A.

TITLE OF EXPERIMENT
Preparation Of Cyclohexanone

B. AIM OF EXPERIMENT
At the end of the student experiment is expected:
1. Skilled at performing cyclic secondary alcohol oxidation.
2. Can understand the cyclic secondary alcohol oxidation reaction.

C. LITERATURE REVIEW
Cyclohexanone is an organic compound that is an oily liquid and has a
yellow tinge to light and a strong odor. Cyclohexanone is formula C6H10O and
slightly soluble in water and completely soluble with common solvents.
A ketone compound is an organic compound having a carbonyl group
attached to two alkyl groups or two aryl groups, or an alkyl group and an aryl
group. Ketones do not contain hydrongent atoms attached to the carbonyl
group. As with aldehyde compounds, ketone compounds are compounds that
contain an important group in organic chemistry, namely the C = 0 carbonyl
group. All compounds containing this group are called carbonyl 1 compounds.
The carbonyl group is the group that most determines the chemical properties
of ketone compounds. It is therefore not surprising that most of the properties
of ketone compounds are similar to one another, especially with the class of
aldehyde compounds. (Ruslin.2019: 246)
Ketone compounds have functional group isomers with aldehyde
compounds, but aldehyde compounds do not have position isomers like ketone
compounds. Ketone compounds have positional isomers, functional group
isomers, and can even undergo tautomery. A functional group isomer is an
isomer that has the same molecular formula but has a different functional
group. Ketone compounds have functional group isomers with aldehyde and
cycloalkanol compounds. One example of how many isomers of a compound
have the structural formula C5H10O. Compounds with the formula C5H10O
have functional group isomers as aldehyde compounds, cycloalkanols, alkenols
(compounds that have alkene and alcohol groups), and ketones. (Yuanyuan et
al. 2016: 281-282)
Ketone compounds can be classified into several groups based on the
group attached to the carbonyl group, including the following.
1. Aliphatic ketone compounds, in which the two R groups attached to the
carbonyl group are aliphatic chains.
2. An alkyl aryl ketone compound, in which the R group attached to the
carbonyl group consists of an aliphatic chain and an aryl / phenyl group.
3. An aromatic ketone compound, in which the two R groups attached to the
carbonyl group are aryl / phenyl groups.
4. A cyclic ketone compound in which the two R groups are attached to the
carbonyl group is a cyclic ring connected directly by the carbonyl group.

Cyclohexanone
Figure 1. Cyclic ketone compounds

Chemical Reactions of Ketone Compounds Like aldehyde compounds,

ketone compounds can undergo reactions in almost all reactions included in the
reaction categories: (1) carbonyl addition reactions, (2) enol or enolate
reactions, and (3) oxidation-reduction reactions (Ruslin. 2019: 273)
In the reaction of organic compounds, the redox reaction is associated
with the transfer of oxygen and hydrogen. If a compound binds to oxygen or
releases hydrogen, it is said to undergo oxidation, on the other hand, if it binds
to hydrogen or releases oxygen, it is called reduced (Frieda Nurlida, 2000).
 The preparation of cyclohexanone is the oxidation of a cyclic secondary
alcohol to a cyclic ketone by using potassium chromate as an oxidizer in an
acidic atmosphere (Lecturer Team. 21: 17)
Compounds containing the functional group –OH are called alcohols.
The -OH groups are covalently bonded to the carbon atoms in the alcohol
molecules, and the molecules are not oriented in the water to give OH
ions.Alcohol is an organic compound that can undergo oxidation. Based on the
carbon atom that binds the hydroxyl group (-OH), alcohol groups can be
grouped into: primary, secondary, and tertiary alcohols. Primary alcohol is an
alcohol whose OH group is attached to primary C which if oxidized will
produce aldehydes and further oxidation of aldehydes can produce carboxylic
acids. Secondary alcohol is an alcohol whose OH group is attached to
secondary C which when oxidized will produce ketones. Whereas tertiary
alcohol cannot be oxidizedbecause the hydroxyl carrier carbon does not bind
the hydrogen atom. (Putu. 2016)
According to Hart (2009), suggesting that alcohol is classified into
primary (10), secondary (20), or tertiary (30), depending on one organic group
associated with the carbon atom carrying the hydroxyl group.
1. Secondary alcohol oxidation
2. Passes (secondary) alcohol vapor over hot copper.
3. Heating the saturated monocarboxylic acid calcium salt, this
method can be applied to make simple ketones (R-C-R) or ketones.
There are 3 making ketones, namely as follows:Primary alcohols are
oxidized first to aldehydes. Aldehydes are more easily oxidized than alcohols;
therefore, the oxidation usually continues until the carboxylic acid (or, in
alkaline solution, its anion) is formed. Secondary alcohols are oxidized to
ketones in excellent yields by standard oxidizing agents. (Acidic conditions are
usually used because ketones can be oxidized further in alkaline solution.)
Tertiary alcohols are not oxidized under alkaline conditions. If the oxidation is
attempted in acidic solution, the tertian alcohol undergoes dehydration and
then the alkene is oxidized. (Fessenden. 1982: 288-289)
Primary alcohol or secondary alcohol can be oxidized by H2CrO4
chromic acid or by KMnO4. Chromic acid is unstable, therefore it is created
when needed. Na or K-dichromate in acids is a strong oxidizing agent. The
oxidation of alcohol is much better in acidic conditions. Primary alcohols are
oxidized to carboxylic acids, while secondary alcohols are oxidized to ketones.
Chrome is reduced from +6 to +4 which is unstable then changes to +3 (Nurlita
& Suja, 2004).
Cyclohexanone oxime is an important intermediate in chemical
industry, particularly as a key precursor of ε-caprolactam for nylon production
(Chen et al.2014). Usually cyclohexanone oxime is produced from the
condensation of cyclohexanone with hydroxylamine salts, using
hydroxylamine as nitrogen source.
This preparation of cyclohexanone is an example of the oxidation of
alicyclic secondary alcohols to allicyclic ketones with the oxidizing potassium
dichromate under acidic conditions.
Secondary alcohol oxidation. The oxidation reaction of secondary
alcohol compounds can form ketone compounds as shown in the following
reaction scheme in Figure 10.59.

Cyclohexanol Cyclohexanone

The optimum condition for this redox reaction is at a temperature of

55-60 C. Separation and purification of cyclohexanone from this reaction is
carried out based on its physical properties.
 The most common means of ketone synthesis is oxidation of
secondary alcohols. Almost any oxidizing agent can be used. Typical reagents
are chromium oxide (CrO3), Pyridinium Chlor Chromate (PCC), sodium
bichromate (Na2Cr2O7) and potassium permanganate (KMnO4) and NaOCl.