Ozonolysis of Alkenes and Alkynes-Mechanism

What is Ozonolysis?

Oxidation of alkenes with the help of ozone can give alcohols, aldehydes, ketones, or carboxylic acids.

Alkynes undergo ozonolysis to give acid anhydrides or diketones. If water is present in the reaction, the acid anhydride undergoes hydrolysis to yield two carboxylic acids.

Ozonolysis of elastomers is also known as ozone cracking. Trace amounts of ozone gas in the atmosphere cuts the double bonds in elastomers. For azo compounds, the ozonolysis yields nitrosamines.

Ozonolysis Reaction

Ozone is a very reactive allotrope of oxygen. The reaction of ozone with alkenes and alkynes causes the oxidative cleaving of the alkene or alkyne. The carbon-carbon triple bonds are replaced with carbon-oxygen double bonds, giving the required carbonyl product as shown below.

Ozonolysis refers to the organic chemical reaction where ozone is employed to cleave the unsaturated bonds of alkenes, alkynes, and azo compounds (compounds with the functional diazenyl functional group). It is an organic redox reaction.

Ozonolysis Mechanism

The Ozonolysis mechanism proceeds via an oxidative cleavage reaction.

The ozone not only breaks the carbon pi bond but also the carbon-carbon sigma bond. It involves the attack of ozone on the given reactant to form an ozonide. To eliminate the oxygen in this intermediate stage, zinc dust is employed (since it forms zinc oxide with oxygen).

The final product varies based on the type of reactant and the workup. Given below is an illustration depicting the general mechanism of the ozonolysis reaction for alkenes and alkynes.

Ozonolysis refers to the organic chemical reaction where ozone is employed to cleave the unsaturated bonds of alkenes, alkynes, and azo compounds (compounds with the functional diazenyl functional group). It is an organic redox reaction.

Ozonolysis of Alkenes

Alkenes can undergo ozonolysis to form alcohols, aldehydes, ketones, or carboxylic acids.

The general procedure uses a solution of alkene in methanol. Ozone is bubbled through this solution at approximately 780 Celsius. When the solution turns blue, the alkene is consumed (the blue colour comes from the unreacted ozone).

Other indicators of the endpoint of the reaction include potassium iodide solution. For this indicator, a stream of ozone enriched oxygen is bubbled through a mixture of the reactants.

The gas that bubbles out is channelled through a solution of potassium iodide.

Once the reaction is complete and there is no more alkene left to react with the ozone, the gas goes on to oxidize potassium iodide to iodine. The reaction of potassium iodide with ozone to give iodine is indicated by the distinct violet colour of iodine.

Once the ozone is added to the reaction mixture, a reagent must be added to convert the ozonide to the required carbonyl derivative. For this conversion, 2 techniques can be employed:

  • Reductive Workup
  • Oxidative Workup

However, reductive workup conditions seen a lot more in use when compared to oxidative workup conditions. In these workup conditions, triphenylphosphine, thiourea, zinc dust, and dimethyl sulfide can be used to produce aldehydes or ketones.

On the other hand, hydrogen peroxide can be used to produce carboxylic acids. Ozone can also be employed to oxidize other functional groups such as benzyl ethers.

Pyridine is also used to buffer the reaction since small amounts of acid may be generated at the time of reaction.

A 1:1 ratio of solvent with dichloromethane co-solvent facilitates the timely cleavage of the ozonide. Ozonolysis of oleic acid is used to produce azelaic acid and pelargonic acid on an industrial scale.

Ozonolysis of Alkenes Mechanism

Step 1

The electrophilic addition of ozone to the carbon-carbon bond forms the molozonide intermediate which is quite unstable. Due to this unstable nature, the molozonide continues reacting – breaking apart to form a carbonyl molecule and a carbonyl oxide molecule as shown below:

Ozonolysis refers to the organic chemical reaction where ozone is employed to cleave the unsaturated bonds of alkenes, alkynes, and azo compounds (compounds with the functional diazenyl functional group). It is an organic redox reaction.

Step 2

The carbonyl molecule and the carbonyl oxide molecule formed in step 1 rearrange themselves, reforming to create a more stable ozonide intermediate.

This ozonide intermediate can be subjected to either an oxidative workup or a reductive workup.

The oxidative workup will give carboxylic acid as the product whereas the reductive workup will yield aldehydes or ketones.

The formation of the ozonide intermediate is illustrated below.

Ozonolysis refers to the organic chemical reaction where ozone is employed to cleave the unsaturated bonds of alkenes, alkynes, and azo compounds (compounds with the functional diazenyl functional group). It is an organic redox reaction.

Oxidative Workup

When oxidant hydrogen peroxide is used instead of zinc or dimethyl sulfide to treat the ozonide, the aldehydes formed are oxidized to carboxylic acids. Potassium Permanganate in the presence of hot acid can also be used in the oxidative workup.

Ozonolysis refers to the organic chemical reaction where ozone is employed to cleave the unsaturated bonds of alkenes, alkynes, and azo compounds (compounds with the functional diazenyl functional group). It is an organic redox reaction.

Reductive Workup

Here, the ozonide is treated with mild reducing agents such as dimethyl sulfide and zinc metal with water. The ozonide is reduced as shown below.

Ozonolysis refers to the organic chemical reaction where ozone is employed to cleave the unsaturated bonds of alkenes, alkynes, and azo compounds (compounds with the functional diazenyl functional group). It is an organic redox reaction.

Ozonolysis of Alkynes

Alkynes undergo ozonolysis to give an acid anhydride or a diketone as the final product. The fragmentation is not complete in this reaction (alkenes undergo complete fragmentation). No reducing agents are required as a simple aqueous workup is followed. If the reaction happens in the presence of water, the acid anhydride undergoes hydrolyzation to give two carboxylic acids. Ozonolysis can also be used to determine the position of the triple bond in an unknown alkyne. A few examples of alkyne ozonolysis are provided below:

Ozonolysis refers to the organic chemical reaction where ozone is employed to cleave the unsaturated bonds of alkenes, alkynes, and azo compounds (compounds with the functional diazenyl functional group). It is an organic redox reaction.

Ozonolysis of Alkynes Mechanism

The alkyne reacts with the ozone, causing the breakage of the alkyne. This gives rise to the ozonide intermediate. A simple aqueous workup follows with the help of zinc metal, finally yielding a dicarbonyl compound. The reaction can be written as:

Ozonolysis refers to the organic chemical reaction where ozone is employed to cleave the unsaturated bonds of alkenes, alkynes, and azo compounds (compounds with the functional diazenyl functional group). It is an organic redox reaction.

Ozonolysis of Elastomers – Ozone Cracking

The attack of ozone (present in trace amounts in the atmosphere) on the elastomer creates cracks. The double bond in the rubber chain is attacked by the ozone here. If the rubber product is under tension, ozone cracks begin to form. The cracks can appear around the circumference of a bent rubber tube since they are oriented at right angles to the axis of strain. These cracks are extremely dangerous when they occur in fuel pipes, growing inward from the exposed exterior surface. This can even lead to fuel leakage and fires.

Thus, ozone can be employed to cleave unsaturated bonds in alkenes, alkynes, and azo compounds. This cleaving is used in the organic chemical reaction called ozonolysis.

Frequently Asked Questions – FAQs

Q1

What is ozonolysis?

Ozonolysis refers to the organic chemical reaction where ozone is employed to cleave the unsaturated bonds of alkenes, alkynes, and azo compounds. It is an organic redox reaction.

Q2

What does oxidation of alkenes by ozone give?

The oxidation of alkenes by ozone gives alcohols, aldehydes, ketones, or carboxylic acids as a product.

Q3

What does oxidation of alkynes by ozone give?

The oxidation of alkynes by ozone gives acid anhydrides or diketones. If water is present in the reaction, the acid anhydride undergoes hydrolysis to yield two carboxylic acids.

Q4

What is the parent hydrocarbon if a compound on ozonolysis gives ethanal and methanal as the major product?

Prop-1-ene gives ethanal and methanal as the major product on ozonolysis.

Q5

What is the mechanism of ozonolysis reaction?

Ozonolysis reactions take place in two steps: Initially ozone attacks alkene molecules to form ozonide and then hydrolysis takes place leading to bond cleavage.

Er. Neeraj K.Anand is a freelance mentor and writer who specializes in Engineering & Science subjects. Neeraj Anand received a B.Tech degree in Electronics and Communication Engineering from N.I.T Warangal & M.Tech Post Graduation from IETE, New Delhi. He has over 30 years of teaching experience and serves as the Head of Department of ANAND CLASSES. He concentrated all his energy and experiences in academics and subsequently grew up as one of the best mentors in the country for students aspiring for success in competitive examinations. In parallel, he started a Technical Publication "ANAND TECHNICAL PUBLISHERS" in 2002 and Educational Newspaper "NATIONAL EDUCATION NEWS" in 2014 at Jalandhar. Now he is a Director of leading publication "ANAND TECHNICAL PUBLISHERS", "ANAND CLASSES" and "NATIONAL EDUCATION NEWS". He has published more than hundred books in the field of Physics, Mathematics, Computers and Information Technology. Besides this he has written many books to help students prepare for IIT-JEE and AIPMT entrance exams. He is an executive member of the IEEE (Institute of Electrical & Electronics Engineers. USA) and honorary member of many Indian scientific societies such as Institution of Electronics & Telecommunication Engineers, Aeronautical Society of India, Bioinformatics Institute of India, Institution of Engineers. He has got award from American Biographical Institute Board of International Research in the year 2005.

CBSE Class 11 Chemistry Syllabus

CBSE Class 11 Chemistry Syllabus is a vast which needs a clear understanding of the concepts and topics. Knowing CBSE Class 11 Chemistry syllabus helps students to understand the course structure of Chemistry.

Unit-wise CBSE Class 11 Syllabus for Chemistry

Below is a list of detailed information on each unit for Class 11 Students.

UNIT I – Some Basic Concepts of Chemistry

General Introduction: Importance and scope of Chemistry.

Nature of matter, laws of chemical combination, Dalton’s atomic theory: concept of elements,
atoms and molecules.

Atomic and molecular masses, mole concept and molar mass, percentage composition, empirical and molecular formula, chemical reactions, stoichiometry and calculations based on stoichiometry.

UNIT II – Structure of Atom

Discovery of Electron, Proton and Neutron, atomic number, isotopes and isobars. Thomson’s model and its limitations. Rutherford’s model and its limitations, Bohr’s model and its limitations, concept of shells and subshells, dual nature of matter and light, de Broglie’s relationship, Heisenberg uncertainty principle, concept of orbitals, quantum numbers, shapes of s, p and d orbitals, rules for filling electrons in orbitals – Aufbau principle, Pauli’s exclusion principle and Hund’s rule, electronic configuration of atoms, stability of half-filled and completely filled orbitals.

UNIT III – Classification of Elements and Periodicity in Properties

Significance of classification, brief history of the development of periodic table, modern periodic law and the present form of periodic table, periodic trends in properties of elements -atomic radii, ionic radii, inert gas radii, Ionization enthalpy, electron gain enthalpy, electronegativity, valency. Nomenclature of elements with atomic number greater than 100.

UNIT IV – Chemical Bonding and Molecular Structure

Valence electrons, ionic bond, covalent bond, bond parameters, Lewis structure, polar character of covalent bond, covalent character of ionic bond, valence bond theory, resonance, geometry of covalent molecules, VSEPR theory, concept of hybridization, involving s, p and d orbitals and shapes of some simple molecules, molecular orbital theory of homonuclear diatomic molecules(qualitative idea only), Hydrogen bond.

UNIT V – Chemical Thermodynamics

Concepts of System and types of systems, surroundings, work, heat, energy, extensive and intensive properties, state functions. First law of thermodynamics – internal energy and enthalpy, measurement of U and H, Hess’s law of constant heat summation, enthalpy of bond dissociation, combustion, formation, atomization, sublimation, phase transition, ionization, solution and dilution. Second law of Thermodynamics (brief introduction)
Introduction of entropy as a state function, Gibb’s energy change for spontaneous and nonspontaneous processes.
Third law of thermodynamics (brief introduction).

UNIT VI – Equilibrium

Equilibrium in physical and chemical processes, dynamic nature of equilibrium, law of mass action, equilibrium constant, factors affecting equilibrium – Le Chatelier’s principle, ionic equilibrium- ionization of acids and bases, strong and weak electrolytes, degree of ionization,
ionization of poly basic acids, acid strength, concept of pH, hydrolysis of salts (elementary idea), buffer solution, Henderson Equation, solubility product, common ion effect (with illustrative examples).

UNIT VII – Redox Reactions

Concept of oxidation and reduction, redox reactions, oxidation number, balancing redox reactions, in terms of loss and gain of electrons and change in oxidation number, applications of redox reactions.

UNIT VIII – Organic Chemistry: Some basic Principles and Techniques

General introduction, classification and IUPAC nomenclature of organic compounds. Electronic displacements in a covalent bond: inductive effect, electromeric effect, resonance and hyper conjugation. Homolytic and heterolytic fission of a covalent bond: free radicals, carbocations, carbanions, electrophiles and nucleophiles, types of organic reactions.

UNIT IX – Hydrocarbons

Classification of Hydrocarbons
Aliphatic Hydrocarbons:
Alkanes – Nomenclature, isomerism, conformation (ethane only), physical properties, chemical reactions.
Alkenes – Nomenclature, structure of double bond (ethene), geometrical isomerism, physical properties, methods of preparation, chemical reactions: addition of hydrogen, halogen, water, hydrogen halides (Markovnikov’s addition and peroxide effect), ozonolysis, oxidation, mechanism of electrophilic addition.
Alkynes – Nomenclature, structure of triple bond (ethyne), physical properties, methods of preparation, chemical reactions: acidic character of alkynes, addition reaction of – hydrogen, halogens, hydrogen halides and water.

Aromatic Hydrocarbons:

Introduction, IUPAC nomenclature, benzene: resonance, aromaticity, chemical properties: mechanism of electrophilic substitution. Nitration, sulphonation, halogenation, Friedel Craft’s alkylation and acylation, directive influence of functional group in monosubstituted benzene. Carcinogenicity and toxicity.

To know the CBSE Syllabus for all the classes from 1 to 12, visit the Syllabus page of CBSE. Meanwhile, to get the Practical Syllabus of Class 11 Chemistry, read on to find out more about the syllabus and related information in this page.

CBSE Class 11 Chemistry Practical Syllabus with Marking Scheme

In Chemistry subject, practical also plays a vital role in improving their academic scores in the subject. The overall weightage of Chemistry practical mentioned in the CBSE Class 11 Chemistry syllabus is 30 marks. So, students must try their best to score well in practicals along with theory. It will help in increasing their overall academic score.

CBSE Class 11 Chemistry Practical Syllabus

The experiments will be conducted under the supervision of subject teacher. CBSE Chemistry Practicals is for 30 marks. This contribute to the overall practical marks for the subject.

The table below consists of evaluation scheme of practical exams.

Evaluation SchemeMarks
Volumetric Analysis08
Salt Analysis08
Content Based Experiment06
Project Work04
Class record and viva04
Total30

CBSE Syllabus for Class 11 Chemistry Practical

Micro-chemical methods are available for several of the practical experiments. Wherever possible such techniques should be used.

A. Basic Laboratory Techniques
1. Cutting glass tube and glass rod
2. Bending a glass tube
3. Drawing out a glass jet
4. Boring a cork

B. Characterization and Purification of Chemical Substances
1. Determination of melting point of an organic compound.
2. Determination of boiling point of an organic compound.
3. Crystallization of impure sample of any one of the following: Alum, Copper Sulphate, Benzoic Acid.

C. Experiments based on pH

1. Any one of the following experiments:

  • Determination of pH of some solutions obtained from fruit juices, solution of known and varied concentrations of acids, bases and salts using pH paper or universal indicator.
  • Comparing the pH of solutions of strong and weak acids of same concentration.
  • Study the pH change in the titration of a strong base using universal indicator.

2. Study the pH change by common-ion in case of weak acids and weak bases.

D. Chemical Equilibrium
One of the following experiments:

1. Study the shift in equilibrium between ferric ions and thiocyanate ions by increasing/decreasing the concentration of either of the ions.
2. Study the shift in equilibrium between [Co(H2O)6] 2+ and chloride ions by changing the concentration of either of the ions.

E. Quantitative Estimation
i. Using a mechanical balance/electronic balance.
ii. Preparation of standard solution of Oxalic acid.
iii. Determination of strength of a given solution of Sodium hydroxide by titrating it against standard solution of Oxalic acid.
iv. Preparation of standard solution of Sodium carbonate.
v. Determination of strength of a given solution of hydrochloric acid by titrating it against standard Sodium Carbonatesolution.

F. Qualitative Analysis
1) Determination of one anion and one cation in a given salt
Cations‐ Pb2+, Cu2+, As3+, Al3+, Fe3+, Mn2+, Ni2+, Zn2+, Co2+, Ca2+, Sr2+, Ba2+, Mg2+, NH4 +
Anions – (CO3)2‐ , S2‐, NO2 , SO32‐, SO2‐ , NO , Cl , Br, I‐, PO43‐ , C2O2‐ ,CH3COO
(Note: Insoluble salts excluded)

2) Detection of ‐ Nitrogen, Sulphur, Chlorine in organic compounds.

G) PROJECTS
Scientific investigations involving laboratory testing and collecting information from other sources.

A few suggested projects are as follows:

  • Checking the bacterial contamination in drinking water by testing sulphide ion
  • Study of the methods of purification of water.
  • Testing the hardness, presence of Iron, Fluoride, Chloride, etc., depending upon the regional
    variation in drinking water and study of causes of presence of these ions above permissible
    limit (if any).
  • Investigation of the foaming capacity of different washing soaps and the effect of addition of
    Sodium carbonate on it.
  • Study the acidity of different samples of tea leaves.
  • Determination of the rate of evaporation of different liquids Study the effect of acids and
    bases on the tensile strength of fibres.
  • Study of acidity of fruit and vegetable juices.

Note: Any other investigatory project, which involves about 10 periods of work, can be chosen with the approval of the teacher.

Practical Examination for Visually Impaired Students of Class 11

Below is a list of practicals for the visually impaired students.

A. List of apparatus for identification for assessment in practicals (All experiments)
Beaker, tripod stand, wire gauze, glass rod, funnel, filter paper, Bunsen burner, test tube, test tube stand,
dropper, test tube holder, ignition tube, china dish, tongs, standard flask, pipette, burette, conical flask, clamp
stand, dropper, wash bottle
• Odour detection in qualitative analysis
• Procedure/Setup of the apparatus

B. List of Experiments A. Characterization and Purification of Chemical Substances
1. Crystallization of an impure sample of any one of the following: copper sulphate, benzoic acid
B. Experiments based on pH
1. Determination of pH of some solutions obtained from fruit juices, solutions of known and varied
concentrations of acids, bases and salts using pH paper
2. Comparing the pH of solutions of strong and weak acids of same concentration.

C. Chemical Equilibrium
1. Study the shift in equilibrium between ferric ions and thiocyanate ions by increasing/decreasing
the concentration of eitherions.
2. Study the shift in equilibrium between [Co(H2O)6]2+ and chloride ions by changing the
concentration of either of the ions.

D. Quantitative estimation
1. Preparation of standard solution of oxalic acid.
2. Determination of molarity of a given solution of sodium hydroxide by titrating it against standard
solution of oxalic acid.

E. Qualitative Analysis
1. Determination of one anion and one cation in a given salt
2. Cations – NH+4
Anions – (CO3)2-, S2-, (SO3)2-, Cl-, CH3COO-
(Note: insoluble salts excluded)
3. Detection of Nitrogen in the given organic compound.
4. Detection of Halogen in the given organic compound.

Note: The above practicals may be carried out in an experiential manner rather than recording observations.

We hope students must have found this information on CBSE Syllabus useful for their studying Chemistry. Learn Maths & Science in interactive and fun loving ways with ANAND CLASSES (A School Of Competitions) App/Tablet.

Frequently Asked Questions on CBSE Class 11 Chemistry Syllabus

Q1

How many units are in the CBSE Class 11 Chemistry Syllabus?

There are 9 units in the CBSE Class 11 Chemistry Syllabus. Students can access various study materials for the chapters mentioned in this article for free at ANAND CLASSES (A School Of Competitions).

Q2

What is the total marks for practicals examination as per the CBSE Class 11 Chemistry Syllabus?

The total marks for the practicals as per the CBSE Class 11 Chemistry Syllabus is 30. It includes volumetric analysis, content-based experiment, salt analysis, class record, project work and viva.

Q3

Which chapter carries more weightage as per the CBSE Syllabus for Class 11 Chemistry?

The organic chemistry chapter carries more weightage as per the CBSE Syllabus for Class 11 Chemistry.