a) b) Predicting Acidity Rank the following compounds in order of increasing acidity: 1 1 1 OH LOH Rel. Intensity 100 80 60 40 20 2 0.0+ OH 0.0 OH H₂ 0: Alcohols and Ethers Interpreting a Mass Spectrum give a peak at m/z = 45? 20 3 3 Example: Propose a structure for the following alcohol using the mass spectrum below (NOTE: there is a very small peak at m/z = 88) unknown MASS SPECTRUM 40 OH OH Ö-H 3 4 60 Hints: This is an alcohol, it has a mass of 88 so first determine the formula, then draw the possible structures. Now, which structure will fragment to OH OH 80 100

Which C-H bonds are responsible for the following peaks in the 1H NMR of this molecule? B= C=|| CTH1602 B PPM 10

1. What do you suppose is the molecular weight of the molecule that gives the mass spectrum below? 27 Hai 55 26 45 30 40 50 Rel Abund 100r 80- 60- 40- 20- 0- m/z0 10 Rel Abund = Relative Abundance Formula 1: 20 Formula 2: Formula 3: m/z = mass divided by charge 3. What is the base peak? 2. Provide three different molecular formulas (organic molecules, please) that are possible for a molecule with the molecular weight you have chosen. What are the degrees of unsaturation (SODAR) for each? Degrees of unsaturation: Degrees of unsaturation: Degrees of unsaturation: 60 4. Draw a possible molecule for each formula. based on Formula 1 5. Which structure do you think is correct? 72 70 based on Formula 2 80 What mass is lost from the molecular ion to get to the base peak? 90 100 based on Formula 3

4. Draw a possible molecule for each formula. based on Formula 1 5. Which structure do you think is correct? based on Formula 2 based on Formula 3

Determine the compound (name or structure) from the data. Explain features from each data.  Molecular formula: C6H5Br Use molecular formula to determine IHD IR: Identify the presence/absence of five key functional groups NMR: Analyze this last. Consider multiplicity and peak area to confirm compound. The 5 H peak area covers both peaks (at 7.1 and 7.5 ppm Structure?

The following MS spectrum is for a compound which contains one oxygen atom (as well as C and H, of course, but no other atoms). Propose a structure which is consistent with this MS; also identify the species responsible for each peak whose numerical m/z is given (remember resonance!). OP ALTAOSACO b d 100 80 60 40 20 0 0 20 31 40 60 m/z 77 80 91 % (M+1)/M = 7.93 100 107 108 120