCHClCH3 Starting Material
Reagent Number
b. 2-bromo-2-methylbutane (CH3)2CBrCH2CH3 Starting Material
Reagent Number
c. 2-methylbutane (CH3)2CHCH2CH3 Starting Material
Reagent Number
d. 3-bromo-2-methyl 2-butanol (CH3)2C(OH)CHBrCH3 Starting Material
Reagent Number
e. 3-methyl-2-butanol (CH3)2CHCH(OH)CH3 Starting Material
Reagent Number
f. 3-methyl-1-chloro-2-butanol (CH3)2CHCH(OH)CH2Cl Starting Material
Reagent Number
g. 3-methyl-1-butanol (CH3)2CHCH2CH2OH Starting Material
Reagent Number
h. 2-methyl-2-butanol (CH3)2C(OH)CH2CH3 Starting 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


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