Experimental Details:
-When treated with base [hydroxide ion] and after appropriate workup, Compound F was converted into Compound G, which is the one and only product of this reaction.
-Compound F, when subjected to an elemental analysis experiment, gave the following results: C - 71.10% and H - 5.25%.
- Compound G, when subjected to an elemental analysis experiment, gave the following results: C –66.65% and H –5.60%
Questions:
-Based upon the experimental observations, determine the structure of Compound F.
- If you cannot unambiguously determine the structure of Compound F, explain why.
-Based upon the experimental observations, determine the structure of Compound G.
- If you cannot unambiguously determine the structure of Compound G, explain why.
-In what [mechanistic] way is the conversion of Compound F to Compound G similar
to the Cannizzaro reaction?
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My attempt:
Compound F:
C 71 H 5.25 O=100-71-5.25=23.5
0.71 g C/12.011 g C=0.0591 mol C
0.0525 g H/1.007 g H=0.0521 mol H
0.235 g O/15.99 g O=0.01469mol O
Compound F
C16H14O4
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Compound G
C=66.65 H=5.6 O=100-66.65-5.6=27.75
66.65 g C/12.011 g C=5.549 mol C
5.6 g H/1.007 g H=5.561 mol H
27.75 g O/15.99 g O=1.735mol O
Compound G
C16H16O5
net addition of H2O?
Perhaps this is the carboxylic acid product of the Cannizzaro Reaction.
In order for only the carboxylic acid product to form, it is a crossed Cannizzaro Reaction.
If the reaction occurs at an aldehyde of the starting chemical, how can the other oxygens be arranged so they are not affected? All ethers,esters,etc?
Thankyou