Exercise 29.30 12 of 17> The reaction of an unknown with ethanol in the presence

Question

Exercise 29.30 12 of 17> The reaction of an unknown with ethanol in the presence of a small amount of H2SO leads to a compound that smells distinctly like rum. The protondecoupled 1C NMR spectrum of the product is as shown in the figure(slent). (Figure 1 Part A What is the structure of the unknown ? Spell out the full name of the compound. Submit Request Answer Part B What other structure(s) would be consistent with this 13C NMR spectrum? Enter your answers separated by a comma. Submit Figure 1 of 1> Provide Feedback Next>

Explanation / Answer

There are three peaks in C13 NMR.....

we know

unknown + C2 H5OH  ---------H2SO4---------------> product smell like rum

here in  C2 H5OH we have two different carbon atoms that can be detected in C13 NMR so it is clearly implies our unknown product have only one carbon atom.The given reaction is esterification reaction hence we need our product as carboxalic acid. and the only one carboxylic acid which contains one carbon atom is formic acid hence compound unknown is formic acid . HCOOH. the product formed in the reaction is Ethyl Formate (CH3CH2-O-CO-H)

A. Formic acid (HCOOH)

B. According to the C13 NMR data given three structures of the product can be possible,

CH3 -CO-CH2-OH ( 1- Hydroxy prop-2-one)

CH3-O-CO-CH3 (dimethylester)

CH3CH2-O-CO-H (ethyl formate)

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