Today: Unknown 1 (review) aldehyde, ketone, alcohol, phenol

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Presentation transcript:

Today: Unknown 1 (review) aldehyde, ketone, alcohol, phenol carboxylic acid, ester, anhydride, amide, amine (Cl, Br, nitro) Questions?

Classification Tests for Aldehydes and Ketones Preliminary tests Solubility Classification tests Derivatives 2,4-dinitrophenylhydrazone (2,4-DNP) also a good derivative! →Prepare two good derivatives of each unknown if possible. Recrystallize from ethanol/water.

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

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

Alcohols and Phenols Solubility distinction! Preliminary tests Solubility Classification tests Derivatives Spectra Alcohols and Phenols Solubility distinction! Solubility: Alcohols: “neutral”; Phenols: very weak acids, pKa around 10, except nitrophenols! Classification tests: Jones (positive for 1o, 2o alcohols, aldehydes, amines…!) Lucas test for 3o alcohols, 2o alcohols (slow): Phenols only: Complexation with Fe 3+

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

Refractive Index (confirming liquid unknowns) 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.

carboxylic acid, ester, anhydride, amide, amine (Cl, Br, nitro) Unknown #2: carboxylic acid, ester, anhydride, amide, amine (Cl, Br, nitro) Functional groups?

Preliminary test results? Preliminary tests? Solubility Classification tests Derivatives Spectra Carboxylic Acids Anhydrides Esters Amides Amines Nitro 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?

What type of information do you get if your unknown 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?

Carboxylic Acids Good mp.s (consider recrystallization) Solubility Classification tests Derivatives (not done) Spectra Carboxylic Acids Good mp.s (consider recrystallization) Neutralization Equivalent (titration) experimental instructions on our webpage RCO2H + NaOH RCO2(–) Na(+)aq. + H2O Derivatives (we do not do them in the lab): Convert carboxylic acid into acid chloride first, then into amides 1. + HCl 2. Define carboxylic acid by: mp., neutr. equivalent, an ester and its bp.

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

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

Amine Derivatives Amines in plant odors … : 1. Picrates Preliminary tests? Solubility Classification tests Derivatives Spectra 1. Picrates 2. Benzamides: amine + benzoyl chloride NH 2 OH NO O N + Amines in plant odors … : Voodoo Lily Amorphophallus

Alkanes Aromatic Hydrocarbons Alkyl halides MiniQuiz on today’s class Next time: Conclusion Unknown 2 Inert Compounds: Alkanes Aromatic Hydrocarbons Alkyl halides UV spectra MiniQuiz on today’s class