Answer to Question #94140 in Organic Chemistry for Victoria

Question

Which of the compound undergo dehydrochlorination readily A=2 chloro 2 methyl butane, B=2 chloro butane, C=chloropropane
What informs your answer

Answer 1

Let's take a closer look at each of the mentioned structures:

As we know, the more branched alkenes are more stable thermodynamically. So we can assume that the formation of the more stable alkene would be faster, than less stable one - due to lower overall energy of the molecule. So, 2-chloro-2-methylbutane will form 2-methylbutene-2 upon dehydrochlorination. 2-chlorobutane will form butene-2, and 1-chloropropane will form propene-1 under the same circumstances (figure below).

In that case, 2-methylbutene-2 will be the most branched, thus most stable, alkene. So its formation would be fastest among all mentioned compounds. 2-chlorobutane will form less branched butene-2, so its formation would be slower, than in a case with a 2-chloro-2-methylbutane. 1-chloropropane will be the least active in the dehydrochlorination reaction among the three mentioned compounds.