Topic 15: Organic Chemistry: Carbonyls, Carboxylic Acids and Chirality

Know that optical isomerism is a result of chirality in molecules with a single chiral centre.

Use —optical isomerism is a result of chirality in molecules with a single chiral centre to connect the rule to the data and decision in the question.

This matters because —optical isomerism is a result of chirality in molecules with a single chiral centre determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —optical isomerism is a result of chirality in molecules with a single chiral centre to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Optical isomerism is a result of chirality in molecules with a single chiral centre is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand that optical isomerism results from chiral centre(s) in a molecule with asymmetric carbon atom(s) and that optical isomers (enantiomers) are object and non-superimposable mirror images and be able to draw 3D diagrams of these optical isomers.

Use —optical isomerism results from chiral centre(s) in a molecule with asymmetric carbon atom(s) and that optical isomers to connect the rule to the data and decision in the question.

This matters because —optical isomerism results from chiral centre(s) in a molecule with asymmetric carbon atom(s) and that optical isomers determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —optical isomerism results from chiral centre(s) in a molecule with asymmetric carbon atom(s) and that optical isomers to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Optical isomerism results from chiral centre(s) in a molecule with asymmetric carbon atom(s) and that optical isomers is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Know that optical activity is the ability of a single optical isomer to rotate the plane of polarisation of plane-polarised monochromatic light in molecules containing a single chiral centre.

Use —optical activity is the ability of a single optical isomer to rotate the plane of polarisation of plane-polarised to connect the rule to the data and decision in the question.

This matters because —optical activity is the ability of a single optical isomer to rotate the plane of polarisation of plane-polarised determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —optical activity is the ability of a single optical isomer to rotate the plane of polarisation of plane-polarised to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Optical activity is the ability of a single optical isomer to rotate the plane of polarisation of plane-polarised is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Know what is meant by the term ‘racemic mixture’.

Use —what is meant by the term ‘racemic mixture’ to connect the rule to the data and decision in the question.

This matters because —what is meant by the term ‘racemic mixture’ determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —what is meant by the term ‘racemic mixture’ to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —What is meant by the term ‘racemic mixture’ is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Be able to use data on optical activity of reactants and products as evidence for SN1 and SN2 mechanisms and addition to carbonyl compounds 15B: Carbonyl compounds Students will be assessed on their ability to:.

Use —data on optical activity of reactants and products as evidence for sn1 and sn2 mechanisms and addition to carbonyl compounds to connect the rule to the data and decision in the question.

This matters because —data on optical activity of reactants and products as evidence for sn1 and sn2 mechanisms and addition to carbonyl compounds determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —data on optical activity of reactants and products as evidence for sn1 and sn2 mechanisms and addition to carbonyl compounds to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Data on optical activity of reactants and products as evidence for SN1 and SN2 mechanisms and addition to carbonyl compounds is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the nomenclature of aldehydes and ketones and be able to draw their structural, displayed and skeletal formulae.

Use —the nomenclature of aldehydes and ketones to connect the rule to the data and decision in the question.

This matters because —the nomenclature of aldehydes and ketones determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the nomenclature of aldehydes and ketones to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The nomenclature of aldehydes and ketones is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand that aldehydes and ketones: i do not form intermolecular hydrogen bonds and this affects their physical properties ii can form hydrogen bonds with water and this affects their solubility.

Use —aldehydes and ketones: i do not form intermolecular hydrogen bonds and this affects their physical properties ii can form to connect the rule to the data and decision in the question.

This matters because —aldehydes and ketones: i do not form intermolecular hydrogen bonds and this affects their physical properties ii can form determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —aldehydes and ketones: i do not form intermolecular hydrogen bonds and this affects their physical properties ii can form to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Aldehydes and ketones: i do not form intermolecular hydrogen bonds and this affects their physical properties ii can form is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the reactions of carbonyl compounds with: i Fehling’s or Benedict’s solution, Tollens’ reagent and acidified dichromate(VI) ions In equations, the oxidising agent can be represented as [O]. ii lithium tetrahydridoaluminate(III) (lithium aluminium hydride) in dry ether (ethoxyethane) In equations, the reducing agent can be represented by [H]. iii HCN, in the presence of KCN, as a nucleophilic addition reaction, using curly arrows, relevant lone pairs, dipoles and evidence of optical activity to show the mechanism iv 2,4-dinitrophenylhydrazine (2,4-DNPH), as a qualitative test for the presence of a carbonyl group and to identify a carbonyl compound given data of the melting temperatures of derivatives The equation for this reaction is not required. v iodine in the presence of alkali (the iodoform test).

Use —the reactions of carbonyl compounds with: i fehling’s or benedict’s solution, tollens’ reagent and acidified dichromate(vi) to connect the rule to the data and decision in the question.

This matters because —the reactions of carbonyl compounds with: i fehling’s or benedict’s solution, tollens’ reagent and acidified dichromate(vi) determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the reactions of carbonyl compounds with: i fehling’s or benedict’s solution, tollens’ reagent and acidified dichromate(vi) to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The reactions of carbonyl compounds with: i Fehling’s or Benedict’s solution, Tollens’ reagent and acidified dichromate(VI) is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the nomenclature of carboxylic acids and be able to draw their structural, displayed and skeletal formulae.

Use —the nomenclature of carboxylic acids to connect the rule to the data and decision in the question.

This matters because —the nomenclature of carboxylic acids determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the nomenclature of carboxylic acids to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The nomenclature of carboxylic acids is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand that hydrogen bonding affects the physical properties of carboxylic acids, in relation to their boiling temperatures and solubility.

Use —hydrogen bonding affects the physical properties of carboxylic acids, in relation to their boiling temperatures to connect the rule to the data and decision in the question.

This matters because —hydrogen bonding affects the physical properties of carboxylic acids, in relation to their boiling temperatures determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —hydrogen bonding affects the physical properties of carboxylic acids, in relation to their boiling temperatures to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Hydrogen bonding affects the physical properties of carboxylic acids, in relation to their boiling temperatures is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand that carboxylic acids can be prepared by the oxidation of alcohols or aldehydes and the hydrolysis of nitriles.

Use —carboxylic acids can be prepared by the oxidation of alcohols or aldehydes and the hydrolysis of nitriles to connect the rule to the data and decision in the question.

This matters because —carboxylic acids can be prepared by the oxidation of alcohols or aldehydes and the hydrolysis of nitriles determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —carboxylic acids can be prepared by the oxidation of alcohols or aldehydes and the hydrolysis of nitriles to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Carboxylic acids can be prepared by the oxidation of alcohols or aldehydes and the hydrolysis of nitriles is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the reactions of carboxylic acids with: i lithium tetrahydridoaluminate(III) (lithium aluminium hydride) in dry ether (ethoxyethane) ii bases to produce salts iii phosphorus(V) chloride (phosphorus pentachloride) iv alcohols in the presence of an acid catalyst.

Use —the reactions of carboxylic acids with: i lithium tetrahydridoaluminate(iii) (lithium aluminium hydride) in dry ether to connect the rule to the data and decision in the question.

This matters because —the reactions of carboxylic acids with: i lithium tetrahydridoaluminate(iii) (lithium aluminium hydride) in dry ether determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the reactions of carboxylic acids with: i lithium tetrahydridoaluminate(iii) (lithium aluminium hydride) in dry ether to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The reactions of carboxylic acids with: i lithium tetrahydridoaluminate(III) (lithium aluminium hydride) in dry ether is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the nomenclature of acyl chlorides and esters and be able to draw their structural, displayed and skeletal formulae.

Use —the nomenclature of acyl chlorides and esters to connect the rule to the data and decision in the question.

This matters because —the nomenclature of acyl chlorides and esters determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the nomenclature of acyl chlorides and esters to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The nomenclature of acyl chlorides and esters is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the reactions of acyl chlorides with: i water ii alcohols iii concentrated ammonia iv amines.

Use —the reactions of acyl chlorides with: i water ii alcohols iii concentrated ammonia iv amines to connect the rule to the data and decision in the question.

This matters because —the reactions of acyl chlorides with: i water ii alcohols iii concentrated ammonia iv amines determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the reactions of acyl chlorides with: i water ii alcohols iii concentrated ammonia iv amines to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The reactions of acyl chlorides with: i water ii alcohols iii concentrated ammonia iv amines is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the hydrolysis reactions of esters, in acidic and alkaline solution.

Use —the hydrolysis reactions of esters, in acidic and alkaline solution to connect the rule to the data and decision in the question.

This matters because —the hydrolysis reactions of esters, in acidic and alkaline solution determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the hydrolysis reactions of esters, in acidic and alkaline solution to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The hydrolysis reactions of esters, in acidic and alkaline solution is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand how polyesters, such as terylene, are formed by condensation polymerisation reactions.

Use —how polyesters, such as terylene, are formed by condensation polymerisation reactions to connect the rule to the data and decision in the question.

This matters because —how polyesters, such as terylene, are formed by condensation polymerisation reactions determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —how polyesters, such as terylene, are formed by condensation polymerisation reactions to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —How polyesters, such as terylene, are formed by condensation polymerisation reactions is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Be able to use data from mass spectra to: i suggest possible structures of a simple organic compound given accurate relative molecular masses ii calculate the accurate relative molecular mass of a compound, given accurate relative atomic masses to four decimal places.

Use —data from mass spectra to: i suggest possible structures of a simple organic compound given accurate relative molecular to connect the rule to the data and decision in the question.

This matters because —data from mass spectra to: i suggest possible structures of a simple organic compound given accurate relative molecular determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —data from mass spectra to: i suggest possible structures of a simple organic compound given accurate relative molecular to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Data from mass spectra to: i suggest possible structures of a simple organic compound given accurate relative molecular is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand that carbon-13, (13C) NMR spectroscopy provides information about the positions of 13C atoms in a molecule.

Use —carbon-13, (13c) nmr spectroscopy provides information about the positions of 13c atoms in a molecule to connect the rule to the data and decision in the question.

This matters because —carbon-13, (13c) nmr spectroscopy provides information about the positions of 13c atoms in a molecule determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —carbon-13, (13c) nmr spectroscopy provides information about the positions of 13c atoms in a molecule to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Carbon-13, (13C) NMR spectroscopy provides information about the positions of 13C atoms in a molecule is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Be able to use data from 13C NMR spectroscopy to: i predict the different environments for carbon atoms present in a molecule, given values of chemical shift, δ ii justify the number of peaks present in a 13C NMR spectrum in terms of the number of carbon atoms in different environments.

Use —data from 13c nmr spectroscopy to: i predict the different environments for carbon atoms present in a molecule, given values to connect the rule to the data and decision in the question.

This matters because —data from 13c nmr spectroscopy to: i predict the different environments for carbon atoms present in a molecule, given values determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —data from 13c nmr spectroscopy to: i predict the different environments for carbon atoms present in a molecule, given values to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Data from 13C NMR spectroscopy to: i predict the different environments for carbon atoms present in a molecule, given values is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Be able to use both low and high resolution proton NMR spectroscopy to: i predict the different types of proton present in a molecule, given values of chemical shift, δ ii relate relative peak areas, or ratio number of protons, to the relative numbers of 1H atoms in different environments iii deduce the splitting patterns of adjacent, non-equivalent protons using the (n+1) rule and hence suggest the possible structures for a molecule iv predict the chemical shifts and splitting patterns of the 1H atoms in a given molecule.

Use —both low and high resolution proton nmr spectroscopy to: i predict the different types of proton present in a molecule to connect the rule to the data and decision in the question.

This matters because —both low and high resolution proton nmr spectroscopy to: i predict the different types of proton present in a molecule determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —both low and high resolution proton nmr spectroscopy to: i predict the different types of proton present in a molecule to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Both low and high resolution proton NMR spectroscopy to: i predict the different types of proton present in a molecule is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Know that chromatography separates components of a mixture using a mobile phase and a stationary phase.

Use —chromatography separates components of a mixture using a mobile phase and a stationary phase to connect the rule to the data and decision in the question.

This matters because —chromatography separates components of a mixture using a mobile phase and a stationary phase determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —chromatography separates components of a mixture using a mobile phase and a stationary phase to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Chromatography separates components of a mixture using a mobile phase and a stationary phase is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Be able to calculate Rf values from one-way chromatograms in paper and thin-layer chromatography (TLC) and understand reasons for differences in Rf values.

Use —rf values from one-way chromatograms in paper and thin-layer chromatography (tlc) and understand reasons for differences to connect the rule to the data and decision in the question.

This matters because —rf values from one-way chromatograms in paper and thin-layer chromatography (tlc) and understand reasons for differences determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —rf values from one-way chromatograms in paper and thin-layer chromatography (tlc) and understand reasons for differences to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Rf values from one-way chromatograms in paper and thin-layer chromatography (TLC) and understand reasons for differences is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Know that high-performance liquid chromatography, HPLC, and gas chromatography, GC, are types of column chromatography that separate substances because of different retention times in the column and may be used in conjunction with mass spectrometry, in applications such as forensics or drug testing in sport.

Use —high-performance liquid chromatography, hplc, and gas chromatography, gc, are types of column chromatography that separate to connect the rule to the data and decision in the question.

This matters because —high-performance liquid chromatography, hplc, and gas chromatography, gc, are types of column chromatography that separate determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —high-performance liquid chromatography, hplc, and gas chromatography, gc, are types of column chromatography that separate to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —High-performance liquid chromatography, HPLC, and gas chromatography, GC, are types of column chromatography that separate is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.