Compound 5 (shown below) displays intriguing reactivity features at distinct pHs. We will explore several examples. OH pH 13 OH ОН О LIOH 7 8 H20 ОН О ОН ОН pH 7 + CO2 HO ОН ОН ÓH Ö 10 (a) When 5 and 6 are treated with LIOH and the pH is further adjusted to highly basic (pH 13–14), products 7 and 8 are predominantly formed. Propose a reasonable mechanism for this reaction. OH OH LIOH рH 13 H H2O ÓH O ÓH Ö 7 Hints: a somewhat challenging pathway; start with Aldol chemistry and recall the extreme pH! You may be able to “take advantage" of intramolecular H transfer. (b) When 5 and 6 are treated with LIOH and the pH is further adjusted close to neutral (pH 6–8), products 9 and 10 (in addition to CO2) are predominantly formed. Propose a reasonable mechanism for this reaction. OH ОН ОН LIOH pH 7 H H20 но + CO2 О ОН ОН OH O 6 10
Compound 5 (shown below) displays intriguing reactivity features at distinct pHs. We will explore several examples. OH pH 13 OH ОН О LIOH 7 8 H20 ОН О ОН ОН pH 7 + CO2 HO ОН ОН ÓH Ö 10 (a) When 5 and 6 are treated with LIOH and the pH is further adjusted to highly basic (pH 13–14), products 7 and 8 are predominantly formed. Propose a reasonable mechanism for this reaction. OH OH LIOH рH 13 H H2O ÓH O ÓH Ö 7 Hints: a somewhat challenging pathway; start with Aldol chemistry and recall the extreme pH! You may be able to “take advantage" of intramolecular H transfer. (b) When 5 and 6 are treated with LIOH and the pH is further adjusted close to neutral (pH 6–8), products 9 and 10 (in addition to CO2) are predominantly formed. Propose a reasonable mechanism for this reaction. OH ОН ОН LIOH pH 7 H H20 но + CO2 О ОН ОН OH O 6 10
Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
Problem 37AP
Related questions
Question
Please provide mechanisms for these reactions
![Compound 5 (shown below) displays intriguing reactivity features at distinct pHs. We will
explore several examples.
OH
O.
рH 13
OH
ОН О
LIOH
7
8
H2O
ОН О
ОН ОН
5
6
pH 7
+ CO2
HO
ОН ОН
ОН О
10
(a) When 5 and 6 are treated with LIOH and the pH is further adjusted to highly basic
(pH 13–14), products 7 and 8 are predominantly formed. Propose a reasonable
mechanism for this reaction.
OH
OH
LIOH
pH 13
O.
H2O
Он О
ОН О
7
8
Hints: a somewhat challenging pathway; start with Aldol chemistry and recall the extreme
pH! You may be able to "take advantage" of intramolecular H transfer.
(b) When 5 and 6 are treated with LIOH and the pH is further adjusted close to neutral
(pH 6-8), products 9 and 10 (in addition to CO2) are predominantly formed. Propose
a reasonable mechanism for this reaction.
OH
ОН ОН
LIOH
pH 7
HO
+ CO2
H2O
ÓH Ö
ОН ОН
ОН О
5
10](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ff9f4d991-11a1-4c39-8723-6833123ab300%2F107d6179-7574-4374-98fd-9e64b3e522fd%2Fn216to5_processed.png&w=3840&q=75)
Transcribed Image Text:Compound 5 (shown below) displays intriguing reactivity features at distinct pHs. We will
explore several examples.
OH
O.
рH 13
OH
ОН О
LIOH
7
8
H2O
ОН О
ОН ОН
5
6
pH 7
+ CO2
HO
ОН ОН
ОН О
10
(a) When 5 and 6 are treated with LIOH and the pH is further adjusted to highly basic
(pH 13–14), products 7 and 8 are predominantly formed. Propose a reasonable
mechanism for this reaction.
OH
OH
LIOH
pH 13
O.
H2O
Он О
ОН О
7
8
Hints: a somewhat challenging pathway; start with Aldol chemistry and recall the extreme
pH! You may be able to "take advantage" of intramolecular H transfer.
(b) When 5 and 6 are treated with LIOH and the pH is further adjusted close to neutral
(pH 6-8), products 9 and 10 (in addition to CO2) are predominantly formed. Propose
a reasonable mechanism for this reaction.
OH
ОН ОН
LIOH
pH 7
HO
+ CO2
H2O
ÓH Ö
ОН ОН
ОН О
5
10
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