DP Unit 10 & 20. Organic Chemistry
DP Unit 10 & 20. Organic Chemistry
DP Unit 10 & 20. Organic Chemistry
ORGANIC CHEMISTRY
Sekolah Victory Plus Regine Alfonso Balagtas, BSCT ., Dea Sukrisna, S.Pd .
Summary
Course Part
Organic Chemistry
Description
Organic chemistry is the study of carbon-containing compounds. It is called ‘organic’ because it used to be thought that carbon
compounds only came from living things, but now we know that is not true. In this topic we will learn about a wide range of types
of organic compounds, learning how to name them and some of the reactions they undergo. We will also look at the mechanisms
for some of these reactions. At HL, there is a particular focus on the fine details of isomerism, and the importance of the shape
of molecules.
Essential Understandings
Today, we may be starting to experience the consequences of using fossil fuels as our main source of energy. There is a vast
range of
products that can be derived from fossil fuels as a result of carbon’s rich chemistry. This raises the question “are they too
valuable to
burn?”
Inquiry Questions
Content-based What are the main classes of organic chemicals, their structures and uses?
Content-based How can we convert one organic chemical to another using reaction pathways?
Skills-based Can you demonstrate your practical skills in using reaction pathways to make and purifying
organic compounds?
Debatable Should we reserve crude oil solely for the purpose of obtaining raw materials, especially now that
it is getting to be in short supply world-wide?
Transfer goals
• Structure, bonding and chemical reactions involving functional group inter-conversions are key strands in organic
chemistry.
Missed concepts/misunderstandings
Students tend to get mixed up with names of classes of organic chemicals and functional groups. They also struggle with
memorising
Curriculum
Aims
Appreciate scientific study and creativity within a global context through stimulating and challenging opportunities
Acquire a body of knowledge, methods and techniques that characterize science and technology
Become critically aware, as global citizens, of the ethical implications of using science and technology
Objectives
Apply
Syllabus Content
Core
Nature of science:
Ethical implications - drugs, additives and pesticides can have harmful effects on both people and the
environment.
Understandings:
A homologous series is a series of compounds of the same family, with the same general formula, which differ
from each other by a common structural unit.
Structural isomers are compounds with the same molecular formula but different arrangements of atoms.
Saturated compounds contain single bonds only and unsaturated compounds contain double or triple bonds.
Identification of different classes: alkanes, alkenes, alkynes, halogenoalkanes, alcohols, ethers, aldehydes,
ketones, esters, carboxylic acids, amines, amides, nitriles and arenes.
Identification of typical functional groups in molecules eg phenyl, hydroxyl, carbonyl, carboxyl, carboxamide,
aldehyde, ester, ether, amine, nitrile, alkyl, alkenyl and alkynyl.
Identification of primary, secondary and tertiary carbon atoms in halogenoalkanes and alcohols and primary,
secondary and tertiary nitrogen atoms in amines.
Nature of science:
Use of data - much of the progress that has been made to date in the developments and applications of scientific
research can be mapped back to key organic chemical reactions involving functional group interconversions.
Understandings:
Alkanes: Alkanes have low reactivity and undergo free-radical substitution reactions.
Alkenes: Alkenes are more reactive than alkanes and undergo addition reactions. Bromine water can be used to
distinguish between alkenes and alkanes.
Alcohols: Alcohols undergo nucleophilic substitution reactions with acids (also called esterification or
condensation) and some undergo oxidation reactions.
Halogenoalkanes: Halogenoalkanes are more reactive than alkanes. They can undergo (nucleophilic) substitution
reactions. A nucleophile is an electron-rich species containing a lone pair that it donates to an electron-deficient
carbon.
Polymers: Addition polymers consist of a wide range of monomers and form the basis of the plastics industry.
Benzene: Benzene does not readily undergo addition reactions but does undergo electrophilic substitution
reactions.
Alkanes: Writing equations for the complete and incomplete combustion of hydrocarbons. Explanation of the
reaction of methane and ethane with halogens in terms of a free-radical substitution mechanism involving
photochemical homolytic fission.
Alkenes: Writing equations for the reactions of alkenes with hydrogen and halogens and of symmetrical alkenes
with hydrogen halides and water. Outline of the addition polymerization of alkenes. Relationship between the
structure of the monomer to the polymer and repeating unit.
Alcohols: Writing equations for the complete combustion of alcohols. Writing equations for the oxidation reactions
of primary and secondary alcohols (using acidified potassium dichromate(VI) or potassium manganate(VII) as
oxidizing agents). Explanation of distillation and reflux in the isolation of the aldehyde and carboxylic acid
products. Writing the equation for the condensation reaction of an alcohol with a carboxylic acid, in the presence
of a catalyst (eg concentrated sulfuric acid) to form an ester.
Halogenoalkanes: Writing the equation for the substitution reactions of halogenoalkanes with aqueous sodium
hydroxide.
Nature of science:
Looking for trends and discrepancies - by understanding different types of organic reactions and their
mechanisms, it is possible to synthesize new compounds with novel properties which can then be used in several
applications. Organic reaction types fall into a number of different categories.
Collaboration and ethical implications - scientists have collaborated to work on investigating the synthesis of new
pathways and have considered the ethical and environmental implications of adopting green chemistry.
Understandings:
Nucleophilic Substitution Reactions: SN1 represents a nucleophilic unimolecular substitution reaction and SN2
represents a nucleophilic bimolecular substitution reaction. SN1 involves a carbocation intermediate. SN2
involves a concerted reaction with a transition state. For tertiary halogenoalkanes the predominant mechanism
is SN1 and for primary halogenoalkanes it is SN2. Both mechanisms occur for secondary halogenoalkanes. The
rate determining step (slow step) in an SN1 reaction depends only on the concentration of the halogenoalkane,
rate = k[halogenoalkane]. For SN2, rate = k[halogenoalkane][nucleophile]. SN2 is stereospecific with an inversion
of configuration at the carbon.
SN2 reactions are best conducted using aprotic, non-polar solvents and SN1 reactions are best conducted using
protic, polar solvents.
Electrophilic Addition Reactions: An electrophile is an electron-deficient species that can accept electron pairs
from a nucleophile. Electrophiles are Lewis acids. Markovnikov’s rule can be applied to predict the major
product in electrophilic addition reactions of unsymmetrical alkenes with hydrogen halides and interhalogens. The
formation of the major product can be explained in terms of the relative stability of possible carbocations in the
reaction mechanism.
Electrophilic Substitution Reactions: Benzene is the simplest aromatic hydrocarbon compound (or arene) and has
a delocalized structure of π bonds around its ring. Each carbon to carbon bond has a bond order of 1.5. Benzene
is susceptible to attack by electrophiles.
Reduction Reactions: Carboxylic acids can be reduced to primary alcohols (via the aldehyde). Ketones can be
reduced to secondary alcohols. Typical reducing agents are lithium aluminium hydride (used to reduce carboxylic
acids) and sodium borohydride.
Nucleophilic Substitution Reactions: Explanation of why hydroxide is a better nucleophile than water. Deduction
of the mechanism of the nucleophilic substitution reactions of halogenoalkanes with aqueous sodium hydroxide
in terms of SN1 and SN2 mechanisms. Explanation of how the rate depends on the identity of the halogen (ie the
leaving group), whether the halogenoalkane is primary, secondary or tertiary and the choice of solvent.
Electrophilic Addition Reactions: Deduction of the mechanism of the electrophilic addition reactions of alkenes
with halogens/interhalogens and hydrogen halides.
Electrophilic Substitution Reactions: Deduction of the mechanism of the nitration (electrophilic substitution)
reaction of benzene (using a mixture of concentrated nitric acid and sulfuric acid).
Reduction Reactions: Writing reduction reactions of carbonyl containing compounds: aldehydes and ketones to
primary and secondary alcohols and carboxylic acids to aldehydes, using suitable reducing agents. Conversion
of nitrobenzene to phenylamine via a two-stage reaction.
Nature of science:
Scientific method - in synthetic design, the thinking process of the organic chemist is one which invokes retro-
synthesis and the ability to think in a reverse-like manner.
Understandings:
The synthesis of an organic compound stems from a readily available starting material via a series of discrete
steps. Functional group interconversions are the basis of such synthetic routes.
Deduction of multi-step synthetic routes given starting reagents and the product(s).
20.3 Stereoisomerism
Nature of science:
Transdisciplinary - the three-dimensional shape of an organic molecule is the foundation pillar of its structure and
Understandings:
Stereoisomers are subdivided into two classes—conformational isomers, which interconvert by rotation about a
σ bond and configurational isomers that interconvert only by breaking and reforming a bond.
Configurational isomers are further subdivided into cis-trans and E/Z isomers and optical isomers.
Cis-trans isomers can occur in alkenes or cycloalkanes (or heteroanalogues) and differ in the positions of
atoms (or groups) relative to a reference plane. According to IUPAC, E/Z isomers refer to alkenes of the form
R1R2C=CR3R4 (R1 ≠ R2, R3 ≠ R4) where neither R1 nor R2 need be different from R3 or R4.
An optically active compound can rotate the plane of polarized light as it passes through a solution of the
compound. Optical isomers are enantiomers. Enantiomers are non-superimposeable mirror images of each other.
Diastereomers are not mirror images of each other.
A racemic mixture (or racemate) is a mixture of two enantiomers in equal amounts and is optically inactive.
Content
Skills
• Explanation of the trends in boiling points of members of a homologous series.
• Distinction between empirical, molecular, and structural formulas.
• Identification of different classes: alkanes, alkenes, alkynes, halogenoalkanes, alcohols, ethers, aldehydes, ketones, esters,
carboxylic acids, amines, amides, nitriles, and arenes.
• Identification of typical functional groups in molecules eg phenyl, hydroxyl, carbonyl, carboxyl, carboxamide, aldehyde,
ester, ether, amine, nitrile, alkyl, alkenyl, and alkynyl.
• Construction of 3-D models (real or virtual) of organic molecules.
• Application of IUPAC rules in the nomenclature of straight-chain and branched-chain isomers.
• Identification of primary, secondary, and tertiary carbon atoms in halogenoalkanes and alcohols and primary, secondary, and
Alkanes:
Alkenes:
• Writing equations for the reactions of alkenes with hydrogen and halogens and of symmetrical alkenes with hydrogen
halides and water.
• Outline of the addition polymerization of alkenes.
• Describe the relationship between the structure of the monomer to the polymer and repeating unit.
Alcohols:
Halogenoalkanes:
• Writing the equation for the substitution reactions of halogenoalkanes with aqueous sodium hydroxide.
(HL ONLY)
• Deduction of the mechanism of the electrophilic addition reactions of alkenes with halogens/interhalogens and hydrogen
halides.
Reduction Reactions:
• Writing reduction reactions of carbonyl-containing compounds: aldehydes and ketones to primary and secondary alcohols and
carboxylic acids to aldehydes, using suitable reducing agents.
• Deduction of multi-step synthetic routes given starting reagents and the product(s).
• Construction of 3-D models (real or virtual) of a wide range of stereoisomers.
• Explanation of stereoisomerism in non-cyclic alkenes and C3 and C4cycloalkanes.
• Comparison between the physical and chemical properties of enantiomers.
• Description and explanation of optical isomers in simple organic molecules.
Concepts
• "A homologous series is a series of compounds of the same family, with the same general formula, which differ from each
other by a common structural unit."
• "Structural formulas can be represented in full and condensed format."
• "Structural isomers are compounds with the same molecular formula but different arrangements of atoms."
• "Functional groups are the reactive parts of molecules."
• "Saturated compounds contain single bonds only and unsaturated compounds contain double or triple bonds."
• "Benzene is an aromatic, unsaturated hydrocarbon."
Alkanes:
Alkenes:
• "Alkenes are more reactive than alkanes and undergo addition reactions. Bromine water can be used to distinguish between
alkenes and alkanes."
Alcohols:
• "Alcohols undergo nucleophilic substitution reactions with acids (also called esterification or condensation) and some
undergo oxidation reactions."
Halogenoalkanes:
• "Halogenoalkanes are more reactive than alkanes. They can undergo (nucleophilic) substitution reactions. A nucleophile is
an electron-rich species containing a lone pair that it donates to an electron-deficient carbon."
Polymers:
• "Addition polymers consist of a wide range of monomers and form the basis of the plastics industry."
Benzene:
• "Benzene does not readily undergo addition reactions but does undergo electrophilic substitution reactions."
(HL ONLY)
• "SN1 represents a nucleophilic unimolecular substitution reaction and SN2 represents a nucleophilic bimolecular
substitution reaction. SN1 involves a carbocation intermediate. SN2 involves a concerted reaction with a transition state."
• "For tertiary halogenoalkanes the predominant mechanism is SN1 and for primary halogenoalkanes it is SN2. Both
mechanisms occur for secondary halogenoalkanes."
• "The rate determining step (slow step) in an SN1 reaction depends only on the concentration of the halogenoalkane, rate =
k[halogenoalkane]. For SN2, rate = k[halogenoalkane][nucleophile]. SN2 is stereospecific with an inversion of configuration
at the carbon."
• "SN2 reactions are best conducted using aprotic, non-polar solvents and SN1 reactions are best conducted using protic,
polar solvents."
• "An electrophile is an electron-deficient species that can accept electron pairs from a nucleophile. Electrophiles are Lewis
acids."
• "Markovnikov's rule can be applied to predict the major product in electrophilic addition reactions of unsymmetrical alkenes
with hydrogen halides and interhalogens. The formation of the major product can be explained in terms of the relative
stability of possible carbocations in the reaction mechanism."
• "Benzene is the simplest aromatic hydrocarbon compound (or arene) and has a delocalized structure of π bonds around its
ring. Each carbon to carbon bond has a bond order of 1.5. Benzene is susceptible to attack by electrophiles."
Reduction Reactions:
• "Carboxylic acids can be reduced to primary alcohols (via the aldehyde). Ketones can be reduced to secondary alcohols.
Typical reducing agents are lithium aluminium hydride (used to reduce carboxylic acids) and sodium borohydride."
• "The synthesis of an organic compound stems from a readily available starting material via a series of discrete steps.
Functional group interconversions are the basis of such synthetic routes."
• "Retro-synthesis of organic compounds."
• "Stereoisomers are subdivided into two classes—conformational isomers, which interconvert by rotation about a σ bond
and configurational isomers that interconvert only by breaking and reforming a bond. Configurational isomers are further
subdivided into cis-trans and E/Z isomers and optical isomers."
• "Cis-trans isomers can occur in alkenes or cycloalkanes (or heteroanalogues) and differ in the positions of atoms (or groups)
relative to a reference plane. According to IUPAC, E/Z isomers refer to alkenes of the form R1R2C=CR3R4 (R1 ≠ R2, R3 ≠
R4) where neither R1 nor R2 need be different from R3 or R4."
• "A chiral carbon is a carbon joined to four different atoms or groups."
• "An optically active compound can rotate the plane of polarized light as it passes through a solution of the compound.
Optical isomers are enantiomers. Enantiomers are non-superimposeable mirror images of each other. Diastereomers are not
mirror images of each other."
• "A racemic mixture (or racemate) is a mixture of two enantiomers in equal amounts and is optically inactive."
Assessment
Formative assessment
Summative assessment
NOV TOPIC 10 Summative PAPER 1
23 HL SL Summative Paper 1 Tuesday at 8:30 AM
Learning Experiences
• Students should
• Students should
Pedagogical approaches
Introduction to Unit
Students .
Students
Learning Objectives
10.1.2. U10: Ethical implications - drugs, additives and pesticides can have harmful effects on both people and the
environment.
Learning Objectives:
10.2.1. U10: Use of data - much of the progress that has been made to date in the developments and applications of scientific
research can be mapped back to key organic chemical reactions involving functional group interconversions.
• Describe esters
• Name esters, ethers, and amides
• Classify the types of amines
• Describe the properties of esters
• Determine the factors that affect the boiling points of organic compounds
• Differentiate homolytic and heterolytic bond fission
AHL
Learning Objectives:
19.1.1. U19: Looking for trends and discrepancies - by understanding different types of organic reactions and their
mechanisms, it is possible to synthesize new compounds with novel properties which can then be used in several applications.
Organic reaction types fall into a number of different categories.
19.1.2. U19: Collaboration and ethical implications - scientists have collaborated to work on investigating the synthesis of new
pathways and have considered the ethical and environmental implications of adopting green chemistry.
Learning Objectives:
19.2.1. U19: Scientific method - in synthetic design, the thinking process of the organic chemist is one which invokes retro-
synthesis and the ability to think in a reverse-like manner.
Topic - Stereoisomerism
Learning Objectives:
19.3.1. U19: Transdisciplinary - the three-dimensional shape of an organic molecule is the foundation pillar of its structure and
often its properties. Much of the human body is chiral.
Feedback
• for improvement of teaching
• for improvement of learning
Student expectations
• practice exercises and problem sets
• formative and summative assessments
• acceptable evidence of understanding should depend on the marking schemes
Support materials
Examples
Sample Exam Questions
Mark Schemes
Learning Process
Lecture
PowerPoint lecture/notes
Activities
Problem_Set_10.1__with_Answer_Key_.pdf
Problem_Set_10.1.pdf
Problem_Set_10.2__with_Answer_Key_.pdf
Problem_Set_10.2.pdf
_1__Functional_Groups.pdf
_2__Nomenclature_of_Alkanes__Alkenes___Alkynes.pdf
_3__Classification_of_Organic_Compounds.pdf
_4__Alcohols_and_Carboxylic_Acids_Nomenclature.pdf
_5__Aldehydes_and_Ketones_Nomenclature.pdf
_6__Addition_Reactions_of_Alkenes.pdf
_7__Addition_Polymerization.pdf
_8__Reactions_of_Alcohols.pdf
_9__Esters.pdf
_1__Markovnikov_s_Rule_with_Answers.pdf
_2__Synthetic_Routes_with_Answers.pdf
PROBLEM_SET__ANSWER_KEY_.pdf
Problem_Set_1-7.jpg
Problem_Set_8-10.jpg
Differentiation
the knowledge of chemical bonding is used to determine students readiness. When planning the learning experience,
teacher prepare a self assessment on the chemical bonding.
What did we find compelling? the students struggle with organic reaction and functional group. This is indeed because of
the weak understanding in chemical bonding. Students with stronger understanding of chemical bonding able to understand
the content easier.
Notes/changes/suggestions:
The planning went longer that it was planned due to the additional time needed to review chemical bonding
Resources
_1__Sn1_and_Sn2_Mechanism.pdf
3 MB PDF Document
_2__Markovnikov_s_Rule__Nitration_of_Benzene___Reduction_of_Carbonyl_Compounds.pdf
2 MB PDF Document
_3__Reduction_of_Nitrobenzene___Synthetic_Routes__Retro-synthesis_.pdf
2 MB PDF Document
_4__Isomerism__Intro_to_cis-trans__E-Z_.pdf
4 MB PDF Document
_5__Configurational_Isomerism.pdf
1 MB PDF Document
_6__Optical_Isomerism.pdf
2 MB PDF Document
_7__Conformational_Isomers.pdf
900 KB PDF Document
Problem_Set_10.2__with_Answer_Key_.pdf
200 KB PDF Document
Problem_Set_10.1__with_Answer_Key_.pdf
100 KB PDF Document
_9__Esters.pdf
400 KB PDF Document
_8__Reactions_of_Alcohols.pdf
400 KB PDF Document
_7__Addition_Polymerization.pdf
300 KB PDF Document
_6__Addition_Reactions_of_Alkenes.pdf
300 KB PDF Document
_5__Aldehydes_and_Ketones_Nomenclature.pdf
200 KB PDF Document
_4__Alcohols_and_Carboxylic_Acids_Nomenclature.pdf
200 KB PDF Document
_3__Classification_of_Organic_Compounds.pdf
300 KB PDF Document
_2__Nomenclature_of_Alkanes__Alkenes___Alkynes.pdf
300 KB PDF Document
_1__Functional_Groups.pdf
200 KB PDF Document
_5__Continuation_of_Organic_Reactions_and_Benzene.pdf
5 MB PDF Document
_4__Organic_Reactions___Factors_Affecting_Boiling_Points_of_Organic_Compounds.pdf
7 MB PDF Document
_3__Continuation_of_Nomenclature_and_Classification_of_Organic_Compounds.pdf
2 MB PDF Document
_2__Structural_Isomerism__Nomenclature_and_Classification_of_Organic_Compounds.pdf
8 MB PDF Document
_1__Homologous_Series__Functional_Groups___Nomenclature_of_Alkanes__Alkenes___Alkynes_.pdf
8 MB PDF Document