Type of Compound

Alcohol

Aldehyde

Ketone

2-butanone

benzaldehyde

2-butanol

2-pentanone

1-pentanol

2-methyl-1-propanal

2-propanone

1-pentanol

2-methyl-1-propanol

2-propanol

trans-cinamaldehyde

acetophenone

1-octanol

cyclohexanone

4-methyl-2-pentanol

Set A Set B Set C

Your unknown will be from one of these sets.

Procedure

Classification Tests

Solid Derivative

Classification Tests

Chromic acid test

Iodoform test

2,4-Dinitrophenylhydrazine test

Chromic Acid TestCrO3/H2SO4 in acetone

H2CrO4Cr3+

red green

Chromic Acid Test

RCH2OH RCOOH

R2CHOH R2CO

RCHO RCOOH

Iodoform TestReagent: NaOH and I2 (NaOI)

CCH3

O

RI2, NaOH

RCOOH + CHI3Yellow

Iodoform Test

CHCH3

OH

RI2, NaOH

RCOOH + CHI3Yellow

2,4-dinitrophenylhydrazine test

NH2NH

NO2

NO2

Aldehyde or ketone

+ NH2NH

NO2

NO2

2,4-dinitrophenylhydrazone

C

O

NH2R C

OH

NHR

NRC

DerivativesAldehydes and Ketones

1. 2,4-dinitrophenylhydrazone

2. Semicarbazone

NH2NHC

O

NH2

semicarbazide

+ RC

O

R NNHCNH2CR

R

O

semicarbazone

Alcohol Derivative

O2N

O2N

C Cl

O

O2N

O2N

C OR

OROH

3,5-dinitrobenzoyl chloride

3,5-dinitrobenzoate

O

CH3CH2CHO

A B C D E

CrO3

+ -B,C A, D, E

DNP+ -

B CA,D E

Iodoform

D A

+

+

-

-