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

EstersAmines

(Unknown #2)

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• Mp. (range!) for solids

• Bp., refractive index for liquids

• Ignition test

• Test for unsaturation

• Beilstein test for halogen (p.626)

Preliminary 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?

Solubility Tests (pp. 626 – 627)

Aldehydes and Ketonesfunctional group?

•Typical properties? Mp.? Bp.?

• Solubility?

• Preliminary tests

• Solubility

• Classification tests

• Derivatives

• Spectra

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

• 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

Aldehydes and Ketones Derivatives

Imines:2,4-dinitrophenylhydrazone

oximesemicarbazone

• Preliminary tests

• Solubility

• Classification tests

• Derivatives

• Spectra

• 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….

Aldehydes and Ketones

IR:

H-NMR:

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 3o alcohols, 2o alcohols (slow):

• Phenols only: Complexation with Fe 3+

• Preliminary tests

• Solubility

• Classification tests

• Derivatives

• Spectra

Anthocyanin Colors

- glucose

Cl-

O

O

OH

HO

OH

OCH 3

OCH 3

+

Malvidinan anthocyanin in blue grapes

Alcohol and Phenol Derivatives

• with 3,5-dinitrobenzoyl chloride

• urethanes

Similarly: Naphthyl urethanes

Phenols only: Bromoderivatives

• Preliminary tests

• Solubility

• Classification tests

• Derivatives

• Spectra

Alcohols

IR:

H-NMR:

Exchange with D2O

• Preliminary tests

• Solubility

• Classification tests

• Derivatives

• Spectra

Phenols

H-NMR

IR

Next time:

• Carboxylic Acids and Esters

• Amines

Review this class!