Timeline VCE

Chemistry Unit 4
How are organic compounds categorised analysed and used?

2017-2021


The carbon atom has unique characteristics that explain the diversity and number of organic compounds that not only constitute living tissues but are also found in the fuels, foods, medicines and many of the materials we use in everyday life. In this unit students investigate the structural features, bonding, typical reactions and uses of the major families of organic compounds including those found in food. Students study the ways in which organic structures are represented and named. They process data from instrumental analyses of organic compounds to confirm or deduce organic structures, and perform volumetric analyses to determine the concentrations of organic chemicals in mixtures. Students consider the nature of the reactions involved to predict the products of reaction pathways and to design pathways to produce particular
compounds from given starting materials. Students investigate key food molecules through an exploration of their chemical structures, the hydrolytic reactions in which they are broken down and the condensation reactions in which they are rebuilt to form new molecules. In this context the role of enzymes and coenzymes in facilitating chemical reactions is explored. Students use calorimetry as an investigative tool to determine the energy released in the combustion of foods. A student practical investigation related to energy and/or food is undertaken in either Unit 3 or in Unit 4, or across both Units 3 and 4, and is assessed in Unit 4, Outcome 3. The findings of the investigation are presented
in a scientific poster format as outlined in the template on page 11 of the VCAA study design guide..
AREA OF STUDY 1

How can the diversity of carbon compounds be explained and categorised? In this area of study students explore why such a vast range of carbon compounds is possible. They examine the structural features of members of several homologous series of compounds, including some of the simpler structural isomers, and learn how they are represented and named. Students investigate trends in the physical and chemical properties of various organic families of compounds. They study typical reactions of organic families and some of their reaction pathways, and write balanced chemical equations for organic syntheses. Students learn to deduce or confirm the structure and identity of organic compounds by interpreting data from mass spectrometry, infrared spectroscopy and proton and carbon-13 nuclear magnetic resonance spectroscopy.
Outcome 1
On completion of this unit the student should be able to compare the general structures and reactions of the major organic families of compounds, deduce structures of organic compounds using instrumental analysis data, and design reaction pathways for the synthesis of organic molecules. To achieve this outcome the student will draw on key knowledge outlined in Area of Study 1 and the related
key skills
Week
key knowledge
Topics and Lessons

Resources/Activities

(activities listed in no particular order)

 


Structure and nomenclature of organic compounds
• the carbon atom with reference to valence number, bond strength, stability of carbon bonds with other elements and the formation of isomers (structural and stereoisomers) to explain carbon compound diversity, including identification of chiral centres in optical isomers of simple organic compounds and distinction between cis- and trans- isomers in simple geometric isomers

• structures including molecular, structural and semi-structural formulas of alkanes (including cyclohexane), alkenes, alkynes, benzene, haloalkanes, primary amines, primary amides, alcohols (primary, secondary, tertiary), aldehydes, ketones, carboxylic acids and non-branched esters

• 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, alcohols (primary, secondary, tertiary), carboxylic acids and non-branched esters.
Lesson 1 Solutions - simple naming of hydrocarbons
Lesson 2 Solutions - naming hydrocarbons with more than one functional group
Lesson 3 Solutions - esters
Lesson 4 Solutions -trans and cis isomers
Lesson 5 Solutions -identifying chiral molecules

Categories, properties and reactions of organic compounds
• an explanation of trends in physical properties (boiling point, viscosity) and flashpoint with reference to structure and bonding

Lesson 6 Solutions - trends of organic molecules

• organic reactions, including appropriate equations and reagents, for the oxidation of primary and secondary alcohols, substitution reactions of haloalkanes, addition reactions of alkenes, hydrolysis reactions of esters, the condensation reaction between an amine and a carboxylic acid, and the esterification reaction between an alcohol and a carboxylic acid
Lesson 7 Solutions Oxidation of primary and secondary alcohols


• the pathways used to synthesise primary haloalkanes, primary alcohols, primary amines, carboxylic acids and esters, including calculations of atom economy and percentage yield of single-step or overall pathway reactions.

Lesson 8 solutions - 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.


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

Ongoing revision task 2 Solutions - equilbrium, 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, electroytic cells and reaction pathways.

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



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

Activity-making esters

Organic past exam questions


2018 NHT
2017
VCE
2016
VCE
2015
VCE
2014 VCE
2013
VCE
2012
VCE
2011
VCE
2010
VCE
2010
HSC
2009
VCE
2009 HSC
2008 VCE
2007 VCE
2006
VCE



 

Analysis of organic compounds


• the principles and applications of mass spectroscopy (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

Mass Spectroscopy

Quiz 1 Solution
Quiz 2 Solution
Quiz 3 Solution

Spectroscopy test

Solutions

Spectroscopy past exam questions

2018 NHT
2017 VCE
2016
VCE
2015 VCE
2014 VCE
2013 VCE
2012 VCE
2011 VCE
2010
VCE
2010 HSC
2009
VCE
2009
HSC
2008 VCE
2007 VCE

• the principles (including spin energy levels) and applications of proton and carbon-13 nuclear magnetic resonance spectroscopy (NMR) (excluding features of instrumentation and operation); analysis of carbon-13 NMR spectra
and use of chemical shifts to determine number and nature of different carbon environments in a simple organic compound; and analysis of high resolution proton NMR spectra to determine the structure of a simple organic compound using chemical shifts, areas under peak and peak splitting patterns (excluding coupling constants) and application of the n+1 rule
Lesson 1 Solutions Introduction to HNMR, terms
Lesson 2 Solutions Introduction to NMR spectra and the n+1 rule
Lesson 3 Solutions Problems involving spectra and the n+1 rule.
Lesson 4 Solutions Interpreting the spectra and deriving the molecular structure.

Lesson 5 Solutions 13CNMR spectra

Ongoing revision task 8 Solutions - interpreting 1HNMR spectra, percentage yield, reaction pathways.
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

• the principles and applications of infrared spectroscopy (IR) (excluding features of instrumentation and operation) and interpretation of qualitative and quantitative data including use of characteristic absorption bands to identify bonds

Lesson 1 Solutions - IR spectroscopy

 

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

• determination of the structures of simple organic compounds using a combination of mass spectrometry (MS), infrared spectroscopy (IR) and proton and carbon-13 nuclear magnetic resonance spectroscopy (NMR) (limited to data analysis)

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

 

Summary of analytical techniques.

Yet another summary


Keep in mind-emission and absorption spectroscopy as well as gravimetric analysis are no longer part of this course.

• the principles of chromatography including use of high performance liquid chromatography (HPLC) and construction and use of a calibration curve to determine the concentration of an organic compound in a solution
Lesson 1

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

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

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.

2018 NHT
2017 VCE
2016
VCE
2015 VCE
2014 VCE
2013 VCE
2012 VCE
2011
VCE
2010
VCE
2009
VCE
2008
VCE
2007 VCE
2006 VCE


• determination of the concentration of an organic compound by volumetric analysis, including the principles of direct acid-base and redox titrations (excluding back titrations)

Lesson 1 Solutions - volumetric analysis

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

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
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

Quiz 5 Solution

Quiz 6 Solutions

Revision volumetric analysis Solution

Revision volumetric analysis Solution

Try some worksheets on:

titration

Analysis of ammonia in household cleaner

Available chlorine in household cleaner

Volumetric analysis from past exams.
2018 NHT
2016 VCE
2015 VCE
2014 VCE
2013 VCE
2012
VCE
2011
VCE
2010
VCE
2010
HSC
2009
VCE
2009
HSC
2008 VCE
2007 VCE
2006
VCE
2005
VCE

   
 

AREA OF STUDY 2
Food contains various organic compounds that are the source of both the energy and the raw materials that the human body needs for growth and repair. In this area of study students explore the importance of food from a chemical perspective. Students study the major components of food with reference to their structures, properties and functions. They examine the hydrolysis reactions in which foods are broken down, the condensation reactions in which new biomolecules are formed and the role of enzymes, assisted by coenzymes, in the metabolism of food. Students study the role of glucose in cellular respiration and investigate the principles of calorimetry and its
application in determining enthalpy changes for reactions in solution. They explore applications of food chemistry by considering the differences in structures of natural and artificial sweeteners, the chemical significance of the glycaemic index of foods, the rancidity of fats and oils, and the use of the term 'essential' to describe some amino acids and fatty acids in the diet.

Outcome 2
On completion of this unit the student should be able to distinguish between the chemical structures of key food molecules, analyse the chemical reactions involved in the metabolism of the major components of food including the role of enzymes, and calculate the energy content of food using calorimetry.

 


Key food molecules
• proteins: formation of dipeptides and polypeptides as condensation polymers of 2-amino acids; primary(including peptide links), secondary, tertiary and quaternary structure and bonding; distinction between
essential and non-essential amino acids as dietary components

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

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

Activity-making biodiesel

Synthesis of Aspirin

 

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


2017 VCE
2016
VCE
2015 VCE
2014 VCE
2013 VCE
2012
VCE
2011
VCE
2010
VCE
2010
HSC
2009
VCE
2008 VCE

• carbohydrates: formation of disaccharides from monosaccharides, and of complex carbohydrates (specifically starch and cellulose) as condensation polymers of monosaccharides; glycosidic links; storage of excess glucose in the body as glycogen; comparison of glucose, fructose, sucrose and the artificial sweeteneraspartame with reference to their structures and energy content

Lesson 1 Solutions - carbohydrates

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

• fats and oils (triglycerides): common structural features including ester links; distinction between fats and oils with reference to melting points; explanation of different melting points of triglycerides with reference to the structures of their fatty acid tails and the strength of intermolecular forces; chemical structures of saturated and unsaturated (monounsaturated and polyunsaturated) fatty acids; distinction between essential and nonessential fatty acids; and structural differences between omega-3 fatty acids and omega-6 fatty acids

Lesson 1 Solutions - fats and oils

Fats-Triglycerides

Fatty acids

 

• vitamins: inability of humans to synthesise most vitamins (except Vitamin D) making them essential dietary requirements; comparison of structural features of Vitamin C (illustrative of a water-soluble vitamin) and Vitamin D (illustrative of a fat-soluble vitamin) that determine their solubility in water or oil.
Lesson 1 - Vitamins

Vitamins

Ongoing revision task 11 Solutions - %atom economy, volumetric analysis, food chemistry

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

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

 

Metabolism of food in the human body
• metabolism of food as a source of energy and raw materials: general principles of metabolism of food involving enzyme-catalysed chemical reactions with reference to the breakdown of large biomolecules in food by hydrolytic reactions to produce smaller molecules, and the subsequent synthesis of large biologically important molecules by condensation reactions of smaller molecules
• enzymes as protein catalysts: active site; modelling of process by which enzymes control specific biochemical reactions (lock-and-key and induced fit models); consequences of variation in enzyme-substrate interaction (lock-and-key mechanism) due to the behaviour of a particular optical isomer; explanation of effects of changes in pH (formation of zwitterions and denaturation), increased temperature (denaturation) and decreased temperature (reduction in activity) on enzyme activity with reference to structure and bonding; action of enzymes in narrow pH
ranges; and use of reaction rates to measure enzyme activity
• the distinction between denaturation of a protein and hydrolysis of its primary structure
• hydrolysis of starch in the body: explanation of the ability of all humans to hydrolyse starch but not cellulose, and of differential ability in humans to hydrolyse lactose; glycaemic index (GI) of foods as a ranking of carbohydrates based on the hydrolysis of starches (varying proportions of amylose and amylopectin) to produce glucose in the body
• hydrolysis of fats and oils from foods to produce glycerol and fatty acids; oxidative rancidity with reference to chemical reactions and processes, and the role of antioxidants in slowing rate of oxidative rancidity
• the principles of the action of coenzymes (often derived from vitamins) as organic molecules that bind to the active site of an enzyme during catalysis, thereby changing the surface shape and hence the binding properties of the active site to enable function as intermediate carriers of electrons and/or groups of atoms (no specific cases required).

Lesson 1 Solutions - hydrolysis reactions of food molecules

Lesson 2 Solutions - enzymes

Lesson 3 Solutions - Rancidity

Enzymes

Hydrolysis

Metabolism of macromolecules

Glycaemic index

  Energy content of food
• the comparison of energy values of carbohydrates, proteins and fats and oils
• glucose as the primary energy source, including a balanced thermochemical equation for cellular respiration
• the principles of calorimetry; solution and bomb calorimetry, including determination of calibration factor and consideration of the effects of heat loss; and analysis of temperature-time graphs obtained from solution calorimetry.
Lesson 1 Solutions - calorimetry - temperature time graphs

Calorimetry

Quiz 1 Solutions

Quiz 2 Solutions

Quiz 3 Solutions

Quiz 4 Solutions

Quiz 5 Solutions

The list below includes enthalpy questions from past exams

2018 NHT
2016 VCE
2015 VCE
2014 VCE
2013 VCE
2012
VCE
2011
VCE
2010
VCE
2010
HSC
2009
VCE
2009
HSC
2008
VCE
2007
VCE
2006
VCE
2005 VCE

  AREA OF STUDY 3
 

Practical investigation

A student-designed or adapted practical investigation related to energy and/or food is undertaken in either Unit 3 or Unit 4, or across both Units 3 and 4. The investigation relates to knowledge and skills developed across Unit 3 and/or Unit 4.
The investigation requires the student to identify an aim, develop a question, formulate a hypothesis and plan a course of action to answer the question and that complies with safety and ethical requirements. The student then undertakes an experiment that involves the collection of primary qualitative and/or quantitative data, analyses and evaluates the data, identifies limitations of data and methods, links experimental results to science ideas, reaches a conclusion in response to the question and suggests further investigations which may be undertaken.

Findings are communicated in a scientific poster format according to the template on page 11 of the study design . A practical logbook must
be maintained by the student for record, authentication and assessment purposes.

Experimental technique

Quiz 1 Solutions

Quiz 2 Solutions

Experimental technique (ET)

 

2018 NHT(ET)
2017 VCE (ET)
2016
VCE (ET)

Application of chemical knowledge

2017 VCE

   

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 voloumetric analysis, galvanic cells, fuel cells, fuels and calorimetry..
Revision task 5 Solutions - It contains questions on equilibrium, experimental technique, enthalpy and calorimetry.