Dimethyl Sulfoxide
Which of following will give 2-methyl-1-butene as the only alkene product on treatment w/ KOC(CH3)3 in…..?
dimethyl sulfoxide?
A. 2-methylbutane
B. 2-methyl-1-butanol
C. 2-bromo-2-methylbutane
D. 1-bromo-2-methylbutane
Help please
Thanks a lot!
The answer is ‘D’, 1-bromo-2-methylbutane. The reason is because potassium tert-butoxide (KOC-(CH3)3) is a strong enough base which can easily cause a beta-elimination reaction, the type of elimination that is occurring here. What happens is this…the proton attached to the C-2 carbon is abstracted by the base (potassium-tert-butoxide), which produces tert-butanol in the process. The electrons that used to bond the abstracted hydrogen then flow towards the C-1 carbon and make a double bond between the C-1 and C-2 carbons while kicking out a bromine ion (Br-) in the process. The resulting product is 2-methyl-1-butene. Incidently, this is called a beta-elimination reaction because it is initiated by a proton abstraction at the carbon atom that is ‘beta’ to (1 carbon away from) the leaving group.
Hope this helps!!!
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