Name: Angella Rainbow Lim Date Performed: April 29, 2010

Lab Partner: Kevin Villavicencio

EXPERIMENT 10: ALDEHYDES AND KETONES
1. Differentiate the following pair of compounds. Indicate the reagent and the expected visible result.
COMPOUND PAIRS REAGENT EXPECTED VISIBLE RESULT
Phenylethanone Phenylethanol



2,4-DNPH

Phenylethanone will form colored solids,
phenylethanol wont
Butanal

Butanone


Tollens or Schiffs
Reagent or iodoform
Tollens: butanal will form silver mirror,
butanone wont
Schiffs: butanal will give a violet solution
(+) while butanone a light pink color (-)
Benzenecarbaldehyde

Phenylethanal



Benedicts Reagent
Benzenecarbaldehyde: NVR

Phenylethanal: brick red ppt


2-pentanone 3-pentanone I2 in KI solution 2-pentanone forms iodoform, a pale
yellow ppt, while the other compound
gives a negative result
2-pentanol 3-pentanol I2 in KI solution 2-pentanol gives a pale yellow ppt

2. Effect of acid concentration on the rate of addition or formation of ppt of 2,4-DNPH in part F
The typical reaction of aldehydes and ketones is nucleophilic addition to the C=O group and is usually acid-catalyzed. 2,4-DNPH is a
derivative of ammonia, and addition of this is an example of this type of reaction. When the oxygen is protonated, the (+) charge on
the carbonyl carbon is intensified. Hence, a higher concentration of acid will speed up the reaction. But acid concentration must be
controlled; if it becomes very high, the nucleophile will not be as effective due to conversion to an unreactive quaternary ammonium
form, as shown in the mechanism below:





References:
[1] Bailey, P.S. and C.A. Bailey. Organic Chemistry: A Brief Survey of Concepts and Applications. 6
th
ed. Prentice Hall, New Jersey.
2000.
[2] Organic Chemistry Group. Organic Chemistry Laboratory Manual. Institute of Chemistry, UP Diliman. 2008.