### 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.