Please help with chemistry 3 question!?

Question

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene as the only alkene product?

a.) 2-chloropentane
b.) 1-chloro-2-methylbutane
c.) 1-chloropentane
d.) 3-chloropentane
e.) 1-chloro-3-methylbutane

Please Help!

Answer 1

Best Answer - Chosen by Asker

You are probably overthinking this question. The answer is 3-chloropentane. The Cl or X is thus on the 3 C and the neighboring C's (2,4) both contain the hydrogen that is necesarry for dehydrohalogenation (secondary Hydrogens). Since they are both equally stable either product is equally likely. Both products just happen to be named pent-2-ene because you start with first C with the double bond and they meet in the middle at C #3.

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Thanks!