Organic Chemistry Lab

Front 1

2,4 DNP Test

Back 1

For Aldehydes and Ketones
(+) precipitate formation
carbonyl --> imine

Front 2

Tollens Test

Back 2

For Aldehydes
(+) Formation of a silver mirror or black precipitate
Hydrogen of aldehyde --> O-

Front 3

Iodoform Test

Back 3

For methyl ketones
(+) Formation of yellow ppt (iodoform)
methyl group --> O-

Front 4

Hinsberg Test

Back 4

For Amines
1 - dissolves in base and precipitates from acid
2 - precipitates from base and no change in acid
3 - precipitates from base and dissolves in acid

Front 5

The Lucas Test

Back 5

For Alcohols
(+) haziness
1 - no reaction
2 - 5 - 10 minutes
3, allylic, and benzylic - immediate to 2-3 minutes
alcohol is replaced with chlorine (substitution)
complication --> must be no more than 6 carbons

Front 6

Iron Chloride Test for soluble phenols

Back 6

(+) color change
complication --> carbonyl with high enol can give false positive
Fe(OAr)3 is a colored complex

Front 7

Iron Chloride Test for insoluble phenols

Back 7

only difference is the addition of pyridine
(+) color change

Front 8

Bromine Water Test

Back 8

For phenols
(+) discharge of bromine color
complication --> aromatic compound with activating substituents can give false positive

Front 9

Iron Hydroxide Test

Back 9

For nitro
(+) red-brown precipitate
(-) greenish precipitate
ferrous hydroxide --> ferric hydroxide through oxidation
complication --> not as accurate can be false positive for other halides

Front 10

The Beilstein Test

Back 10

For halides
(+) greenish flash
complication --> cannot detect fluoride because not volatile

Front 11

Bromine in Methylene Chloride

Back 11

For double/triple bonds
(+) discharge of the bromine color
complication --> electron withdrawing groups int he vinylic position slows down reaction
complication --> false positive can occur with substitution instead of addition

Front 12

The Chromic Acid Test

Back 12

For 1 & 2 alcohols and aldehydes
(+) blue green color
reduction of chromium (IV) --> chromium (III)
oxidation of 1 alcohol --> aldehyde --> carboxylic
oxidation of 2 alcohol --> ketone

Front 13

Soluble in Water

Back 13

litmus paper blue --> basic (low MW amines)
litmus paper red --> acid (low MW carboxylic acid)
litmus paper unchanged --> neutral (low MW neutral)

Front 14

Insoluble in Water, Soluble in NaOH

Back 14

soluble in NaHCO3 --> strong acid (carboxylic acid & phenol)
insoluble in NaHCO3 --> weak acid (phenols)

Front 15

Insoluble in Water, Insoluble in NaOH, soluble in HCl

Back 15

base (amine

Front 16

insoluble in water, insoluble in NaOH, insoluble in HCl, soluble in H2SO4

Back 16

neutral compound (alkenes, alkynes, alcohols, ketones, aldehydes, nitro, ester, ether, amine)

Front 17

Insoluble in all

Back 17

inert compound (alkanes, alkyl halides, aromatic compound)

Front 18

Benzoin condensation

Back 18

2 benzaldehyde to form 1 benzoin through condensation
catalyzed with CN-

Front 19

Oxidation of Benzoin

Back 19

1 benzoin --> 1 benzil through oxidation
catalyzed with HNO3

Front 20

Aldol Condensation

Back 20

Benzil + dibenzyl ketone --> tetraphenylcyclopendtadiene through aldol condensation and then dehydration
solvent is NaOEt

Front 21

solid/solid separation

Back 21

Acid/Base Extraction
Extraction with NaHCO3 (weak base) --> remove strong acids
Extraction with NaOH (strong base) --> remove weak acids
Extraction with HCl (strong acid) --> remove base
methylene chloride used to drop the organic layer to the bottom

Front 22

liquid/liquid separation

Back 22

Fractional Distillation
cannot be used if boiling points are close