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.

Add your own answer in the comments!

Northampton County Council approves audit of prison treatment program for …
Council this week tasked the county controller with investigating recidivism rates, spending and accreditation at the county's Community Education Centers, which offer alcohol abuse treatment and parenting classes at the West Easton Treatment Center … Read more on The Express-Times