Molecular formula of organic compound

[TT0]

Homework Statement

Homework Equations

The Attempt at a Solution

Firstly I tried to find the empirical formula:

C : H : O
65.2 : 8.75 : 26.05 (mass)
5.43 : 8.75 : 1.628 (mol)
3.34 : 5.37 : 1
10 : 16 : 3
C₁₀H₁₆O₃

This gives a molecular mass of 184.

Now with the structure: It has to contain a carboxylic group. I used trial and error and got the structure 1-hydroxyl dec-2-eneoic acid. Not sure if my naming is correct but the general idea is that there is a alcohol on one end, carboxylic acid on the other end, and a double bond in between. This means the mol of NaOH used = mol of compound Q. NaOH = 0.000237 mol. Molar mass = 0.0437 gram/0.000237 mol = 184.38 g/mol.

Does this seems correct?

Cheers!

 

[Ygggdrasil]

What is the degree of unsaturation of the molecule? How many degrees of unsaturation does your proposed compound have? (Note that the problem does not require you to give a structural formula as many different structural formulas would be consistent with the observations given).

 

[TT0]

According to the alkane molecular formula there are 3 degrees of unsaturation since there needs to be 22 hydrogens for a 10 carbon compound to be saturated. However, for the molecule I proposed, I only had 2 degrees of unsaturation so I need to add another double bond. I miscounted before :( Thanks!