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Carbonyl summary Summary of Organic Reactions (VI.

Carbonyl compounds)
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VI.
A. 1.

Carbonyl compounds
Nucleophilic addition Reaction with hydrogen cyanide
O + HCN
R C R

O H
R C R

2.

Reaction with sodium hydrogensulphate(IV)


R
O C
+ Na HSO3 +

R
H O C

SO3 Na

CH3/H

CH3/Hwhite precipitate

Note:

1. Sensitive to steric hinderance and reacts with aldehyde and methyl ketone only. 2. Can be used to purify aldehyde or methyl ketone.

B. 1.

Addition-elimination (condensation) Reaction with hydroxylamine


O + R C R H hydroxylamine H N OH R C N R oxime (white ppt.)
OH + H2O

Note : 1. A test for aldehyde or ketone. 2. Identify the carbonyl compound by characterization.

2.

Reaction with 2,4-dinitrophenylhydrazine


R O
C+

H H H N N O2N

R NO2 R

H C N N O2N NO2 + H2O

2,4-dinitrophenylhydrazine

2,4-dinitrophenylhydrazone (orange ppt.)

Note : 1. Test for aldehyde or ketone but no reaction with carboxylic acid and its derivatives 2. Identify the carbonyl compound by characterization.

3.

Triiodomethane formation
O H
R C C H

NaOH(aq) + I2(aq)
R

O
C + H

I
C I

H methyl ketone

O I carboxylate iodoform ion (yellow ppt.)

Note : 1. Test for methyl ketone. 2. Shortens the carbon chain by 1 C

Summary of Organic Reactions (VI. Carbonyl compounds)


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C. 1.

Oxidation and reduction Oxidation of aldehyde with potassium dichromate(VI)


O R
C

[O] H R

O
C

OH

aldehyde

carboxylic acid

Note : Orange acidified potassium dichromate will turn to green chromium(III) ion.

2.

Oxidation of aldehyde with Tollens' reagent


O O Tollen's reagent + R C H R C O NH4 + Ag(s) aldehyde [Ag(NH3)2]OH(aq) ammonium silver mirror carboxylate

Note : Test for aldehyde

3.

Oxidaton of aldehyde with Fehling's reagent


O R C H aldehyde Fehling's reagent
O

Cu2O brick red ppt.

R C O- + carboxylate ion

Note : Test for aldehyde

4.

Resistance of ketones to oxidation


O R C R [O] no reaction

Note : Ketone is stable to general oxidation.

5.

Reduction with sodium tetrahydridoborate / lithium tetrahydrioaluminate


O
-

O
+ NaBH4(aq)

H3 O
R C R/H R/H

+
R

O
C

H
R/H

aldehyde or ketone O
+ LiAlH4(ether)

H alkoxide O
R C

H alcohol H3O
R/H

+
R

O
C

H
R/H

R/H

aldehyde or ketone

H alkoxide

H alcohol

Note : LiAlH4 cannot be used in aqueous medium.

6.

Haloform reaction
O H
R C C H

NaOH(aq) + I2(aq)
R

O
C + H

I
C I

H methyl ketone

O I carboxylate iodoform ion (yellow ppt.)

Note : 1. Test for methyl ketone. 2. Shorten the carbon chain by 1 C.

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