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. Answer Evaluati on REAGENTS A. HCl B. Br2 C. Hg(OAc )2 in water D. B2H6 (BH3) in ether H. NaB H4

Reactant

Reagent

Product

(CH3)2CHCHClCH3 2-chloro-3-methylbutane (CH3)2CHCHBrCH2Br 1,2-dibromo-3methylbutane (CH3)2CHCH2CH2OH 3-methyl-1-butanol (CH3)2CHCH(OH)CH2 Br 1-bromo-3-methyl-2butanol (CH3)2CHCH(OH)CH3 3-methyl-2-butanol (CH3)2CHCH(OH)CH2 OH 3-methyl-1,2-butanediol E. H2O2 in aq NaO H F. KMnO
4

in water.

G. HOBr

(CH3)2CHCH=C H2 3-methyl-1-butene

(CH3)2CHCH(OH)CH3 3-methyl-2-butanol (CH3)2C(OH)CH2CH3 2-methyl-2-butanol (CH3)2C=CHCH3 2-methyl-2-butene (CH3)2CBrCHBrCH3 2,3-dibromo-2methylbutane (CH3)2CClCH2CH3 2-chloro-2-methylbutane

Response Box

(CH3)2C(OH)CH(OH)C H3 2-methyl-2,3-butanediol (CH3)2C(OH)CHBrCH3 3-bromo-2-methyl-2butanol

CH2BrCBr(CH3)CH2C H3 1,2-dibromo-2methylbutane (CH3)2CClCH2CH3 2-chloro-2-methylbutane (CH3)2C(OH)CH2CH3 2-methyl-2-butanol HOCH2CH(CH3)CH2C H3 2-methyl-1-butanol CH2BrC(OH)(CH3)CH2 CH3 1-bromo-2-methyl-2butanol HOCH2C(OH)(CH3)C H2CH3 2-methyl-1,2-butanediol REAGENTS A. HCl B. Br2 C. Hg(OAc )2 in water D. B2H6 (BH3) in ether H. NaB H4

CH2=C(CH3)CH2 CH3 2-methyl-1-butene

E. H2O2 in aq NaO H

F. KMnO
4

in water.

G. HOBr

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

Reactions of 3-methyl-1-butene: A, B, DE, G, CH, F. ---------------------------------Reactions of 2-methyl-2-butene: DE, CH, B, A, F, G. ----------------------------------

Reactions of 2-methyl-1-butene: B, A, CH, DE, G, F.