1. Midterm Key is in ERES file Class Average: 75.5 High: 100 Low: 27 Today: “Unknowns”: - Brief Review of Preliminary tests and Solubilities - Aldehydes and Ketones - Alcohols and Phenols (Unknown #1) Next time: Carboxylic acids Esters Amines (Unknown #2) Family Science Night Volunteers: Please see me after class

2. Mp. (range!) for solids Bp., refractive index for liquids Ignition test Test for unsaturation Beilstein test for halogen (p.626) Preliminary Tests

3. What type of information do you get if your unknown 1. is soluble in water? 2. is soluble in NaOH and in NaHCO 3 ? 3. is soluble in NaOH only, not in NaHCO 3 ? 4. is soluble in dilute HCl solution? 5. is soluble only in conc H 2 SO 4 ? 6. is not soluble in any of the above solvents? Solubility Tests (pp. 626 – 627)

4. Aldehydes and Ketones functional group? Typical properties? Mp.? Bp.? Solubility? Preliminary tests Solubility Classification tests Derivatives Spectra

5. 2,4-dinitrophenylhydrazone Classification Tests for Aldehydes and Ketones also a good derivative! 1.What are desirable properties of a derivative? 2.What is the purpose of preparing a derivative? Preliminary tests Solubility Classification tests Derivatives Spectra

6. Tollens Test: Jones (chromic acid): check reagent! Test is also positive for …..? Schiff reagent: check reagent! Always do with a known compound to compare! Aldehydes and Ketones To distinguish between aldehydes and ketones: Preliminary tests Solubility Classification tests Derivatives Spectra

7. Aldehydes and Ketones Derivatives Imines: 2,4-dinitrophenylhydrazone oxime semicarbazone Preliminary tests Solubility Classification tests Derivatives Spectra

8. What characteristics would you look for –in the IR spectrum of an aldehyde –In the HNMR of an aldehyde –In the CMR of an aldehyde? Preliminary tests Solubility Classification tests Derivatives Spectra Question….

9. Aldehydes and Ketones IR: H-NMR:

10. Alcohols and Phenols Solubility distinction? Solubility: Alcohols: “neutral”; Phenols: very weak acids, pKa around 10, except nitrophenols! Classification tests (many also positive with amines…): Jones Lucas test for 3 o alcohols, 2 o alcohols (slow): Phenols only: Complexation with Fe 3+ Preliminary tests Solubility Classification tests Derivatives Spectra

11. Anthocyanin Colors

12. Alcohol and Phenol Derivatives with 3,5-dinitrobenzoyl chloride urethanes Similarly: Naphthyl urethanes Phenols only: Bromoderivatives Preliminary tests Solubility Classification tests Derivatives Spectra

13. Alcohols IR: H-NMR: Exchange with D 2 O Preliminary tests Solubility Classification tests Derivatives Spectra

14. Phenols H-NMR IR

15. Next time: Carboxylic Acids and Esters Amines Review this class!