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 ProductResponse Boxes
a.   3-pentanone   CH3CH2COCH2CH3Starting Material  
Reagent Number  
b.   2-methyl-2-pentanol   CH3CH2CH2C(OH)(CH3)2Starting Material  
Reagent Number  
c.   2-ethyl-1-butanol   (C2H5)2CHCH2OHStarting Material  
Reagent Number  
d.   2-methylpentane   CH3CH2CH2CH(CH3)2Starting Material  
Reagent Number  
e.   2-methyl-2,3-pentanediol   (CH3)2C(OH)CHOHCH2CH3Starting Material  
Reagent Number  
f.   3-bromo-3-methylpentane   CH3CH2CBr(CH3)CH2CH3Starting Material  
Reagent Number  
g.   1-bromo-2-ethyl-2-butanol   BrCH2C(CH2CH3)2OHStarting Material  
Reagent Number  
h.   2-methyl-3-pentanol   CH3CH2CH(OH)CH(CH3)2Starting 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

This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.