NAME Shahriar Shemo BATCHJan 28

SCHOOL ID 16780

EdexcelA Level Unit 4 NOTE Organic

CHEMISTRY

Carbonyl Compounds
(Aldehyde & Ketone)
CMd klamum LL Rashid
Chemistry Teacher
Cambridge Edexcel
OA Levels
01675240922, 01853605525
The Periodic Table of Elements
0 (8)
(18
1.0 4.0
H He
hydrogcn heili
Key (13) (14) (15) (16) (17)
6.9 9.0 relative atomic mass 10.8 12.0 14.0 10.0 19.0 20 7
Li Be atomic symbol B C N F Ne
raree boron carbon nrogen 0XYSen luorine
alom (pr otpn) iuinter 6 7 8 9 10
72.0 24.3 27.0 28.1 31.0 32.1 35.5 39.9
Na Mg Al Si P S CI Ar
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11 12 (4) (6) ( (10) (11) (12 D 15 17

9.1 40.1 45.0 47.9 50.9 72.6 74.9 79.0 9.9 3.8
52.0 54.9 55.858.9 58.763.565.4 69.7
K Ca SC Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge AS Se Br Kr
Cobalt Chel opper gailtui Sermanum arseon e l e u n | Droie
19
22 23 24 27 J0 2
8%.5 87.6 88.9 91.2 92.9 95.9 98 101.1 102.9106.4 107.9 112.4 114.8 118.7 121.8 127.6126.9 1313
Rb Sr Y Zr Nb Mo TC Ru Rh Pd Cd In Sb le Ke
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nium nbudvoe techuetsn ruthenum rhodum pailadiusiver cadm umdium antimiony| tellun odr1e
39 40 41
42 43 44 4 6
47 50 51 52
32.9 13/.5 8.1 /8.5
180.9 83.8 186.2 190.2 192.2 195.1197.0 200.6 201.4207.2 209.0 209) (210] 222
CsBa La* Ht W Re Pt Au Hg Bi Po Rn
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223 |226) 227] 261 [262] [266) ?64] [277) 268] (271] 272)
Fr Ra AC" R DD Sg Bh Hs Mt Ds Rg Elements with atomic nunbers 112.116 have been repor ted
r e m rac'um ar tistuth ndie*1zdu|dubntum iscabor gium| toriLim hassium ineierun damsunrantym but not fully authentucated
87 89 104 105 106 107 108 109 110 111
2P age
Carbonyl Compounds:
A carbonyl compound is a compound which has a carbon atom bonded to an oxygen atom by a double hon.l te

(C=O).
Compounds having carbonyl group as functional group are carbonyl compounds.

Note:

Carbonyl compounds contain carbonyl group where oxygen atom is more electronegative than carbon, so the shared

electrons are slightly shifted towards oxygen making it slightly negative (6) and carbon atom slightly positive (6").

=O

Polar nature of the bond makes the carbon atom

to be attacked by Nucleophile. So carbonyl compounds give
Nucleophilic addition reaction.

Classification of carbonyl compounds:

1. Aldehyde

R~CO H

2. Ketone

e O

Naming Aldehyde: nchoral group-CHo (-e

Aliphatic aldehyde: H-CHO H e methanal /methyl aldehyde

CH-CHOHa-CH ethanal/ ethyl aldehyde

CH-CH2-CHO O propanal / propyl aldehyde

H- - e CH
Aromatic aldehyde or aryl aldehyde:
CHO
Colls-eHO ben2oldehpde

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Md. Mamun Ur Rashid, Chemistry Teacher,
 Pae 13
Naming ketone: funthional groupe0-(-e
Aliphatic ketone: CH-CO-CH3 -e propanone
~CH
CH3-CO-CH2-CH3 butanone

CH3-CH2-CO- CH-CH3 pentan 3-one

CH3-CO-CH2-CH2-CH3 pentan-2-one

Aromatic ketone:
bengophe none

O-CO0
CH3- phenplethanone

Physical properties of carbonyl compounds:

1. Types of intermolecular forces of attraction:

Dispersion force

and permanent dipole dipole attraction.

-

(due to Polar C-O bond)

Note:

(a) Alcohol: All 3 types of intermolecular forces of attraction.

Dispersion forces, permanent dipole-dipole interaction and hydrogen bonding

permanent dipole - dipole attraction.

(b) Aldehyde: Dispersion force and

permanent dipole - dipole attraction.

(c) Ketone: Dispersion force and

(d) Carboxylic acid: All 3 types of intermolecular forces of attraction.

Dispersion forces, permanent dipole - dipole interaction and hydrogen bonding.

Q. Methane, methanol, methanal, methanoic acid. Arrange them in order of increase in boiling points.

Ans: Hethone Kmethan al nethano) methanoie acid

Q. Propane, Propanol, Propanone, Propanoic acid. Arrange them in order of increase in boiling points.

Ans:
aCd
Pro ponepropanone Proponol po panoie

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41age
Q. Both 2-methylpropanal and butanal are isomers of each other.
2-methylpropanal boils at 64'C whe
butanal boils at 72°C. Explain why?
Ans:

CH-CH-OHO l3-CH,-Ct, -CHO

-hedhpl psoponol bufo nal
Branched chain isomers have lower
boiling points than that of straight chain isomers. Because straight chain
isomers can pack closer together than the branched chain isomers, which means the dispersion forces
between the molecules of straight chain isomers are
stronger than those between molecules of branched
chain isomers.

Note:
eug-CH2-Cll2 -Co -CHs Ha-eH l0-eH
Pentan-2-one 2-me4hplbutonone

Pentan-2-one boils at 102°C whereas 3-methylbutanone boils at 94°C.

2. Solubility of Aldehydes and ketones:

Smaller molecules of aldehydes and ketones soluble in water. For

are example, methanal, ethanal and propanal
are miscible with water in all proportions but the solubility decreases with increase in carbon chain length
Reason:

The reason for solubility is that they can form hydrogen bonds with water molecules even though they cannot

form hydrogen bonds among themselves.

R C=O 104.S+

Note Aldehydes can form hydrogen bonds with water molecules

though they cannot form hydrogen bonds among themselves.

Ma Mammuwur Rashid, Chemistry Teacher, Cell: 01675240922, 01853605525

 bonds
Smaller molecules of ketones do not form hydrogen bonds among themselves but they form hydrogen

the
with water molecules. As carbon chain length increases, the hydrocarbon portions of the molecules prevent

formation of hydrogen bonds. -

st 4
Ho45

20

Note: Aldehydes are more soluble in water than ketones

because ketones have more alkyl groups.

Preparations of Aldehydes and ketones:

aid
Note:
o eenr boxyplie
1alasho oldohtde
ketone
aleohal

Preparing Aldehyde:

be produced. It can be separated by

(1) By oxidation of primary alcohol with acidified oxidizing agent, aldehyde can

fractional distillation.

If the aldehyde is not removed after formation, it will be further oxidized to carboxylic acid.

Aldehyde has lower boiling point (b.p.) than its respective alcohol and acid. So it can be separated by fractional

distillation.

(2) Aldehyde can also be prepared by reduction of carboxylic acid.

Md Mamunur Rashid, Chemistry Teacher, Celu 01675240922, 01853605525

61Fae
Reduction is carried out by reducing agent such as

LiAIHA (Lithium tetrahydridoaluminate or Lithium aluminium hydride)

or NaBH (Sodium tetrahydridoborate or Sodium borohydride)

Note:

i) LiAlH is dissolved in dry ether (ethoxy ethane or diethyl ether).

(i) NaBH is dissolved in dry ethanol

Preparing ketones:

By oxidation of secondary alcohol with acidified oxidizing agent using heat under reflux, ketone can be

prepared which is then separated by fractional distillation.

Identification of Carbonyl Group:

Carbonyl groups can be identified by adding Brady's reagent (2,4-DNPH)

H H
H

H
N-NH NO2 H
N -N ND2
Phenpl
Hpdrozin 2-4- dinitropheapl
NO2
2,4- DINito Pheny
Hpelr7ine

(2,4-DNPH)
Brady's reagent is a red-orange solid.

Test: Aldehydes and ketones (carbonyl compounds) react with Brady's reagent (2,4-DNPH)

to form yellow or orange or red crystalline solids by condensation reaction (elimination of water)

Reaction with Aldehyde:

H

-N NO l N-N
H

HO2

aldehpde aldehyde hpdro2one

Ma Mamun ur Rashid, Chemistry Teacher, Cell: 01675240922, 01853605525

Keaction with Ketone:
17
H

+
N NO2
C N-N NO2

Ketone Ketone Hpdra2one

The product from the reaction between carbonyl compound and 2,4-DNPH is a crystalline solid (hydrazine
derivative).
The derivative is separated by filtration and purified by recrystallization. Each derivative has characteristic melting

temperature which can be compared to the values given in the data booklet.

Carbonyl compound Melting temperature of 2,4-DNPH derivative (°C)

Methanal 166

Ethanal 168

Propanal 155

Propanone 126

Butanone 115

Note

(1) Brady's reagent is supplied wet to reduce the risk of explosion.

(2) Other reagents can also be used to identify carbonyl group. They are:

() Hydrazine (H;N-NH2)

(i) Hydroxylamine (NH-OH)

(ii) Dinitrohydrazine

(3 Brady's reagent is more useful than any other reagents to test carbonyl compounds because derivatives

made from Brady's reagent are less soluble and therefore crystallize out more easily.

Note: However more sophisticated techniques such as infra-red spectroscopy is used to identify derivatives.

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 8Page
Recrystallization
It is used to purify a solid material by removing both soluble and insoluble impurities.

NOTE:

1. Insoluble impurities are removed by hot filtration.

2. Soluble impurities are removed by cold filtration.

3 A solvent is chosen where solubility of solid increases with

temperature and the substance must be

easily soluble in hot solvent and much less soluble at room temperature.

Procedure:

1. The solid is dissolved in minimum volume of

hot solvent in order to make a saturated solution.
2. Filter the hot mixture through a preheated filter funnel, it removes insoluble impurities.

NOTE: Hot funnel is necessary to Solute

prevent the soluble crystallizing and blocking the funnel.
In order to make filtration faster, it is carried out
using Buchner funnel under reduced pressure. (Vacuum

filtration)
3. Cool the hot filtrate, solute will
so
crystallize.
4. Filter the cold mixture using Buchner funnel under reduced
pressure.

5. Wash the remaih

crystals with small amount of cold solvent, it removes any impurity reaming-on the surface of crystals.
NOTE: A small amount of cold solvent is used so that the crystals are not washed away/ do not dissolve.
6. Crystals are then dried on the filter paper and placed inside a desiccator or oven. It is better to dry crystals in a

desiccator than heating in an oven because some solids decompose at higher temperature.

Vacuum Filtration:

Filtration under reduced pressure is vacuum filtration. Reduced pressure is achieved by using a suction pump.

This filtration is faster. It is

mainly used to remove soluble impurities.
Guchner onnel
ilte
Poper

Vocubm
Side-ar m Pump

flask

Md Mamunur Rashid, Chemistry Teacher, Cell 01675240922, 01853605525