chemistry

Chemistry 3010 Name: Dr. Dunlap

Problem Set #3

due in Dropbox June 14, 2020 (11:59PM)

(20 points)

1. (2 pts) Propose a structure consistent with the following data: C3H6O; IR peak at 1730 cm

-1; 1H-NMR δ 1.11 (t, 3H), 2.46 (m, 2H), 9.79 (t, 1H).

2. (6 pts) 1H-NMR, 13C-NMR and MS data are given for compound 1. In the IR, there is an absorbance at 1700cm-1. i) On the MS, label the molecular ion, base peak, and propose a FORMULA consistent with the MW, as well as the IR data. ii) In the 1H-NMR, draw a fragment responsible for signals at δ 7.2-8.1. iii) In the 13C-NMR, identify what is responsible for the signal at δ 200.4. iv) Propose a structure consistent with the data given.

3. (4 pts) A mass spectrum (left) and an IR spectrum (right) are given for compound X. What functional group is present, based on the IR? In the mass spectrum, label the molecular ion peak. Propose a formula that is consistent with the information given

4. (3 pts) What are the splitting patterns in the 1H-NMR (doublet, triplet, etc.) for each of the hydrogens labeled with arrows:

5. (5 pts) Answer the following questions based on this reaction:

i) Is this a substitution, elimination or addition reaction? ii) Explain how you could use IR to identify whether or not the product has formed in the reaction (give specific absorbances). iii) Explain how you could use 13C-NMR to identify whether or not the product has formed in the reaction (give specific absorbances).

O

OH K2Cr2O7 O