Alkene Reagent Selection

In each reaction box enter a letter designating the best reagent and conditions selected from the list on the right of the page.
Remember, the hydroboration and oxymercuration reactions take place in two independent steps; therefore, in these cases two reagents must be entered in the answer box in the correct order.

Reactant Reagent Product Answer
Evaluation
REAGENTS
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
(CH3)2CHCH=CH2
3-methyl-1-butene

(CH3)2CHCHClCH3
2-chloro-3-methylbutane



(CH3)2CHCHBrCH2Br
1,2-dibromo-3-methylbutane
(CH3)2CHCH2CH2OH
3-methyl-1-butanol
(CH3)2CHCH(OH)CH2Br
1-bromo-3-methyl-2-butanol
(CH3)2CHCH(OH)CH3
3-methyl-2-butanol
(CH3)2CHCH(OH)CH2OH
3-methyl-1,2-butanediol

Response Box

 
(CH3)2C=CHCH3
2-methyl-2-butene

(CH3)2CHCH(OH)CH3
3-methyl-2-butanol



(CH3)2C(OH)CH2CH3
2-methyl-2-butanol
(CH3)2CBrCHBrCH3
2,3-dibromo-2-methylbutane
(CH3)2CClCH2CH3
2-chloro-2-methylbutane
(CH3)2C(OH)CH(OH)CH3
2-methyl-2,3-butanediol
(CH3)2C(OH)CHBrCH3
3-bromo-2-methyl-2-butanol
CH2=C(CH3)CH2CH3
2-methyl-1-butene

CH2BrCBr(CH3)CH2CH3
1,2-dibromo-2-methylbutane

REAGENTS
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


(CH3)2CClCH2CH3
2-chloro-2-methylbutane
(CH3)2C(OH)CH2CH3
2-methyl-2-butanol
HOCH2CH(CH3)CH2CH3
2-methyl-1-butanol
CH2BrC(OH)(CH3)CH2CH3
1-bromo-2-methyl-2-butanol
HOCH2C(OH)(CH3)CH2CH3
2-methyl-1,2-butanediol

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