Question

For this discussion, you are asked once again to select organic compound from your text book or one that you found on the list of ingredients from a product in your home or select your favorite organic compound. No ionic compounds! The compound of your choice must be an organic compound. Please make sure you are able to answer the following questions regarding the compound of your choice. You may have difficulty answering the questions below if your compound of choice is complex.

In this case, the simpler the better. In order to earn full credit, you must clearly label all protons and carbon atoms in your structure.

I am choosing Aceteminophen

What is the name and structure of your compound? Please be sure to include the structure of your compound and not just the molecular formula.

What is the major function group in your compound (Hint: Look at the ending of the name of your compound for a hint).

List all of the other functional groups present in your compound.

What is the HDI (Hydrogen Deficiency Index) for your compound?

How many sets of non-equivalent protons are present in your compound?

Please label all protons in your structure and indicate what would be the multiplicity of each set of non-equivalent protons in your compound (singlet, doublet, etc.)?

How many peaks would you predict would appear in the Carbon-13 NMR spectrum?

Please label all carbons in your structure.

Which carbon atom in your compound would you predict would be the farthest downfield in your C-13 Spectrum?

Pick at least two functional groups present in your compound and describe where they would appear in the IR spectrum of this compound.

Please be sure to include the actual absorption frequencies in your discussion posting.

What would be the m/z value for the molecular ion peak of your compound? Remember m/z values are whole numbers.

Answer 1

Acetaminophen or Paracetamol:

1.Name: N-acetyl paraaminophenol.

A functional group is a specific group of atoms within a molecule that gives rise to the characteristic chemical reactions of the molecule.

The structure of acetaminophen is

OH NH-C CH

2.The functional groups in acetaminophen are hydroxyl, aromatic ring, and amide

The group at the top of the molecule is a hydroxyl group. It is tempting to call it an alcohol group.But an –OH group attached to a benzene ring has special properties. It is more commonly called a phenolic OH(major functional group).

The six-membered ring is an aromatic ring.

The group at the bottom of the molecule is a monosubstituted or secondary amide.

3.Formula of acetaminophen C8H9NO2

So HDI according to formula

= (8+1)-[(9-1)/2]

= 9 - 4

=5

4.Five set of nonequivalent protons will be there.

i.one Phenolic OH proton (singlet)

ii.Two aromatic proton ortho to phenolic OH( doublet)

ii.Two aromatic proton ortho to Amide group (doublet)

iv. One amide proton (singlet)

v. Three methyl proton( singlet)

5. Six peaks will appear in the Carbon-13 NMR spectrum.

i. One aromatic Carbon attached to OH

ii. Two aromatic carbon ortho to OH.

iii.Two aromatic carbon ortho to Amide.

iv. Aromatic carbon attached to amide.

v. Carbonyl carbon of amide.

vi. Methyl Carbon.