1. Clickers! We will work out a synthetic route to achieve the following overall transformation in four steps.

2. Clickers! A:1) B 2 H 6, THF 2) NaOH, H 2 O 2 aq. B:1) O 3, CH 2 Cl 2 2) Zn/HOAc C:mCPBA, CH 2 Cl 2 D:KMnO 4, H 3 O + E:Hg(OAc) 2, H 2 SO 4 (aq.)

3. Clickers! KMnO 4, H 3 O +

4. Clickers! KMnO 4, H 3 O +

5. Clickers! KMnO 4, H 3 O + A:pTsOH, toluene,  B:CrO 3, H 2 SO 4 (aq.) C:mCPBA, CH 2 Cl 2 D:Sn, HOAc

6. Clickers! KMnO 4, H 3 O + pTsOH, toluene, 

7. Clickers – Spectroscopy. Data on an unknown organic compound whose formula is C 6 H 8 O 2 will be presented. The questions will follow.

8. IR Spectrum

9. Clicker question: The degree of unsaturation in this compound is: A:1 B:2 C:3 D:4

10. Clicker question: The degree of unsaturation in this compound is: A:1 B:2 C:3 D:4

11. Clicker question: From the IR spectrum, what functional group is likely to be present? A:Ester B:Ketone C:Carboxylic acid D:Nitrile

12. Clicker question: From the IR spectrum, what functional group is likely to be present? A:Ester B:Ketone C:Carboxylic acid D:Nitrile

13. NMR Spectra.

14. Clicker question: We know the compound contains a COOH group, and has 3 degrees of unsaturation. Based on this and the NMR spectra, what other functionality is present? A:Aromatic ring B:Alkyne C:Two Alkenes

15. Clicker question: We know the compound contains a COOH group, and has 3 degrees of unsaturation. Based on this and the NMR spectra, what other functionality is present? A:Aromatic ring B:Alkyne C:Two Alkenes

16. Clicker question: What is the structure of the unknown compound?

17. Clicker question: What is the structure of the unknown compound?