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A106 Organic and

Inorganic Chemistry
Lesson 11: Aldehydes
and Ketones
School of Applied
Science
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Contents
• Introduction of aldehydes and ketones
• Physical properties and synthesis of aldehydes
and ketones
• Mechanism of nucleophilic addition
• Reactions of aldehydes and ketones
• Tests for aldehydes and ketones
• Uses of aldehydes and ketones

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Team Activity (Recap)

A mind map helps to summarize the synthesis and

reactions of alkanes, alkenes, alkyl halides and
alcohols. Identify the reagents used and the type of
reaction (oxidation or reduction) by filling in the boxes in
the attachment below.

Mindmap (Lesson
11)

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Section 1
Introduction of aldehydes and
ketones

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Aldehydes and ketones

• Aldehydes and ketones are organic compounds which

has a carbonyl group, C=O.
R1
C O
R2
Carbonyl carbon

• The carbonyl carbon has two remaining bonds which

are connected to R1 and R2 which can be hydrogen,
alkyl or aryl groups.

• If either R1 or R2 is H (or both), it is an aldehyde.

If both R1 and R2 are alkyl or aryl groups, it is a ketone.
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Aldehydes and ketones

• Aldehydes and ketones have the general formula

CnH2n+1O.

• The first 3 members of the aldehydes are shown

below.

Methanal Ethanal Propanal

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Aldehydes and ketones

• The first 2 members of the ketones are shown

below.

Propanone Butanone

• Why is the first member of ketone: propanone and

NOT methanone or ethanone??

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Sources of aldehydes and ketones

• Aldehydes and ketone are widespread in nature and

are often combined with other functional groups.

• Compounds of plants and

microorganisms containing
aldehydes and ketones include:
 cinnamaldehyde in cinnamon
bark,
 citra in lemongrass,
 vanillin in vanilla bean,
 carvone in spearmint and
caraway,
 camphor in camphor trees.
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Sources of aldehydes and ketones

• Hormones of animal
and human origin
contain aldehydes and
ketones such as:
 muscone in musk deer,
 female sex hormone –
progesterone,
 male sex hormone –
testosterone,
 adrenal hormone –
cortisone

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Section 2
Physical properties and
synthesis of aldehydes and
ketones

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Physical properties

Solubility
• Aldehydes and ketones are soluble in water but their
solubility decreases with increase in the length of the
chain.
• Small sized aldehydes and ketones such as methanal,
ethanal and propanone are miscible with water in
almost all proportions.
• Aldehydes and ketones can form hydrogen bonds with
water molecules and this forms the basis for good
solubility of aldehydes and ketones in water.

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Physical properties
Boiling point
• The boiling point of aldehydes and ketones increases with
increase in the length of the carbon chain.
• Aldehydes and ketones are polar molecules due to the
presence of C=O bond, hence they are attracted by
dipole-dipole attractions (C=O bond) and Van der Waals
forces (alkyl bonds).
• Larger molecules have more electrons which increases
the magnitude of the Van der Waals forces between
molecules.
• The boiling points of aldehydes and ketones will be higher
than similarly sized hydrocarbons with only weak Van der
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Synthesis of aldehydes

Oxidation of alcohols (1o alcohol  Aldehyde)

• Aldehydes can be synthesized from primary alcohols.

PCC

Ethanal
Ethanol
(Primary alcohol)

• This is an oxidation reaction.

• Aldehydes can be further oxidised to carboxylic acids
when strong oxidising agents such as KMnO4 are
used.
PCC: Pyridinium
chlorochromate
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Synthesis of ketones

Oxidation of alcohols (2o alcohol  Ketone)

• Ketones can be synthesized from secondary alcohols.

KMnO4

Propanone
2-propanol
(Secondary alcohol)
• This is also an oxidation reaction.
• Ketones cannot be further oxidised to carboxylic
acids. This is because further oxidation requires
breaking the C-C bond which is stronger than the C-H
bond found in aldehydes.
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Section 3
Mechanism of nucleophilic
addition reaction

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Reactions of carbonyl compounds

• The carbonyl carbon atom is bonded to three other

atoms, hence the carbon is sp2 hybridised.
R1
C O
R2 2
sp hybridised

• The unhybridised 2p orbital of the carbon atom overlaps

with the 2p orbital of oxygen atom to form a  bond.

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Reactions of carbonyl compounds

• The oxygen atom is more electronegative than the

carbon atom, hence the  electrons are pulled
towards the oxygen atom.

• The oxygen atom acquires a partial negative charge

and the carbon atom acquires a partial positive
charge which attracts nucleophiles.

R1 + -
C O
R2

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Reactions of carbonyl compounds

• Carbonyl compounds such as aldehydes and

ketones undergo nucleophilic addition reactions.

• Alkenes having similar overlap of the unhybridised p

orbitals between the two carbon atoms do not
undergo nucleophilic addition reactions.

• The two carbon atoms in alkenes have the same

electronegativity values, hence there is no atom with
partial positive charge to attract nucleophiles.
Instead, alkenes undergo electrophilic addition.
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Nucleophiles (recap)

• Nucleophiles are either fully negative ions, or else

have a strongly - charge somewhere on a
molecule.

• Common nucleophiles are hydroxide ions, cyanide

ions, water and ammonia.
+ + - +
- - -
O H C N O H H N H

hydroxide cyanide + H + H
water ammonia

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Mechanism of nucleophilic addition

Step 1 (Using ethanal and HCN as an example)

• The CN- ion approaches the + carbon and forms a
bond with it.
• The two electrons in one of the bonds joining the
carbon to the oxygen are repelled towards oxygen,
giving it a negative charge.

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Mechanism of nucleophilic addition

Step 2 (Using ethanal and HCN as an example)

• The negative ion formed on the oxygen then picks
up a hydrogen ion from a hydrogen cyanide
molecule forming a cyanohydrin and regenerates
the CN- ion.

cyanohydrin
(2-hydroxypropanenitrile)

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Nucleophilic addition mechanism

[Link]

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Nucleophilic addition

CN- attack from

above will force
CN- attack from above
the existing
groups
downwards.
Molecule X

CN- attack from

CN- attack from below
below will force
the existing
groups upwards.

Molecule Y

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Nucleophilic addition

• Hydrogen cyanide is a very weak acid. It produces

very little hydrogen ions and cyanide ions in the
solution.

• The number of cyanide ions available to attack the

slightly positive carbon is extremely small and so the
reaction would be very slow.

• To increase the rate, the reaction is often carried out

using a solution of sodium or potassium cyanide
(NaCN or KCN) under acidic conditions.
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Nucleophilic addition

• The products formed is an equal mixture of two

optical isomers (racemic mixture).

• Ethanal is a planar molecule, and attack by a

cyanide ion will either be from above the plane of
the molecule, or from below.

• Attack from above will lead to one of the two

isomers, and attack from below will lead to the other.

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Nucleophilic addition
Mirror

Simple rotation
in space

Molecule Y Molecule Z Molecule X

• The rotation of molecule Y in space generates

molecule Z which is a mirror image of molecule X.
• Molecule X and molecule Z are optical isomers.

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Activity 1
Propanone and HCN reacts via nucleophilic addition
reaction.
a) Write the chemical equation for this reaction.
CH3COCH3 + HCN  CH3C(OH)(CN)CH3
b) Draw the mechanism of this reaction.

c) Is the products a racemic mixture? Explain your answer.

No. the product does not contain a chiral carbon

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Section 4
Reactions of aldehydes and
ketones

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Reactions of carbonyl compounds

Oxidation of aldehydes (Aldehyde  Carboxylic acid)

• Aldehydes can be oxidised to form carboxylic acids.

KMnO4

Ethanal Ethanoic acid

KMnO4

Propanal Propanoic acid

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Reactions of carbonyl compounds

Reduction of aldehydes (Aldehyde  1o alcohol)

• Aldehydes can be reduced to form primary alcohols.

LiAlH4

Ethanal

Ethanol

LiAlH4

Propanal
1-propanol
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Reactions of carbonyl compounds

Reduction of ketones (Ketone  2o alcohol)

• Ketones can be reduced to form secondary alcohols.

LiAlH4

Propanone

2-propanol

LiAlH4

Butanone

2-butanol
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Reactions of carbonyl compounds

Reaction with Grignard reagents

• A Grignard reagent has a formula RMgX where X is
a halogen, and R is an alkyl or aryl (based on a
benzene ring) group.

• A typical Grignard reagent might be CH3CH2MgBr.

• The reaction occurs at the C=O double bond, so

aldehydes and ketones react in exactly the same
way.

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Reactions of carbonyl compounds

Reaction with Grignard reagents

• An alcohol is formed from the reaction of aldehydes
and ketones with Grignard reagent.

H+

Aldehyde Grignard reagent

or
ketone Alcohol

• One of the key uses of Grignard reagents is the

ability to make primary, secondary and tertiary
alcohols easily.
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Reactions of carbonyl compounds

Reaction with Grignard reagents

H+

Methanal Grignard reagent

1o alcohol

H+

Ethanal Grignard reagent

2o alcohol

H+

Propanone Grignard reagent

3o alcohol
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Activity 2
Write the chemical equations for the following
reactions.

a) Oxidation of HCHO
HCHO + [O]  HCOOH

b) Reduction of HCHO
HCHO + 2[H]  HCH(OH)H

c) Reduction of (CH3)2CO
(CH3)2CO +2[H]  (CH3)2CH(OH)

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Activity 3

Draw and name the structure of the product formed

when butanone reacts with the Grignard reagent
CH3CH2CH2MgBr.

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Activity 4

Summarize the oxidation and reduction reactions of

alcohol, aldehyde, ketone and carboxylic acid, by
identifying the reagents required in the boxes below.
?

? ?
Alcohol (1 )
o Aldehyde Acid
CH3CH2OH CH3CHO CH3COOH
?

?
Alcohol (2 )
o Ketone
CH3CHOHCH3 CH3COCH3
?
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Activity 4

Answer:

H2CrO4, KMnO4

PCC KMnO4
Alcohol (1o) Aldehyde Acid
CH3CH2OH CH3CHO CH3COOH
LiAlH4

LiAlH4
PCC,
KMnO4
Alcohol (2o) Ketone
CH3CHOHCH3 CH3COCH3
LiAlH4

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Section 5
Tests for aldehydes and ketones

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Tests for carbonyl compounds

• Aldehydes and ketones are a unique class of organic

compounds with the carbonyl group, C=O bond.

• The identification of aldehydes and ketones is based on

addition reaction to the double bond and oxidation
reaction.

• The following tests can be carried out.

 2,4-dinitrophenylhydrazine (2,4-DNPH) test
 Fehling’s test or Tollen’s test (oxidation test, distinguish if
aldehyde or ketone cus aldehyde can be oxidized, ketone cnnt)
 Triiodomethane (iodoform) test

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Tests for carbonyl compounds

.
2,4-dinitrophenylhydrazine test
• Aldehydes and ketones react with 2,4-DNPH to give
a yellow or orange precipitate.

2,4-dinitrophenylhydrazine (Yellow or orange precipitate)

• The yellow or orange precipitate shows the presence

of the C=O double bond in an aldehyde or ketone.
• R1 and R2 can be any combination of hydrogen or
alkyl groups.
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Tests for carbonyl compounds

.2,4-dinitrophenylhydrazine test
• The reaction is known as a condensation reaction.

This gets lost as water and the

other two parts just join together

• A condensation reaction is one in which two molecules

join together with the loss of a small molecule in the
process. In this case, that small molecule is water.
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Tests for carbonyl compounds

.2,4-dinitrophenylhydrazine test
• Examples

Ethanal 2,4-dinitrophenylhydrazine Ethanal 2,4-dinitrophenylhydrazone

Propanone 2,4-dinitrophenylhydrazine Propanone 2,4-dinitrophenylhydrazone

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Testing carbonyls with 2,4-DNPH

[Link]

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Tests for carbonyl compounds

.Fehling’s test
• Recall the difference between aldehydes and ketones.
Aldehydes Ketones

R R1
This can be H C O C O
or alkyl group
H R2

All aldehydes have

hydrogen attached These must be
to the C=O both alkyl groups

• The presence of the hydrogen atom makes aldehydes

very easy to oxidise. Ketones are resistant to oxidation.
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Tests for carbonyl compounds

.Fehling’s test
• Fehling’s solution is a complex compound of Cu2+ in an
alkaline solution.
• When an aldehyde is treated with Fehling’s solution,
Cu2+ is reduced to Cu+ and the aldehyde is oxidised to a
salt of the corresponding carboxylic acid.
• During the reaction, a red precipitate is formed.
RCHO + 2Cu2+ + 5OH-  Cu2O (s) + RCOO- + 3H2O
Aldehyde Copper (I) oxide Salt of
(Red precipitate) carboxylic acid
Fehling’s solution

• Ketones and alcohols do not respond to this test.

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Tests for carbonyl compounds

.
Tollen’s test (Silver mirror test)
• Tollens’ reagent consists of silver ammonia complex,
[Ag(NH3)2]+ in ammonia solution.
• Aldehydes react with Tollens’ reagent to give a grey-
black precipitate or a silver mirror.
• Aldehydes are oxidised to the corresponding acid salt
and the silver is reduced from Ag+ to Ag.

RCHO + 2[Ag(NH3)2]+ + 3OH-  2Ag (s) + RCOO- + 4NH3 + 3H2O

Aldehyde Silver Salt of
mirror carboxylic acid

• Ketones and alcohols do not respond to this test.

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Using Tollens' Reagent to Test for Aldehydes

[Link]

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Tests for carbonyl compounds

Triiodomethane
. test
• Iodine solution is added to a small amount of
aldehyde or ketone, followed by sufficient sodium
hydroxide solution.
• A positive result is the appearance of a very pale
yellow precipitate of triiodomethane, CHI3.
• The pale yellow precipitate of triiodomethane
(iodoform) is given by an aldehyde or ketone
containing the group, CH3CO–.
CH3
This can be H C O
or alkyl group
R
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Tests for carbonyl compounds

Triiodomethane
. test
• Overall equation for this reaction:
CH3
C O + 3I2 + 4OH-  CHI3 + RCOO- + 3I- + 3H2O
R Iodoform
Aldehyde or (pale yellow
ketone precipitate)

• Ethanal is the only aldehyde to give a positive result.

• Ketones that give a positive result for this reaction
have a methyl group on one side of the carbon-
oxygen double bond. These are known as methyl
ketones.
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Activity 5
The structure of organic compounds X and Y are
shown below.

O O

C2H5 C H C2H5 C CH3

Compound X Compound Y
Determine whether a positive or a negative result will
be obtained upon treating them with:
a) 2,4-DNPH (X- positive, Y- positive)
b) Fehling’s solution (X- positive, Y- negative)
c) Alkaline aqueous iodine (X- positive, Y-positive only
for methyl ketones)
Explain your answer.
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Activity 5

O O

C2H5 C H C2H5 C CH3

Compound X Compound Y

Compound X Compound Y
Positive (X is an Positive (Y is a
2,4-DNPH
aldehyde) ketone)

Positive (X can be Negative (Y cannot

Fehling’s solution
oxidised) be oxidised)

Alkaline aqueous Negative (X does Positive (Y

iodine not contain a contains a
CH3CO- group) CH3CO- group)

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Activity 6

Summarize the tests for aldehydes and ketones by

identifying whether they give a positive or negative
reactions with the testing reagents in the boxes below.

Aldehyde Ketone
RCHO R1R2CO

Fehling’s Alkaline Fehling’s Alkaline

2,4- 2,4-
solution or aqueous solution or aqueous
DNPH DNPH
Tollens’ reagent iodine Tollens’ reagent iodine

? ? ? ? ? ?

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Activity 6

Aldehyde Ketone
RCHO R1R2CO

Fehling’s Alkaline Fehling’s Alkaline

2,4- 2,4-
solution or aqueous solution or aqueous
DNPH DNPH
Tollens’ reagent iodine Tollens’ reagent iodine

Positive Positive Negative for Positive Negative Positive for

because it because it can all aldehydes because it because it only methyl
contains a be oxidised to a except for contains a cannot be ketones
C=O double carboxylic acid CH3CHO (R C=O double further oxidised (either R1 or
bond is CH3) bond R2 is CH3)

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Section 6
Uses of aldehydes and ketones

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Uses of aldehydes
H
Formaldehyde C O
(Methanal)
H

Used in tanning, Reacts with Dissolves in water

preserving and phenol to form (37%) to form
embalming and as Bakelite which formalin which is
germicides, insecticides is used in used as an
and fungicides for plastics coating antiseptic and
plants and vegetables. and adhesives. disinfectant.

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Uses of aldehydes

•. Other aldehydes of industrial significance

O
are acetaldehyde and benzaldehyde.
H3C C
• Acetaldehyde is largely used for the H
production of acetic acid and pyridine Acetaldehyde
derivatives.
O H
C
• Benzaldehyde is used in perfumes,
cosmetic products, and dyes. It is added
to provide almond flavour to food
products and also used as a bee
repellent. Benzaldehyde
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Uses of ketones
O
H H
Acetone C
(Propanone) C C
H H
H H

Used in Used in Use in

industry as a household as medicine in
solvent and a nail polish chemical
cleaning remover and peeling and for
agent. paint thinner. acne treatment.

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Uses of ketones

•. Other ketones of industrial significance

are methyl ethyl ketone (MEK), also O
known as butanone and cyclohexanone. H
C
H
H
C C
H C
• MEK is used as a commercial cleaner H H H
H
and solvent for glues, paints, coatings, MEK
and printing inks.
O

• Cyclohexanone is an important chemical

solvent used in a variety of industries, in
particular, the paints and printing
industry. Cyclohexanone
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IT’S TIME FOR

1. Go to “[Link] on your laptop or mobile phone.
2. Enter Game PIN generated by your lecturer.
3. Choose your Nickname and Get Ready!
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Learning outcomes
• Name aldehydes and ketones using IUPAC
nomenclature.
• Describe the formation of aldehydes and ketones
from primary and secondary alcohols respectively.
• Describe the reactions of aldehydes and ketones
including oxidation, reduction and with Grignard
reagents.
• Describe the mechanism of the nucleophilic addition
reactions of hydrogen cyanide with aldehydes and
ketones.

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Learning outcomes
• Explain the differences in reactivity between carbonyl
compounds and alkenes towards nucleophilic
reagents.
• Describe the use of 2,4-dinitrophenylhydrazine (2,4-
DNPH) to detect the presence of carbonyl compounds.
• Deduce the nature (aldehyde or ketone) of an
unknown carbonyl compound from the results of
Fehling’s and Tollens’ reagents.
• Deduce the presence of a CH3CO– group in a carbonyl
compound from its reaction with alkaline aqueous
iodine to form tri-iodomethane.
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Further reading
1. Oxidation of Aldehydes and Ketones - Chemistry
LibreTexts
2. Preparation of Aldehydes and Ketones - Chemistry
LibreTexts
3. Reactions with Grignard Reagents - Chemistry
LibreTexts
4. [Link]
[Link]
5. [Link]
ketones/

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