Help! Aromatic Carbonyl Compounds…?
Question by M-Z: help! aromatic carbonyl compounds…?
(A) is a mono-substituted aromatic carbonyl compound, optically inactive, of formula C9H10O, which
has been evaluated as a drug candidate for the treatment of type 2 diabetes.
thank you so much.
– (A) gives a positive silver mirror test with Tollens’ reagent.
– (A) is oxidised to (B) by Fehling’s solution.
– (B) reacts with methanol in the presence of H+ catalyst to give (C) of formula C10H12O2 and water.
– (A) reacts with hydrazine (NH2-NH2) to give (D) of formula C9H12N2 and water.
Identify (A), (B), (C) and (D) giving structures and a brief explanation on how you arrived at those
structures.
Best answer:
Answer by Zor Prime
Lancenigo di Villorba (TV), Italy
(A) is an AROMATIC COMPOUND HAVING EMPIRICAL FORMULA C8H10O. I may suppose a lot of possible isomers….
IS (A) AN ALCOHOL? AN ETHER? AN CARBONYLIC COMPOUND?
Really, there is a set of experimental overcomes which leads me to determinate molecular structure of (A).
CLUE N.1)
IT RESULTS A CARBONYLIC COMPOUND, then I HAVE TO EXCLUDE “Cyclic Acetals” AND “Benzopyran Alcohols” ; “Ethers” are yet excluded by empirical formula itself.
CLUE N.2)
IT RESULTS OPTICALLY INACTIVE, then it hasn’t Chiral Centers and I CAN’T CONSIDER “Alpha-Phenyl-Propanal”.
CLUE N.3)
IT GET POSITIVE REMARK TO Tollens’ Test, the I CAN’T CONSIDER KETONEs LIKE “Phenyl-propanone”.
CLUE N.4)
IT GET POSITIVE REMARK TO Fehling’s Test, the I HAVE TO CONSIDER AROMATIC ALDEHYDEs LIKE “Beta-Phenyl-Propanal”.
Now, “BETA-PHENYL-PROPANAL” is (A) and it has to turn into (B) LIKE “BETA-PHENYL-PROPANOIC ACID”.
…H-C=C-H
…../……\
H-C…….C-CH2-CH2-C=O…(A)
….\……//……………..|
..H-C–C-H……………H
…H-C=C-H
…../……\
H-C…….C-CH2-CH2-C=O…(B)
….\……//……………..|
..H-C–C-H……………OH
CLUE N.5)
(B) TAKES PART TO Esterification (STRONG ACIDIC MEDIUM) WHERE IT MEET Methanol (e.g. CH3OH) AND IT FORMS (C) AS “METHYL BETA-PHENYL-PROPANOATE”.
…H-C=C-H
…../……\
H-C…….C-CH2-CH2-C=O…(C)
….\……//……………..|
..H-C–C-H……………OCH3
CLUE N.5)
(A) TAKES PART TO Acylic Addiction (MILD ACIDIC MEDIUM) WHERE IT MEET Hydrazine (e.g. N2H4) AND IT FORMS (D) AS “BETA-PHENYL-PROPANALDHYDRAZONE”.
…H-C=C-H
…../……\
H-C…….C-CH2-CH2-C=N-NH2…(D)
….\……//……………..|
..H-C–C-H……………H
I hope this helps you.
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