How to be, become, stay successful in this class (i.e. get a good grade!!)

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. Preliminary tests • Solubility • Classification tests • Derivatives • Spectra Alcohol and Phenol Derivatives • with 3,5-dinitrobenzoyl chloride • urethanes Similarly: naphthyl 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…)

5. Preliminary tests • Solubility • Classification tests • Derivatives • Spectra Alcohols IR: H-bonded! OH in gas phase ….?? H-NMR: Exchange with D2O

6. Phenols IR H-NMR

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

8. Preliminary tests • Solubility? • Classification tests • Derivatives • Spectra Carboxylic Acids Anhydrides Esters Amides Amines Nitro Solubility Tests What type of information do you get if your unknown 1. is soluble in water? 2. is soluble in NaOH and in NaHCO3? 3. is soluble in NaOH only, not in NaHCO3? 4. is soluble in dilute HCl solution? 5. is soluble only in conc H2SO4? 6. is not soluble in any of the above solvents?

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

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

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

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

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

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

15. Amines IR: Voodoo Lily H-NMR:

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

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

18. Next time (11/4): • Inert Compounds: • AlkanesAromatic HydrocarbonsAlkyl halides • IR • (your take home miniquiz is due…)