Beruflich Dokumente
Kultur Dokumente
BACKGROUND
The major similarity between an aldehyde and
a ketone is the carbonyl group. A carbonyl
group is a carbon atom doubly bonded to an
oxygen atom, as depicted below.
..O..
C
..O..
..O..
R C H
Aldehyde
R C R'
Ketone
[O]
R C
[H]
[O]
R C O H
aldehyde
[H]
carboxylic acid
primary alcohol
O H
R C
H
[O]
O
R C
[H]
[O]
N.R.
ketone
[H]
secondary alcohol
O
R C H
H+ and
R'-OH
R C R'
H+ and
R''-OH
OH
OR"
OR"
hemiketal
(intermediate)
ketal
alcohol
ketone
H2O
OR"
R C R'
R C R'
R" O H
H2O
acetal
hemiacetal
OR'
OR'
alcohol
aldehyde
OR'
R C H
R C H
R' O H
C H
2 Ag(NH3)2OH
aldehyde
O
2 Ag (s)
H2O
3 NH3
black ppt or
silver mirror
C CH3
+ 3 I2 +
4 NaOH
alpha
methyl
ketone
O
R
+ 3 NaI +
C
O Na
3 H2O
CHI3 (s)
yellow
Chemical Tests
Five tests will be used in this experiment.
1. Iodoform test
2. Bordwell test (Chromic acid test)
3. Tollens test
4. 2,4-DNP test
5. Purpald test
Both chromic acid and Tollens reagent are
used to differentiate between aldehydes and
ketones. Aldehydes are oxidized relatively
easily, while ketones are not easily oxidized.
Chromic acid Test (Bordwells Reagent or
Jones reagent)
The chromic acid (CrO3) will change in color
from orange to brown to green/blue when it
oxidizes an aldehyde. It should stay an orange
solution if it is not. Note: A negative result of
this test will not tell you if you have a ketone,
it only tells you that you do not have an
aldehyde.
NH2
NH
NH
O
C
R1
H2SO4
O2N
NO2
2,4-DNP
R2
alcohol
R2
aldehyde
or ketone
O2N
H2O
NO2
red ppt
O
3R
C H
aldehyde
2 CrO3
3 H2SO4
orange
O
3 R
C OH
carboxylic
acid
3H2O
Cr2(SO4)3
green
O
R CH
aldehyde
HS
NH2
NH2
NH
C
O2 (air)
HS
Purpald
(colorless?)
purple color
3 H2O
EXPERIMENTAL PROCEDURE
CAUTION! Chromic acid is very corrosive and
any spills should be immediately flushed with
water. Use gloves with these reagents.
Dispose of reaction mixtures and excess
reagents in waste containers only as directed
by this handout or your instructor.
1. Your observations are the most important
aspect of this lab. Remember to be as
descriptive as possible and highly organized.
Carefully record all observations in the data
tables. For each test you will use 5 tubes:
Tube 1 butanal
Tube 2 acetone
Tube 3 unk A
Tube 4 unk B
Tube 5 unk C
Test 1, Iodoform Test
2. Take 5 test tubes. In tube 1 add 5 drops of
butanal, tube 2: 5 drops of acetone, tube
3: 5 drops unk A, tube 4: 5 drops unk B,
and in tube 5: 5 drops of unk C.
3. Add 1 mL of H2O to each tube.
4. To each test tube, add 0.5 mL of 10% NaOH
(which may be labeled as 3M NaOH).
5. Add 10 drops of the I2-KI test reagent (may
be labeled Iodoform) while shaking.
6. Examine the tubes for a yellow (not white)
precipitate (ppt). Set them aside and
examine them again after youve
completed the other tests; formation of the
precipitate can be slow.
7. At the end of the period, discard the waste
in the organic waste container. Rinse with a
small amount of acetone, and place the
rinse in the halogenated waste container.
Then wash the test tubes with soap and
water.
Test 2, Chromic Acid (Jones Reagent))
8. Use 5 clean test tubes. In tube 1: add 5
drops of butanal, tube 2: 5 drops acetone,
etc. (as before in step 2))
9. To each test tube add 3 drops of Chromic
Acid Reagent (Jones Reagent or Bordwells
Reagent) and agitate (by flicking the tube
with your finger). Note any color changes
and note any temperature changes.
10. Discard all waste in the chromium/organic
waste container. Rinse your test tubes with
a little acetone and discard the rinse in the
chromium/organic waste container. Then
wash the tubes with soap and water.
Lab Report:
Pre-lab
On a separate paper write your title, purpose
and name
During lab
Fill in your data table.
Use the models to make the acetals and ketals
on the acetals and ketals worksheet at the
back of the lab.
Post-lab
(You can start your analysis on the front of the
title page)
Analysis: Explain how you identified each of
your unknowns as either an aldehyde, a
methyl ketone, or neither. Be specific,
explaining the purpose of a negative test as
well as a positive test.
Draw the structures forany two aldehydes and
any two two ketones and name each.
Discussion: Restate the identities of your
unknowns. Explain the utility of each test.
Name__________________________
4. 2,4-DNP Test
Tests for: aldehydes and ketones
Compound
Observations
Observations
Draw the initial butanal and one methanol you did above then combine the models to form the
hemiacetal .
Draw the reaction below and the picture of the model above. (step 3 next page)
Start with the hemiacetal you drew above and then draw the second alcohol then combine them together
to form the full acetal and show the water released. Draw the reaction below and the picture of the
model above. (step 4 next page)
Start with the hemiketal and react it with a second alcohol to make the full ketal and show water
released.
Draw it (step 4 next page)
Break here
(at H)
O
R
C H
aldehyde
H O R"
O H
C H
first
alcohol
R C H
R"
O R"
hemi-acetal
=hole
Break here
(at C)
O H
O H
H
O H
R C H
O R"
hemi-acetal
H O R"
second
alcohol
C H
O R"
R"
O R"
R C H
=hole
O R"
acetal
In the bottom half of the paper you will repeat this procedure with 2-butanone first to form the hemi
ketal with the first alcohol. Then starting with the hemiketal you will form the full ketal using the
second alcohol.
10