Answer to Question #93954 in Organic Chemistry for Elkan

Question

A= 2 chloro 2 methyl butane
B= 2 chloro butane
C= chloro propane.
i, which of the following compounds will undergo dehydrochlorination.
ii, what informs your answer.

Answer 1

I) Each of the mentioned compounds will undergo dehydrochlorination under suitable conditions. Usually, it is the treatment with a potassium hydroxide solution in alcohol. Although, the activity of mentioned compounds towards dehydrochlorination reactions would differ and will decrease in a row A>B>C.

II) This pattern could be explained by the fact, that the formation of the more stable product is always favorable. In case A the chlorine atom is attached to the tertiary carbon atom, so there will be three methyl groups, which stabilize final alkene (two methyl groups attached directly to the same carbon atom and one attached to the adjacent carbon atom). In case B there will be only two methyl groups near future double bond, so the formation of the alkene will be slower. In case C only one methyl group stabilizes final alkene, so the formation of such structure will be slowest.