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Chapter 9: Q113P (page 391)

Which of the following hexachlorocyclohexanes is the least reactive in an E2 reaction?

Short Answer

Expert verified

The 3rd structure will be least reactive to E2 reaction as it has no C-Cl and C-Br groups in trans periplanar orientation.

Step by step solution

01

Definition of E2 reaction

E2 reaction is an elimination reaction where H abstraction and C-Br bond breaking happens simultaneously having a trans periplanar arrangement between the C-H and C-Br bond.

02

Reason of least reactivity

E2 reaction preferably happens in the trans periplanar arrangement or in syn periplanar of C-Br and C-H bonds for the stable 5 membered transition state. So, if the two bond are in syn-periplanar position, the reaction will not be as fast as it should be. To understand which compound is least reactive, we have to check their structure.

Though the 2nd structure has 3 Cl bonds in the axial position, The 3rd structure has no anti periplanar C-H and C-Br bond. So, the 3rd structure will be least reactive.

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Most popular questions from this chapter

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

a. ethoxide ion or tert-butoxide ion

b. -OCN or -SCN

c. Cl- or Br-

d. CH3S- or CH3O-

Why is a cumulated diene not formed in the reaction shown below?

Draw the stereoisomers that are formed from the following SN1 reactions:

a. 3-bromo-3-methylpentane and methanol

b. 3-chloro-3-methylhexane and methanol

Rank the following alkyl bromides from most reactive to least reactive in an SN2 reaction:

1-bromo-2-methylbutane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, and 1-bromopentane.

What products will be obtained from the E1 reaction of the alkyl halides in Problem 45?
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