DAT IR spectroscopy, CNMR, HNMR, other lab techniques

IR: C=O

big pointy peak at 1700

IR: OH

large broad trough

far to the left for alcohols

on top of 3000 for carboxylic acids

IR: N-H

one sharp peak around 3200-3500

IR: NH2

two sharp peaks around 3200-3500

IR: CN

medium peak at 2200

IR: NO2

vampire teeth at 1500-1600 and 1300-1400

IR: C=C or C=N

pointy peak at 1600

CNMR: esters, amides, carboxylic acids

160-180

CNMR: aldehydes and ketones

200

HNMR: C=C

4-6

HNMR: benzene

6-8

HNMR: aldehyde

10

HNMR: phenol

10

HNMR: carboxylic acid

12-14

HNMR: amide

11-13

HNMR: OH

.5-5.5

HNMR: amine

.5-5.5

how to extract carboxylic acids

with aqueous NaOH or NaHCO3

how to extract phenols

with aqueous NaOH

how to extract amines

with aqueous HCl

where is the most polar in TLC

towards the bottom, have smaller Rf values

how to increase Rf

add more polar solvent like EtOAc

which is the first to elute in CC

least polar

tollen's test

uses Ag2O to test for aldehydes, makes sides of flask a mirror

iodoform test

uses I2/OH to test for methyl ketones, forms a yellow precipitate

silver nitrate in alcohol test

uses AgNO3 in alcohol to test for alkyl halides, forms a silver precipitate

bromine test

uses Br2, CCl2 tot test for alkenes and alkynes, brown color of bromine disappears

baeyer's test

uses dilute MnO4 to test for alkenes and alkynes, purple solution forms brown precipitate

jones's test

uses CrO3 to test for primary and secondary alcohols, orange reagent turns blue green

lucas's test

uses ZnCl2 to test for secondary, tertiary, and benzylic alcohols, cloudy solution forms separate layers