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Alkene Reactions

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

 A. 2-methyl-2-pentene (CH3)2C=CHCH2CH3

B. 2-ethyl-1-butene (CH3CH2)2C=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.

Desired Product Response Boxes
a. 3-pentanone CH3CH2COCH2CH3 Starting Material
Reagent Number
b. 2-methyl-2-pentanol CH3CH2CH2C(OH)(CH3)2 Starting Material
Reagent Number
c. 2-ethyl-1-butanol (C2H5)2CHCH2OH Starting Material
Reagent Number
d. 2-methylpentane CH3CH2CH2CH(CH3)2 Starting Material
Reagent Number
e. 2-methyl-2,3-pentanediol (CH3)2C(OH)CHOHCH2CH3 Starting Material
Reagent Number
f. 3-bromo-3-methylpentane CH3CH2CBr(CH3)CH2CH3 Starting Material
Reagent Number
g. 1-bromo-2-ethyl-2-butanol BrCH2C(CH2CH3)2OH Starting Material
Reagent Number
h. 2-methyl-3-pentanol CH3CH2CH(OH)CH(CH3)2 Starting Material
Reagent Number
Reagents

1. HBr

2. HOBr

3. ozone (O3)

4. diborane (B2H6)
followed by H2O2 in base

5. peracetic acid (CH3CO3H)

6. KMnO4 in H2O
(or OsO4)

7. KOH

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

9. H2 + Pt or Pd catalyst
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