### 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
--- | --- | --- | --- | --- | ---
|  |  | a) CH2BrCBr(CH3)CH2CH3 1,2-dibromo-2-methylbutane |
|  |  | b) (CH3)2CClCH2CH3 2-chloro-2-methylbutane
|  |  | c) (CH3)2C(OH)CH2CH3 2-methyl-2-butanol
|  |  | d) (CH3)2CHCH(OH)CH2Br 1-bromo-3-methyl-2-butanol
|  |  | e) (CH3)2CHCH(OH)CH3 3-methyl-2-butanol
|  |  | f) (CH3)2CHCHClCH3 2-chloro-3-methylbutane
|  |  | g) (CH3)2CHCH(OH)CH2OH 3-methyl-1,2-butanediol
|  |  | h) (CH3)2CHCHBrCH2Br 1,2-dibromo-3-methylbutane
|  |  | i) HOCH2C(OH)(CH3)CH2CH3 2-methyl-1,2-butanediol
|  |  | j) HOCH2CH(CH3)CH2CH3 2-methyl-1-butanol
|  |  | k) (CH3)2C(OH)CH(OH)CH3 2-methyl-2,3-butanediol
|  |  | l) (CH3)2C(OH)CHBrCH3 3-bromo-2-methyl-2-butanol
|  |  | m) (CH3)2CBrCHBrCH3 2,3-dibromo-2-methylbutane
|  |  | n) CH2BrC(OH)(CH3)CH2CH3 1-bromo-2-methyl-2-butanol
|  |  | o) (CH3)2CHCH2CH2OH 3-methyl-1-butanol

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