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Alkene Reactions

Three isomeric alkene starting materials are available for your use. They are shown on the left below. Using one of these compounds, and selecting reagents from the list on the right, indicate how the products a) through o) might be prepared. Each question requires two responses. Under Alkene enter 1, 2 or 3. Under Reagents enter a letter A through H, corresponding to your selection.

Alkenes Reagents

1. (CH3)2CHCH=CH2
3-methyl-1-butene

2. (CH3)2C=CHCH3
2-methyl-2-butene

3. CH2=C(CH3)CH2CH3
2-methyl-1-butene
A.
HCl		 B.
Br2 		C.
Hg(OAc)2
in water		 D.
B2H6
(BH3) in ether
E.
H2O2
in aq NaOH		 F.
KMnO4
in water.		 G.
HOBr		 H.
NaBH4
Alkene Reagent(s) Product Answer Evaluation
reaction arrow a) CH2BrCBr(CH3)CH2CH3
    1,2-dibromo-2-methylbutane



reaction arrow b) (CH3)2CClCH2CH3
    2-chloro-2-methylbutane
reaction arrow c) (CH3)2C(OH)CH2CH3
    2-methyl-2-butanol
reaction arrow d) (CH3)2CHCH(OH)CH2Br
    1-bromo-3-methyl-2-butanol
reaction arrow e) (CH3)2CHCH(OH)CH3
    3-methyl-2-butanol
reaction arrow f) (CH3)2CHCHClCH3
    2-chloro-3-methylbutane
reaction arrow g) (CH3)2CHCH(OH)CH2OH
    3-methyl-1,2-butanediol
reaction arrow h) (CH3)2CHCHBrCH2Br
    1,2-dibromo-3-methylbutane
reaction arrow i) HOCH2C(OH)(CH3)CH2CH3
    2-methyl-1,2-butanediol
reaction arrow j) HOCH2CH(CH3)CH2CH3
    2-methyl-1-butanol
reaction arrow k) (CH3)2C(OH)CH(OH)CH3
    2-methyl-2,3-butanediol
reaction arrow l) (CH3)2C(OH)CHBrCH3
    3-bromo-2-methyl-2-butanol
reaction arrow m) (CH3)2CBrCHBrCH3
    2,3-dibromo-2-methylbutane
reaction arrow n) CH2BrC(OH)(CH3)CH2CH3
    1-bromo-2-methyl-2-butanol
reaction arrow o) (CH3)2CHCH2CH2OH
    3-methyl-1-butanol

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