1. How to be, become, stay successful in this class (i.e. get a good grade!!) Attend every class (including lab lecture!) Preview/review and study lectures. Do Practice questions and problems on sample exams See your teacher when problems come up Study well for quizzes/exams, and start studying early For a Midterm grade see your lab instructor

2. Questions, Problems re. Unknown 1?

3. Today: Unknown 1 (conclusion) Unknown 2

4. Alcohol and Phenol Derivatives with 3,5-dinitrobenzoyl chloride urethanes →Take Home Miniquiz (2 pts.): Write a mechanism for the formation of the phenylurethane of 1-butanol Due by next lab lecture (late ones not accepted…) Preliminary tests Solubility Classification tests Derivatives Spectra Similarly: naphthyl urethanes

5. Alcohols IR: H-NMR: Exchange with D 2 O Preliminary tests Solubility Classification tests Derivatives Spectra OH in gas phase ….?? H-bonded!

6. Phenols H-NMR IR

7. Unknown 2 Carboxylic Acids Anhydrides Esters Amides Amines Nitro Functional groups of the above?

8. 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 Carboxylic Acids Anhydrides Esters Amides Amines Nitro Preliminary tests Solubility? Classification tests Derivatives Spectra

9. Preliminary test results? Mp., bp., odor, color… Preliminary tests? Solubility Classification tests Derivatives Spectra Carboxylic Acids Anhydrides Esters Amides Amines Nitro

10. Carboxylic Acids Good mp.s (consider recrystallization) Neutralization Equivalent (titration) experimental instructions on our webpage Solubility Classification tests Derivatives (not done) Spectra Derivatives (we do not do them in the lab): Convert carboxylic acid into acid chloride first, then into amides RCO 2 H+NaOH RCO 2 (–) Na (+) aq. + H 2 O 1. 2. + HCl

11. Esters Classification Test Deep-red to purple Preliminary tests? Solubility Classification tests Derivatives Spectra Compare with known ester! a hydroxamic acid

12. Derivatives for Esters Hydrolyze (experimental instructions on our webpage) … to its carboxylic acid component (mp.) …. and its alcohol component alcohol derivative Preliminary tests? Solubility Classification tests Derivatives Spectra

13. Amines Derivatives Picrates Benzamides: amine + benzoyl chloride NH 2 OH NO 2 2 O 2 N + Preliminary tests? Solubility Classification tests Derivatives Spectra

14. Carboxylic Acids IR: H-NMR: Preliminary tests? Solubility Classification tests Derivatives Spectra OH in gas phase (non-H-bonded)

15. Amines IR: H-NMR: Voodoo Lily

16. Amides H-NMR : Preliminary tests? Solubility Classification tests Derivatives Spectra IR?

17. Nitro Compounds Typical properties? Classification test: Always do with a known compound to compare! Derivatives: Reduce to amine and then prepare amine derivatives Preliminary tests? Solubility Classification tests Derivatives Spectra Iron (II) Hydroxide Test for Nitro Groups Nitro Compounds

18. IR (your take home miniquiz is due…) Inert Compounds: Alkanes Aromatic Hydrocarbons Alkyl halides Next time (11/4):