10:21PM Sun Jul 28 = Q AA pKa = 39 Problem 15.12 Rank the following compounds in order of increasing acidity. Tropylium Cation A B с " ຈຸ ດ 68% Page 701 The tropylium cation is a planar carbocation with three double bonds and a positive charge contained in a seven-membered ring. This carbocation is completely conjugated, because the positively charged carbon is sp² hybridized and has a vacant p orbital that overlaps with the six p orbitals from the carbons of the three double bonds. Because the tropylium cation has three л bonds and no other nonbonded electron pairs, it contains six л electrons, thereby satisfying Hückel's rule. §

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10:21PM Sun Jul 28
=
Q AA
pKa = 39
Problem 15.12
Rank the following compounds in order of increasing acidity.
Tropylium Cation
A
B
с
"
ຈຸ ດ 68%
Page 701
The tropylium cation is a planar carbocation with three double bonds and a positive charge contained in a seven-membered ring. This
carbocation is completely conjugated, because the positively charged carbon is sp² hybridized and has a vacant p orbital that overlaps with
the six p orbitals from the carbons of the three double bonds. Because the tropylium cation has three л bonds and no other nonbonded electron
pairs, it contains six л electrons, thereby satisfying Hückel's rule.
§
Transcribed Image Text:10:21PM Sun Jul 28 = Q AA pKa = 39 Problem 15.12 Rank the following compounds in order of increasing acidity. Tropylium Cation A B с " ຈຸ ດ 68% Page 701 The tropylium cation is a planar carbocation with three double bonds and a positive charge contained in a seven-membered ring. This carbocation is completely conjugated, because the positively charged carbon is sp² hybridized and has a vacant p orbital that overlaps with the six p orbitals from the carbons of the three double bonds. Because the tropylium cation has three л bonds and no other nonbonded electron pairs, it contains six л electrons, thereby satisfying Hückel's rule. §
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