5.7Unit 5. Transition Metals and Organic Nitrogen Chemistry
Organic Synthesis — IAL Edexcel Linear (Chemistry) Revision Notes & Topical Questions
15 min read 29 parts Lesson 6 of 43 1 quiz
Curriculum Equation Key قوانين الرقم الهيدروجيني والاتزان الأيوني - pH & Acid-Base Equilibrium FormulasFast Exam Solution
pH = -log[H⁺] | pOH = -log[OH⁻] | pH + pOH = 14 | [H⁺][OH⁻] = 10⁻¹⁴
Word Equation & Conditions: الرقم الهيدروجيني = -لوغاريتم تركيز أيون الهيدروجين | pH + pOH = 14
Location & Specifications: الاتزان الأيوني، كيمياء 3 ثانوي، التحصيلي، و AP Chemistry.
Lesson summary
5.7 Organic Synthesis — Overview, Structure Deduction and Chain Lengthening — IAL EDEXCEL LINEAR (CHEMISTRY) notes: Deduce organic structures from reaction and spectral data, plan multi-step routes and lengthen carbon chains.Step 1 — find the empirical formula from combustion or …
- Infrared spectroscopy
- Mass spectrometry
- Target and starting molecule
- Functional group changes
- Retrosynthesis
- Number of steps
Part 1 of 9Order of structure deduction
1Step 1
- Step 1 find the empirical formula from combustion or percentage composition data.
2Step 2
- Step 2 find the molecular formula using the relative molecular mass from mass spectrometry.
3Step 3
- Step 3 identify the functional groups present from test-tube reactions and infrared spectra.
4Step 4
- Step 4 deduce the overall structure from mass spectrum fragments, 13C NMR and 1H NMR.
Part 2 of 9Combustion analysis
Method
- Method a known mass of compound is burned in excess dry oxygen and the CO2 and H2O produced are weighed.
Mass of C
- Mass of C equals 12.0/44.0 × mass of CO2 formed.
- Mass of H — equals 2.0/18.0 × mass of H2O formed (two H atoms per water molecule).
- Mass of O — found by difference, as 100% minus %C minus %H.
Empirical formula
- Empirical formula obtained by dividing each percentage by the relative atomic mass and then by the smallest ratio.
Part 3 of 9Test-tube reactions for functional groups
| Reagent | Group detected | Positive result |
|---|---|---|
| Bromine water | C=C | Orange solution decolourises |
| Acidified potassium dichromate(VI) | Primary or secondary alcohol (or aldehyde) | Orange to green |
| Tollens' reagent | Aldehyde | Silver mirror |
| Fehling's solution | Aldehyde | Blue to red-brown precipitate |
| 2,4-DNPH | C=O in aldehydes and ketones | Orange precipitate |
| Sodium carbonate or NaHCO3 | Carboxylic acid | Effervescence of CO2 |
| Iodine with NaOH (iodoform) | CH3C=O or CH3CH(OH) group | Pale yellow precipitate of CHI3 |
| PCl5 | –OH group | Steamy fumes of HCl |
Part 4 of 9Spectral evidence
Infrared spectroscopy
- Infrared spectroscopy identifies functional groups from characteristic bond absorptions.
Mass spectrometry
- Mass spectrometry gives the molecular ion peak for the molecular formula and fragment peaks for the structure.
13C NMR
- 13C NMR shows the number of different carbon environments in the molecule.
1H NMR
- 1H NMR shows the number of proton environments, their ratios from the integration and the neighbouring protons from splitting.
Part 5 of 9Planning a synthetic route
1Target and starting molecule
- Target and starting molecule draw both and compare the number of carbon atoms.
2Functional group changes
- Functional group changes list each change and match it to a known reaction with its reagents and conditions.
3Retrosynthesis
- Retrosynthesis work backwards from the target to compounds that can be made from the starting material.
4Number of steps
- Number of steps keep the route as short as possible, because the overall yield falls with every step.
5Hazards
- Hazards choose control measures from the hazard data of the reagents.
Part 6 of 9Lengthening the carbon chain
| Method | Reagents and conditions | Product | Carbons added |
|---|---|---|---|
| Halogenoalkane + cyanide | KCN in ethanol, heat under reflux | Nitrile | 1 |
| Carbonyl + HCN | HCN or KCN with acid, buffered | Hydroxynitrile | 1 |
| Grignard + CO2 | RMgX in dry ether, then dilute acid | Carboxylic acid | R group + 1 |
| Grignard + carbonyl | RMgX in dry ether, then dilute acid | Alcohol | R group |
1Nitrile hydrolysis
- RCN + 2H2O + H+ → RCOOH + NH4+ on heating with dilute acid.
2Nitrile reduction
- RCN + 4[H] → RCH2NH2 using LiAlH4 in dry ether.
Part 7 of 9Grignard reagents
Preparation
- Preparation a halogenoalkane reacts with magnesium in dry ether to give RMgX.
Conditions
- Conditions dry apparatus is essential because water protonates the reagent to an alkane.
Methanal
- Methanal gives a primary alcohol.
Other aldehydes
- Other aldehydes give secondary alcohols.
Ketones
- Ketones give tertiary alcohols.
Carbon dioxide
- Carbon dioxide gives a carboxylic acid.
Part 8 of 9Preparation and purification overview
Preparation
- Preparation heat under reflux to complete a slow reaction without loss, or distil off a product as it forms.
Liquids
- Liquids wash in a separating funnel, dry with an anhydrous salt, filter or decant, then redistil at the expected boiling point.
Solids
- Solids recrystallise from the minimum hot solvent and filter under reduced pressure.
Purity
- Purity a sharp melting point matching the data book value, a single TLC spot and no extra peaks in spectra.
Part 9 of 9More from the specification
Nucleophilic substitution
- Nucleophilic substitution a nucleophile replaces the halogen in a haloalkane, for example hydroxide forming an alcohol
Distillation
- Distillation separates a product of lower boiling point from the mixture, with the thermometer at the vapour temperature and a condenser to cool it
Separating a layer
- Separating a layer a separating funnel splits the organic layer from the aqueous one, followed by drying with anhydrous salt
Analysis of the sample
- Analysis of the sample boiling point, melting point and spectra show purity, and reflux keeps the mixture at a constant temperature
Electrophilic substitution
- Replacement of H on the ring by an electrophile.
Nucleophilic substitution
- Replacement of an atom or group by a nucleophile.
Simple distillation
- Separating a solvent from a solution by evaporating and condensing it.
Drying agent
- An anhydrous salt that removes water from an organic liquid.
Distillation
- Separating a liquid from a solution by boiling and condensing the vapour.
Substitution
- One atom or group is replaced by another.
Condenser
- Apparatus that cools gas back to liquid.
Temperature
- A measure of the average kinetic energy of the particles.
Mixture
- Two or more substances mixed but not chemically combined.
Combustion analysis
- Burning a known mass of compound in excess oxygen and weighing the CO2 and H2O formed.
Key terms
| Term | Meaning |
|---|---|
| Synthetic route | A sequence of reactions converting a starting material into a target molecule. |
| Retrosynthesis | Working backwards from the target molecule to suitable starting materials and steps. |
| Nitrile | A compound containing the C≡N group, used to add one carbon to a chain. |
| Hydroxynitrile | A compound with both OH and CN groups, formed when HCN adds to an aldehyde or ketone. |
| Grignard reagent | An organomagnesium halide RMgX made from a halogenoalkane and magnesium in dry ether. |
| Empirical formula | The simplest whole-number ratio of atoms of each element in a compound. |
| Percentage yield | Actual yield divided by theoretical yield × 100. |
Avoid these mistakes
1
Using bromine water to identify an alcohol — it only detects C=C, so use acidified dichromate for alcohols.
2
Using water as the solvent for a Grignard reagent — water destroys it, so dry ether must be used.
3
Stopping nitrile hydrolysis at the amide — heating with dilute acid gives the carboxylic acid.
4
Forgetting the extra carbon from cyanide — each KCN substitution lengthens the chain by one carbon.
Marked practiceQuizzes for this lesson
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