1. Questions of the day: What is the functional group of Carboxylic Acids Anhydrides Esters Amides Amines Nitro ???

2. Today: Unknown #2: Carboxylic Acids, Esters, Amides Amines (Cl, Br, nitro) MiniQuiz

3. Preliminary test results? Mp., bp. Which would you expect to have relatively high/relatively low mp.s / bp.s? Odor Which would you expect to have a bad smell/a pleasant smell (human perspective…) Color Which would you expect to have a color? Preliminary tests? Solubility Classification tests Derivatives Spectra Carboxylic Acids Anhydrides Esters Amides Amines Nitro

4. the ratio of the velocity of light in air to the velocity of light in a given medium. sin incident angle/sin refracted angle a constant at a given temperature. an important physical property of liquids (and gases and transparent solids!) Air has a refractive index of 1.000292 at 273 K/760 mm Hg for the yellow sodium D-line at 589.3 nm. Refractive Index:

5. 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

6. 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

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

8. 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

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

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

11. Amines IR H-NMR Voodoo Lily Amorphophallus

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

13. Nitro Compounds Typical properties? Classification test: Always do with a known compound to compare! Derivatives (if no other functional group available): Reduce to amine and then prepare amine derivatives Preliminary tests? Solubility Classification tests Derivatives Spectra Iron (II) Hydroxide Test for Nitro Groups Nitro Compounds

14. IR UV MiniQuiz on today’s class Inert Compounds: Alkanes Aromatic Hydrocarbons Alkyl halides Next time:

15. Briefly describe one test (name and result) that would allow you to distinguish between a) an aldehyde and a primary alcohol. b) an alcohol and a phenol. MiniQuiz 7 Questions: