28. Consider the solvolysis of the two isomeric chiral p-nitrobenzoates 10 and 11. H 10 180 OLA M 11 -NO₂ O₂N- (a) Draw the structure of the free ion that would be formed by complete dissociation. What would be the stereochemistry of product formed from this ion? (b) The compounds labeled with 180 as indicated racemize during solvolysis; ¹80 equilibra- tion is also observed. For Isomer 10, keq = krac What does this result imply about the structure of the ion pair? (c) For Isomer 11, keq> krac What does this result imply about the structure of the ion pair? (d) Propose a reason for the difference of behavior of the two isomers.
28. Consider the solvolysis of the two isomeric chiral p-nitrobenzoates 10 and 11. H 10 180 OLA M 11 -NO₂ O₂N- (a) Draw the structure of the free ion that would be formed by complete dissociation. What would be the stereochemistry of product formed from this ion? (b) The compounds labeled with 180 as indicated racemize during solvolysis; ¹80 equilibra- tion is also observed. For Isomer 10, keq = krac What does this result imply about the structure of the ion pair? (c) For Isomer 11, keq> krac What does this result imply about the structure of the ion pair? (d) Propose a reason for the difference of behavior of the two isomers.
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Transcribed Image Text:28. Consider the solvolysis of the two isomeric chiral p-nitrobenzoates 10 and 11.
H
10
180
OLA
M
11
-NO₂ O₂N-
(a) Draw the structure of the free ion that would be formed by complete dissociation. What
would be the stereochemistry of product formed from this ion?
(b) The compounds labeled with 180 as indicated racemize during solvolysis; ¹80 equilibra-
tion is also observed. For Isomer 10, keq = krac What does this result imply about the
structure of the ion pair?
(c) For Isomer 11, keq> krac What does this result imply about the structure of the ion
pair?
(d) Propose a reason for the difference of behavior of the two isomers.
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