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3-Chlorocyclopropene, on treatment with AgBF4, gives a precipitate of AgCl and a stable solution of a product that shows a single 1HNMR absorption at 11.04 d. What is a likely structure for the product, and what is its relation to Hückel’s rule?

3-Chlorocyclopropene

Short Answer

Expert verified

The reaction of 3-chlorcylopropene with AgBF4

Step by step solution

01

Aromatic

Aromatic: A molecule must be cyclic planar, completely conjugated, must satisfy huckle’s ruleHuckle’s rule(4n+2)πelectrons, and contains a particular number of pi electrons.

02

3-chlorocyclopropene

The compound 3-chlorocyclopropene readily reacts with silver tetrafluoroborate(AgBF4) gives a stable salt (product)

The reaction of 3-chlorcylopropene with AgBF4

The cycloprep-2-en-1-ilium combines with BF4-and forms the stable salt. Here, Ag+ combines with Cl-and forms AgCl precipitate.

The formed product shows a single absorption in 1HNMR at 11.04 ppm because of its aromatic nature. The carbocation formed in the product is sp2 hybridized with a vacant p orbital, so it is planar and satisfies Huckel’s rule (here n=0). Thus, the cyclopropenyl cation that is formed as a product is aromatic. Its resonance structures are as shown:

Resonance structures

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