Carbon is the basis not only of the structure of living tissues but is also found in fuels, foods, medicines, polymers and many other materials that we use in everyday life. In this unit students investigate the structures and reactions of carbon-based organic compounds, including considering how green chemistry principles are applied in the production of synthetic organic compounds. They study the metabolism of food and the action of medicines in the body. They explore how laboratory analysis and various instrumentation techniques can be applied to analyse organic compounds in order to identify them and to ensure product purity.
Students conduct practical investigations related to the synthesis and analysis of organic compounds, involving reaction pathways, organic synthesis, identification of functional groups, direct redox titrations, solvent extraction and distillations.
Throughout the unit students use chemistry terminology including symbols, formulas, chemical nomenclature and equations to represent and explain observations and data from their own investigations and to evaluate the chemistry-based claims of others.
A student-designed scientific investigation involving the generation of primary data related to the production of energy and/or chemicals and/or the analysis or synthesis of organic compounds is undertaken in either Unit 3 or Unit 4, or across both Units 3 and 4, and is assessed in Unit 4 Outcome 3. The design, analysis and findings of the investigation are presented in a scientific poster format as outlined on pages 14 and 15.

Structure, nomenclature and properties of organic compounds

• characteristics of the carbon atom that contribute to the diversity of organic compounds formed, with reference to valence electron number, relative bond strength, relative stability of carbon bonds with other elements, degree of unsaturation, and the formation of structural isomers
• molecular, structural and semi-structural (condensed) formulae and Skeletal structures of alkanes (including cyclohexane), alkenes, benzene, haloalkanes, primary amines, primary amides, alcohols (primary, secondary and tertiary), aldehydes, ketones, carboxylic acids and non-branched esters
• the International Union of Pure and Applied Chemistry (IUPAC) systematic naming of organic compounds up to C8, with no more than two functional groups for a molecule, limited to non-cyclic hydrocarbons, haloalkanes, primary amines, primary amides, alcohols (primary, secondary and tertiary), aldehydes, ketones, carboxylic acids and non-branched esters
• trends in physical properties within homologous series (boiling point and melting point, viscosity), with reference to structure and bonding
  
  Lesson 1 Solutions - simple naming of hydrocarbons
  Lesson 1a Solutions - simple naming of hydrocarbons with functional groups
  Lesson 1b Solutions - writing condensed (semi-structurall) formulae Video worksheet
  Lesson 2 Solutions - naming hydrocarbons with more than one functional group
  Lesson 2a - Video worksheet- naming compounds with two functional groups
  Lesson 3 Solutions - esters
  Lesson 5 Solutions -identifying chiral molecules Video worksheet
  Lesson 6 Solutions - trends of organic molecules
  Lesson 6a -trends of organic molecules due to branching
  
  Reactions of organic compounds

• organic reactions and pathways , including equations, reactants, products, reaction conditions and catalysts (specific enzymes not required):
  - synthesis of primary haloalkanes and primary alcohols by substitution
  - addition reactions of alkenes
  - the esterification between an alcohol and a carboxylic acid
  - hydrolysis of esters
  - pathways for the synthesis of primary amines and carboxylic acids
  - transesterification of plant triglycerides using alcohols to produce biodiesel
  
• calculations of percentage yield and atom economy of single-step or overall reaction pathways, and the advantages for society and for industry of developing chemical processes with a high atom economy
• the sustainability of the production of chemicals, with reference to the green chemistry principles of use of renewable feedstocks, catalysis and designing safer chemicals

Lesson 7 Solutions Oxidation of primary and secondary alcohols
Lesson 7a -  Reaction pathways summary sheet
Video worksheet 1, video worksheet 2, video worksheet 3, video worksheet 4.
Lesson 8 solutions- Atom economy and percentage yield
Video worksheet - Atom economy and percentage yield.
Lesson 9 Solutions - reactions of alkenes, alkanes and haloalkanes.
Lesson 10 Solutions - reactions of alcohols, amines, carboxylic acids and esters.
Lesson 10a - Video worksheet using reactions with organic molecules in polymerisation reactions.

Isomers
stereoisomers
optical isomers
cis and trans isomers.

Ethene and addition reactions
Naming organic compounds
-with more than one functional group.
Homologous
Substitution reactions
Esters
Naming esters
Addition reactions
Condensation reactions
Condensation polymerisation

Oxidation of primary and secondary alcohols

Formulae, structural and semistructural

Naming organic compounds
Quiz 1 Solutions
Quiz 2 Solutions

Organic Reaction Pathways

Quiz 1 Solutions
Quiz 2 Solutions
Quiz 3 Solutions
Quiz 4 Solutions
Quiz 5 Solutions
Quiz 6 Solutions
Quiz 7 Solutions - percentage atom economy, pathways, chirality and naming.
Quiz 8 Solutions - Naming, pathways
Quiz 9 Solutions - Naming, pathways, stereoisomers
Quiz 10 Solutions -Naming, isomers, atom economy and percentage yield, chirality, trends.
Quiz 11 Solutions -Naming,pathways, polymerisation
Quiz 12 Solutions -Naming,pathways, stoichiometry.

Quiz 13 Video - -Naming,pathways, analytical chemistry (h-nmr, c-nmr, HPLC)

Reaction pathways and functional groups summary sheet

Activity-making esters

Organic past exam questions

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Activity-making biodiesel

• hydrolytic reactions of proteins, carbohydrates and fats and oils to break down large biomolecules in food to produce smaller molecules
  
  
• condensation reactions to synthesise large biologically important molecules for storage as proteins, starch, glycogen and lipids (fats and oils)

Lesson 1 Solutions- amino acids and proteins
Lesson 2 Solutions- proteins

Lesson 1 Solutions - carbohydrates
Lesson 2 Solutions - artificial sweetener (aspartame)

Lesson 1 Solutions - fats and oils

Proteins
- amino acids
- zwitterions
- protein structure summary
- enzymes (biological catalysts)

Carbohydrates Polysaccharides:
- cellulose
- starch and hydrogen bonding
- glycogen

Fats and oils
-Triglycerides
- Fatty acids

Enzymes

Hydrolysis

Metabolism of macromolecules

Food and Biomacromolecules -past exam questions.
(DNA is not part of Unit 4)

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Ongoing revision task 1 Solutions - enthalpy, electroplating and naming organic compounds

Ongoing revision task 2 Solutions - equilibrium, enthalpy, organic

Ongoing revision task 3 Solutions - equilibrium, galvanic cells and
organic pathways

Ongoing revision task 4 Solutions - trends in organic molecules and electrolysis

Ongoing revision task 5 Solutions - reaction pathways, enthalpy, galvanic

Ongoing revision task 6 Solutions - galvanic cells, electrolytic cells and reaction pathways.

Ongoing revision task 7 Solutions - enthalpy, galvanic, redox reaction, isomers and atom economy.

Ongoing revision task 7a - enthalpy, equilibrium. Video

Area of Study 2
How are organic compounds analysed and used?

In this area of study students focus on laboratory and instrumental analyses of organic compounds, and the function of some organic compounds as medicines. They use distillation to separate mixtures, use volumetric analysis to calculate redox quantities, and explore how instrumental analysis is used to ensure the quality of consumer products. Students explain how some medicines that bind to the active sites of enzymes function by inhibiting the enzymes’ mode of action.

The selection of learning contexts should allow students to develop practical techniques to analyse organic compounds. Students develop their skills in the use of scientific equipment and apparatus. They may perform qualitative tests to identify features of organic compounds, such as the degree of saturation in fats and oils and the identification of functional groups in an unknown compound. Students may perform quantitative analyses including redox titrations to determine concentrations and quantities of substances, such as the amount of Vitamin C in fruits. They design and improve on experiments such as the testing of the viscosity of alcohols. They respond to challenges such as the identification of a molecule using primary data from analytical techniques used in the laboratory or secondary data obtained from spectroscopy. Students may use distillation to extract and purify the natural organic compounds in plants, such as extracting limonene from orange peel.

Outcome 2

On completion of this unit the student should be able to apply qualitative and quantitative tests to analyse organic compounds and their structural characteristics, deduce structures of organic compounds using instrumental analysis data, explain how some medicines function, and experimentally analyse how some natural medicines can be extracted and purified.

To achieve this outcome the student will draw on key knowledge outlined in Area of Study 2 and the related key science skills on pages 11 and 12 of the study design.

Laboratory analysis of organic compounds

• qualitative tests for the presence of carbon-carbon double bonds, hydroxyl and carboxyl functional groups
• applications and principles of laboratory analysis techniques in verifying components and purity of consumer products, including melting point determination and distillation (simple and fractional)
• measurement of the degree of unsaturation of compounds using iodine

• volumetric analysis, including calculations of excess and limiting reactants using redox titrations (excluding back titrations)

Lesson 1 Solutions - volumetric analysis

Lesson 1a - volumetric analysis- selecting the right indicator
Video worksheet - selecting the right indicator

Lesson 2 Solutions - titrations involving redox reactions, %m/m and errors

Lesson 3 Solutions- why dilute samples, (dilution)

Lesson 3a Solutions

Lesson 3b Solutions

Summary Sheet of volumetric analysis

Volumetric analysis starts with a discussion of acid base reaction and the use of indicators

Oxidants and reductants should also be revisited as should oxidation numbers and writing half equations.

A discussion of possible errors when using the burette and pipette is important

The following terms must be clear to students
Aliquot
Concordant results
Titre
Primary standard
Standard solution
Indicator
Strong or weak acid
Titrations
Titration curves of weak and strong acids weak and strong bases

Selection of Friday quizzes. The teacher can decide when to use these quizzes to gauge student progress.
Quiz 1 Solution

Quiz 2 Solution

Quiz 3 Solution

Quiz 4 Solution - contains back titration, not in the 2016-2023 course)

Quiz 5 Solution- contains back titration, not in the 2016-2023 course)

Quiz 6 Solutions

Quiz 7 Solutions

Quiz 8 Solutions

Quiz 9 Solutions

Revision volumetric analysis Solution

Revision volumetric analysis Solution

Revision - video worksheet (1) - contains atom economy, %yield, volumetric and spectra analysis. This video is the same as Ongoing Revision 20, below

Revision - video worksheet (2)- contains volumetric analysis

Try some worksheets on:

titration

Analysis of ammonia in household cleaner

Available chlorine in household cleaner

Volumetric analysis from past exams.
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• applications of mass spectrometry (excluding features of instrumentation and operation) and interpretation of qualitative and quantitative data, including identification of molecular ion peak, determination of molecular mass and identification of simple fragments
  Lesson 1 Solutions - mass spectroscopy
  Video worksheet mass spectroscopy and identifying molecules using mass spectrometry

Mass Spectroscopy

Quiz 1 Solution
Quiz 2 Solution
Quiz 3 Solution

Spectroscopy test

Solutions

Spectroscopy past exam questions

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• structural determination of organic compounds by low resolution carbon-13 nuclear magnetic resonance (13C-NMR) spectral analysis, using chemical shift values to deduce the number and nature of different carbon environments
• structural determination of organic compounds by low and high resolution proton nuclear magnetic resonance (1H-NMR) spectral analysis, using chemical shift values, integration curves (where the height is proportional to the area underneath a peak) and peak splitting patterns (excluding coupling constants), and application of the n+1 rule (where n is the number of neighbouring protons) to deduce the number and nature of different proton environments

Lesson 1 Solutions Introduction to HNMR, terms
Lesson 2 Solutions Introduction to NMR spectra and the n+1 rule
Video worksheet
Lesson 3 Solutions Problems involving spectra and the n+1 rule.
Lesson 4 Solutions Interpreting the spectra and deriving the molecular structure.
Lesson 4a - Exercises in identifying molecules from spectra (n + 1 rule)
Lesson 4b - Exercises in identifying molecules with nitrogen from spectra (n + 1 rule)
Lesson 4c - Video worksheet in identifying molecules using HNMR
Lesson 5 Solutions ¹³CNMR spectra

Ongoing revision task 8 Solutions - interpreting 1HNMR spectra, percentage yield, reaction pathways. Video solutions
Ongoing revision task 8a solutions - Organic pathways and naming, enthalpy, equilibrium, fuels.

¹H NMR and ¹³C NMR

Quiz 1 Solution
Quiz 2 Solution
Quiz 3 Solution
Quiz 4 Solution
Quiz 5 Solution

• identification of bond types by qualitative infrared spectroscopy (IR) data analysis using characteristic absorption bands

Lesson 1 Solutions - IR spectroscopy

Lesson 2 - Video worksheet in identifying molecules using IR

IR

Quiz 1 Solution contains IR and HNMR
Quiz 2 Solution contains IR and HNMR
Quiz 3 Solution contains IR, MS and HNMR
Quiz 4 Solution contains IR and MS
Quiz 5 Solution contains IR and ¹HNMR
Quiz 6 Solution contains IR and ¹HNMR

• deduction of the structures of simple organic compounds using a combination of mass spectrometry (MS), infrared spectroscopy (IR), proton nuclear magnetic resonance (1H-NMR) and carbon-13 nuclear magnetic resonance (13C-NMR) (limited to data analysis)
• the roles and applications of laboratory and instrumental analysis, with reference to product purity and the identification of organic compounds or functional groups in isolation or within a mixture

Lesson 1 General questions on spectroscopy - video worksheet on deriving the molecular structure.

Spectroscopy Revision task 1 Solutions
Spectroscopy Revision task 2 Solutions
Spectroscopy Revision task 3 Solutions

Revision task 1 Solutions - organic chemistry and spectroscopy

Revision exercises involving IR and NMR

Revision Video solutions - Naming, atom economy, yield, spectroscopy,NMR, HPLC, pathways.

Revision Solutions - Naming, atom economy, yield, spectroscopy,¹H NMR, pathways.

Summary of analytical techniques.

Yet another summary

the principles of chromatography, including high performance liquidchromatography (HPLC) and the use of retention times and the construction of a calibration curve to determine the concentration of an organic compound in a solution (excluding features of instrumentation and operation)

Lesson 1 Solution
Video lesson- chromatography and questions with solutions

Before commencing with chromatography it is important that students are familiar with
-ppm
-(v/v)%
-(w/v)%
-(w/w)%

Video worksheet (converting units)

Chromatography

-- High pressure liquid Chromatography
-- Gas Liquid Chromatography

Quiz 1 Solution

Quiz 2 Solution

Quiz 3 Solution

Quiz 4 Solution

Quiz 5 Solution

Quiz 6 Solution

Chromatography questions from past exams.

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Activity - TLC-plant pigments

Ongoing revision task 9 Solutions - alcohols, percentage yield, atom economy, chromatography and spectroscopy.

Ongoing revision task 10 Solutions - percentage yield, atom economy, chromatography and spectroscopy

Medicinal chemistry

• extraction and purification of natural plant compounds as possible active ingredients for medicines, using solvent extraction and distillation
  
  Lesson 1 Video worksheet - Separating techniques, solvent extraction and steam disitllation
  

• identification of the structure and functional groups of organic molecules that are medicines
• significance of isomers and the identification of chiral centres (carbon atom surrounded by four different groups) in the effectiveness of medicines
  
  Lesson 2 Video worksheet - Functional groups and stereospecificity in inetractions between drugs and biomacromolecules in the body.
  
  
• enzymes as protein-based catalysts in living systems: primary, secondary, tertiary and quaternary structures and changes in enzyme function in terms of structure and bonding as a result of increased temperature (denaturation), decreased temperature (lowered activity), or changes in pH (formation of zwitterions and denaturation)
  
• medicines that function as competitive enzyme inhibitors: organic molecules that bind through lock-and-key mechanism to an active site preventing binding of the actual substrate
  
  Lesson 3 Video worksheet - Enzyme fubnctinality and medicines as competitive and non-competitive inhibitors.

Synthesis of Aspirin

Solvent extraction of capsaicin. Solution

Ongoing revision task 11 Solutions - volumetric analysis, food chemistry

Ongoing revision task 12 Solutions - volumetric analysis, spectroscopy, food chemistry.

Ongoing revision task 13 Solutions - volumetric analysis, spectroscopy, food chemistry, chirality

Ongoing revision task 14 Solutions-proteins, enzymes, cofactors

Ongoing revision task 15 Solutions -proteins, enzymes, enthalpy, spectroscopy, HPLC, calorimetry,

Quiz 1 Solutions (includes DNA which is not part of Unit 4)

Quiz 2 Solutions (includes DNA which is not part of Unit 4)

Quiz 3 Solutions

Practical investigation

Students undertake a student-designed scientific investigation in either Unit 3 or Unit 4, or across both Units 3 and 4. The investigation involves the generation of primary data related to the production of energy and/or chemicals and/or the analysis or synthesis of organic compounds, and should be inspired by a contemporary chemical challenge or issue. The investigation draws on knowledge and related key science skills developed across Units 3 and 4 and is undertaken by students in the laboratory and/or in the field.
When undertaking the investigation students are required to apply the key science skills to develop a question, state an aim, formulate a hypothesis and plan a course of action to answer the question, while complying with safety and ethical guidelines. Students then undertake an experiment to generate primary quantitative data, analyse and evaluate the data, identify limitations of data and methods, link experimental results to scientific ideas, discuss implications of the results, and draw a conclusion in response to the question. The presentation format for the investigation is a scientific poster constructed according to the structure outlined on page 14. A logbook is maintained by students for recording, assessment and authentication purposes.

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Lesson 1 Solutions - errors, validity, reliability/repeatability, reproducibility

Experimental technique

Quiz 1 Solutions

Quiz 2 Solutions

Quiz 3 Solutions

Experimental technique (ET)

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Application of chemical knowledge

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Revision task 1 Solutions Q1 atomic absorption is no longer on the course. It contains questions on spectroscopy and organic chemistry.
Revision task 2 Solutions Q4 of this revision task contains Ka, which is not part of this course. It contains questions on volumetric analysis and electrolysis.
Revision task 3 Solutions - It contains questions on volumetric analysis, spectroscopy, fuel cells, galvanic cells, calorimetry and electrolysis.
Revision task 4 Solutions - It contains questions on volumetric analysis, galvanic cells, fuel cells, fuels and calorimetry..
Revision task 5 Solutions - It contains questions on equilibrium, experimental technique, enthalpy and calorimetry.
Revision task 6 Solutions - It contains questions on analytical chemistry, organic, experimental technique, thermochemistry, fuel cells.

Revision task 7 Solutions- It contains questions on experimental technique,organic pathways, organic naming, equilibrium.