Here are your complete, exam-ready study notes for all 10 compounds in order!
π ORGANIC CHEMISTRY - STUDY NOTES
PharmD 1st Year | KUHS University
β IMPORTANCE RANKING (for exams):
Most Important: Glyceryl Trinitrate, Dimercaprol, Lactic Acid, Tartaric Acid
Moderately Important: Chlorbutol, Urea, Vanillin, Paraldehyde
Also Important: Ethylenediamine Dihydrate, Ethylene Chloride
βββ COMPOUND 1: CHLORBUTOL (Chlorobutanol)
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | 1,1,1-Trichloro-2-methyl-2-propanol |
| Synonyms | Chlorbutol, Chloretone, Methaform |
| Molecular Formula | CClβC(CHβ)βOH |
| Molecular Weight | 177.46 g/mol |
| Category | Tertiary alcohol + Halogenated compound |
π§ͺ Structure
Cl
|
Cl --- C --- CHβ
| \
Cl C --- OH
|
CHβ
- Central carbon bonded to 3 chlorine atoms
- Secondary carbon bonded to 2 methyl groups and -OH
- It is a tertiary alcohol
βοΈ Preparation
Chlorbutol is prepared by the reaction of chloroform (CHClβ) with acetone ((CHβ)βCO) in the presence of potassium hydroxide (KOH):
CHClβ + (CHβ)βCO β KOH β CClβΒ·C(CHβ)βΒ·OH
- This is a nucleophilic addition reaction
- KOH first converts chloroform to trichloromethyl carbanion (:CClββ»)
- This carbanion attacks the carbonyl carbon of acetone
π¬ Physical Properties
- Appearance: White crystalline solid with camphor-like odour
- Melting point: 95-97Β°C (stable form), 78Β°C (metastable form) - β exam point
- Solubility: Slightly soluble in water; freely soluble in alcohol, ether, chloroform
- Volatility: Volatile - sublimes on heating
- Taste: Slightly bitter
β‘ Chemical Properties & Reactions
1. Hydrolysis (Important!)
Chlorbutol undergoes alkaline hydrolysis to release chloride ions:
CClβΒ·C(CHβ)βΒ·OH + NaOH β Chloride ions detected by AgNOβ test
2. Silver Nitrate Test (Identification)
- Heat with dilute HNOβ + AgNOβ
- White precipitate of AgCl forms
- This confirms presence of organically bound chlorine
3. Resorcinol Test
- Gives characteristic colour reaction with resorcinol in alkaline conditions
4. Action with Alkalis
- Slowly hydrolysed by aqueous alkalis releasing trichloromethanol which breaks down
π Pharmaceutical Uses (β Very Important for Exam)
- Preservative - used as antimicrobial preservative in injections, eye drops, nasal drops (concentration: 0.5%)
- Local anaesthetic - mild numbing effect
- Sedative and hypnotic - older use, now largely replaced
- Antiseptic - dental preparations
- Used in ophthalmic preparations - eye drops
π§ Exam Tips
- "Camphor smell" = Chlorbutol - remember this
- Prepared from chloroform + acetone + KOH
- Identified by AgNOβ test (white precipitate)
- Used as preservative at 0.5% in parenteral preparations
- Has two polymorphic forms (stable & metastable)
ββββ COMPOUND 2: DIMERCAPROL (BAL)
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | 2,3-dimercapto-1-propanol |
| Synonyms | BAL (British Anti-Lewisite) - β must know! |
| Molecular Formula | CβHβOSβ (HSCHβΒ·CH(SH)Β·CHβOH) |
| Molecular Weight | 124.23 g/mol |
| Category | Dithiol compound (contains 2 -SH groups) |
π§ͺ Structure
SH SH
| |
HβC -- CH -- CHβ -- OH
- Position 1: -CHβOH (primary alcohol)
- Position 2: -CH-SH (thiol group)
- Position 3: -CHβ-SH (thiol group)
- Two free -SH (sulfhydryl) groups are the key to its action
βοΈ Preparation
Prepared from allyl alcohol through two steps:
- Allyl alcohol + Brβ β 2,3-dibromopropanol
- 2,3-dibromopropanol + NaHS (sodium hydrosulphide) β Dimercaprol
CHβ=CH-CHβOH β (Brβ) β BrCHβ-CHBr-CHβOH β (NaHS) β HSCHβ-CH(SH)-CHβOH
π¬ Physical Properties
- Appearance: Colourless or pale yellow, oily liquid
- Odour: Very strong, unpleasant garlic-like smell - β exam point
- Boiling point: 80Β°C at 1 mmHg
- Solubility: Soluble in water, alcohol, benzene; insoluble in fixed oils
- Unstable in alkaline aqueous solution - rapidly oxidised in air
β‘ Chemical Properties & Reactions
1. Chelation (Most Important! ββ)
The two -SH groups form stable chelate rings with heavy metal ions:
Dimercaprol + Metal (As, Hg, Pb, Au) β Stable 5-membered chelate ring
S --- Metal
/ \
-CHβ CH-
\ /
S --------
- This 5-membered ring is very stable
- Metal is "grabbed" by both sulfur atoms simultaneously
2. Oxidation
- -SH groups are easily oxidised to disulphide (-S-S-) bonds
- This is why it must be stored in sealed, airtight containers away from air
3. Reaction with Metals
Forms insoluble precipitates with mercury, arsenic, gold, lead, bismuth
4. Sodium Nitroprusside Test (Identification)
- Dimercaprol + sodium nitroprusside β Purple/violet colour (confirms -SH group)
π Pharmaceutical Uses (ββ Most Important Compound)
- Antidote for heavy metal poisoning - primary use! Works for:
- Arsenic poisoning (e.g., lewisite gas - hence "Anti-Lewisite")
- Mercury poisoning
- Lead poisoning (combined with EDTA)
- Gold poisoning (from gold therapy side effects)
- Bismuth poisoning
- NOT effective against iron, cadmium, or selenium poisoning - β exam point
- Dose: 2.5-3 mg/kg IM every 4 hours
π§ Exam Tips
- Full name BAL = British Anti-Lewisite (developed in WWII against lewisite nerve gas) - β
- Has 2 -SH groups that chelate heavy metals
- Forms 5-membered chelate ring
- Garlic odour = Dimercaprol
- NOT used for iron or cadmium poisoning
- Given by IM injection (not oral) because of instability
- Identified by sodium nitroprusside test (purple colour with -SH groups)
βββββ COMPOUND 3: GLYCERYL TRINITRATE (GTN)
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | Propane-1,2,3-triyl trinitrate |
| Synonyms | Nitroglycerin, Trinitrin, GTN |
| Molecular Formula | CβHβ
NβOβ |
| Molecular Weight | 227.09 g/mol |
| Category | Organic nitrate ester |
π§ͺ Structure
O-NOβ
|
HβC --- O-NOβ (wait, correct structure below)
CHβ - O - NOβ
|
CH - O - NOβ
|
CHβ - O - NOβ
- Glycerol backbone (3 carbons)
- All 3 -OH groups replaced by -ONOβ (nitrate ester) groups
- Formula shows it is a triester of nitric acid with glycerol
βοΈ Preparation (β Very Important)
Made by nitration of glycerol using a mixed acid (nitric acid + sulphuric acid):
CβHβ
(OH)β + 3HNOβ β (HβSOβ, below 10Β°C) β CβHβ
(ONOβ)β + 3HβO
- Temperature must be kept below 10Β°C (ice bath) - if temperature rises, EXPLOSION occurs - ββ exam point
- HβSOβ acts as dehydrating agent
- Reaction is highly exothermic
π¬ Physical Properties
- Appearance: Colourless, oily liquid (pale yellow with impurities)
- Taste: Sweet, burning taste causing severe headache if tasted - β
- Density: 1.6 g/mL (heavier than water)
- Solubility: Slightly soluble in water; miscible with alcohol, ether, acetone
- Boiling point: Explodes at ~50-60Β°C - EXTREMELY EXPLOSIVE - ββ
- Sensitivity: Shock, friction, and heat cause explosion
β‘ Chemical Properties & Reactions
1. Explosive Decomposition (ββ Most Important)
4 CβHβ
(ONOβ)β β 12COβ + 10HβO + 6Nβ + Oβ + HEAT
- Releases enormous amount of gas rapidly = EXPLOSION
- This is why it is mixed with diatomite (kieselguhr) to make dynamite (Nobel's invention)
2. Hydrolysis
- Alkaline hydrolysis breaks the nitrate ester bonds:
GTN + NaOH β Glycerol + Sodium nitrate (NaNOβ)
3. Colour Test (FeSOβ Test)
- GTN + FeSOβ in HβSOβ β Brown ring (nitrate test)
4. Reduction
- Reduces to glycerol and liberate nitrogen oxides
π Pharmaceutical Uses (ββ Critical)
- Treatment of Angina Pectoris - most important use! (vasodilator)
- Acute Heart Failure management
- Hypertensive emergencies
- Routes of administration:
- Sublingual tablet - fastest absorption (onset: 1-3 min) - β
- Transdermal patch - sustained release
- IV infusion - in hospital setting
- Buccal tablet
- Mechanism: Releases nitric oxide (NO) β activates guanylate cyclase β increases cGMP β smooth muscle relaxation β vasodilation
π§ Exam Tips
- "Below 10Β°C" during preparation - critical safety measure
- GTN is EXPLOSIVE - handle with extreme care; diluted with lactose for tablets
- Sublingual = fastest route for angina relief
- Headache is a classic side effect (vasodilation of cerebral vessels)
- Mechanism: NO β cGMP β vasodilation
- Used to make dynamite (mixed with kieselguhr)
- Store in cool, dark place in small quantities
βββ COMPOUND 4: UREA (Carbamide)
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | Diaminomethanone / Carbamide |
| Synonyms | Carbamide, Urea |
| Molecular Formula | CO(NHβ)β or CHβNβO |
| Molecular Weight | 60.06 g/mol |
| Category | Diamide of carbonic acid |
π§ͺ Structure
O
β
HβN -- C -- NHβ
- Central carbonyl group (C=O)
- Two amino groups (-NHβ) attached to the carbonyl carbon
- It is the diamide of carbonic acid
βοΈ Preparation
Industrial Method (Bosch-Meiser Process) (β Most Important)
Two-step process:
Step 1: NHβ + COβ β Ammonium carbamate
2NHβ + COβ β NHβCOONHβ (at high pressure, 150-200Β°C)
Step 2: Ammonium carbamate β Urea + Water
NHβCOONHβ β CO(NHβ)β + HβO
Lab Method (WΓΆhler Synthesis - Historical β)
AgNCO + NHβCl β CO(NHβ)β + AgCl
- This was the first ever synthesis of an organic compound from inorganic materials (1828)
- Proved that organic compounds CAN be made in the lab (disproved vitalism theory)
- ββ This is a VERY important historical fact for exams
π¬ Physical Properties
- Appearance: White crystalline solid
- Odour: Odourless
- Taste: Saline (slightly salty) taste
- Melting point: 132-135Β°C
- Solubility: Very freely soluble in water; soluble in alcohol; insoluble in ether, chloroform
- Hygroscopic (absorbs moisture from air)
β‘ Chemical Properties & Reactions
1. Hydrolysis (β Important)
With water (acid/base catalysed or by urease enzyme):
CO(NHβ)β + HβO β COβ + 2NHβ
2. Reaction with Nitrous Acid
CO(NHβ)β + 2HNOβ β COβ + 2Nβ + 3HβO
3. Biuret Formation (β Identification Test)
On heating above melting point:
2CO(NHβ)β β NHβ-CO-NH-CO-NHβ + NHβ (Biuret)
- Biuret + CuSOβ in alkaline solution β Violet/purple colour (Biuret test)
- This confirms peptide bonds/urea
4. Reaction with Dimethylglyoxime
Urea gives a characteristic crystalline precipitate
5. Condensation with Formaldehyde
Urea + HCHO β Urea-formaldehyde resin (plastic)
6. Salt Formation
Being a weak base, urea reacts with acids:
CO(NHβ)β + HNOβ β CO(NHβ)βΒ·HNOβ (Urea nitrate) - white crystals, used in explosives!
π Pharmaceutical Uses
- Diuretic - promotes urine output
- Keratolytic agent - softens and removes hard skin (in creams 10-40%)
- Topical moisturiser - used in dry skin conditions, psoriasis
- Osmotic diuretic - reduces intracranial pressure
- Urea breath test - diagnosis of H. pylori infection (β clinical use)
- Fertilizer - major agricultural use (non-pharmaceutical)
- Urea-formaldehyde resin - industrial plastic
π§ Exam Tips
- WΓΆhler synthesis (1828) = first organic compound from inorganic - MAJOR historical fact ββ
- Biuret test = violet colour with CuSOβ alkali
- Hydrolysis gives COβ + NHβ (urease does this in body)
- Urea is the end product of protein metabolism in humans
- Freely soluble in water (important physical property)
- Used as keratolytic in skin creams
βββ COMPOUND 5: ETHYLENEDIAMINE DIHYDRATE
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | Ethane-1,2-diamine dihydrate |
| Synonyms | EDA, 1,2-Diaminoethane dihydrate |
| Molecular Formula | CβHβNβΒ·2HβO |
| Molecular Weight | 96.11 g/mol (anhydrous: 60.1 g/mol) |
| Category | Aliphatic diamine |
π§ͺ Structure
HβN -- CHβ -- CHβ -- NHβ Β· 2HβO
Or: NHβ-CHβ-CHβ-NHβ (dihydrate form with 2 water molecules)
- Two primary amine groups (-NHβ)
- Separated by an ethylene bridge (-CHβ-CHβ-)
βοΈ Preparation
Prepared from ethylene dichloride (1,2-dichloroethane) and ammonia:
ClCHβCHβCl + 2NHβ β HβN-CHβ-CHβ-NHβ + 2HCl
Or from ethanolamine:
HOCHβCHβNHβ + NHβ β HβN-CHβ-CHβ-NHβ + HβO
π¬ Physical Properties
- Appearance: Colourless to yellowish liquid (dihydrate form)
- Odour: Strong ammonia-like smell - β
- Boiling point: 116Β°C (anhydrous)
- Solubility: Miscible with water and alcohol; slightly soluble in ether
- Strongly alkaline in nature (pH ~11.9)
- Hygroscopic - absorbs COβ from air to form carbonate
β‘ Chemical Properties & Reactions
1. Basic Properties (β)
Both -NHβ groups are basic, can accept protons:
HβN-CHβ-CHβ-NHβ + 2HCl β ClHβN-CHβ-CHβ-NHβCl (ethylenediamine dihydrochloride)
2. Chelation (Important!)
EDA forms chelate complexes with metal ions (eg. CuΒ²βΊ):
- The two nitrogen atoms donate electron pairs to the metal
- Forms 5-membered chelate rings with metals
3. Reaction with COβ
HβN-CHβ-CHβ-NHβ + COβ + HβO β Ethylenediamine carbonate (white solid)
- This is why EDA solutions turn cloudy on standing in air
4. Reaction with Acids
Forms salts: Ethylenediamine dihydrochloride, dihydrobromide, etc.
5. Acylation
Reacts with acid chlorides/anhydrides to form amides
π Pharmaceutical Uses
- Used as a solubiliser for drugs - makes poorly soluble drugs dissolve better
- Example: Aminophylline = Theophylline + Ethylenediamine - ββ classic exam example!
- Chelating agent - complexes with metal ions (component of EDTA-related compounds)
- In synthesis of antihistamines (ethylenediamine antihistamines)
- Example: Pyrilamine, Tripelennamine (Hβ antihistamines) contain EDA structure
- Pharmaceutical excipient in liquid formulations
- Antifungal agent base (e.g., in fungal infections topically)
π§ Exam Tips
- Aminophylline = Theophylline + Ethylenediamine - this is the #1 exam fact ββ
- Has 2 -NHβ groups (diamine)
- Strong ammonia smell
- Forms 5-membered chelate rings with metals
- Used as solubiliser in pharmaceutical formulations
- EDA-type antihistamines: Pyrilamine, Tripelennamine
βββ COMPOUND 6: VANILLIN
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | 4-hydroxy-3-methoxybenzaldehyde |
| Synonyms | Methyl protocatechualdehyde |
| Molecular Formula | CβHβOβ |
| Molecular Weight | 152.15 g/mol |
| Category | Aromatic aldehyde + phenol + ether |
π§ͺ Structure
CHO (aldehyde group at position 1)
|
[Benzene ring]
| |
OH OCHβ
(position 4) (position 3)
Full structural features:
- Benzaldehyde ring (aromatic)
- -OH group (phenolic) at para position
- -OCHβ group (methoxy) at meta position
- -CHO (aldehyde) at position 1
βοΈ Preparation
From Eugenol (Natural Method)
Vanillin is naturally found in vanilla bean (Vanilla planifolia)
Synthetic Method (From Guaiacol) - β
Guaiacol (2-methoxyphenol) + CHClβ/NaOH β (Reimer-Tiemann reaction) β Vanillin
From Catechol:
Catechol + (CHβ)βSOβ β Guaiacol β Vanillin (via oxidation)
From Lignin (Industrial)
Lignin (waste from paper industry) β oxidation β Vanillin (cost-effective industrial source)
π¬ Physical Properties
- Appearance: White to slightly yellowish needle-like crystals
- Odour: Pleasant, characteristic vanilla fragrance - β
- Melting point: 81-83Β°C
- Solubility: Slightly soluble in water; freely soluble in alcohol, ether, chloroform
- Taste: Sweet, characteristic vanilla taste
β‘ Chemical Properties & Reactions
1. Aldehyde Reactions (β)
a) Tollens' Test (Silver Mirror Test):
Vanillin + Tollens' reagent (ammoniacal AgNOβ) β Silver mirror on test tube wall
b) Fehling's Test:
Vanillin + Fehling's solution β Red/brick-red precipitate of CuβO
- Note: Vanillin gives a positive Fehling's test despite being aromatic (due to -CHO)
c) Schiff's Test:
Vanillin + Schiff's reagent (decolourised fuchsin) β Pink/magenta colour
2. Phenolic Reactions (β)
a) FeClβ Test:
Vanillin + FeClβ solution β Blue-green colour
- Confirms phenolic -OH group
b) Bromine Water:
Vanillin + Brβ water β Decolourisation (electrophilic substitution on aromatic ring)
3. Condensation Reactions
With hydroxylamine: Vanillin β Vanillin oxime (vanillal)
With hydrazine: β Vanillin hydrazone
4. Oxidation
Vanillin β (oxidation) β Vanillic acid (4-hydroxy-3-methoxybenzoic acid)
π Pharmaceutical Uses
- Flavouring agent - most widely used; used to mask bitter taste of medicines β
- Perfumery - fragrance ingredient
- Pharmaceutical formulations - syrups, tablets, oral liquids for taste masking
- Food additive - vanilla flavour
- Intermediate in synthesis of L-DOPA (Parkinson's disease drug) and other drugs
π§ Exam Tips
- 3 functional groups: -CHO, -OH (phenol), -OCHβ (methoxy) - β all three in one molecule!
- Gives positive Tollens', Fehling's, and Schiff's test (aldehyde reactions)
- Gives FeClβ blue-green (phenol reaction)
- Used as flavouring agent in pharmacy
- Natural source: Vanilla bean pods
- Industrial source: Lignin (paper mill waste)
- MP = 81-83Β°C (white crystals)
βββ COMPOUND 7: PARALDEHYDE
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | 2,4,6-trimethyl-1,3,5-trioxane |
| Synonyms | Paracetaldehyde, Paraldehyde |
| Molecular Formula | CβHββOβ (or (CHβCHO)β) |
| Molecular Weight | 132.16 g/mol |
| Category | Cyclic trimer of acetaldehyde |
π§ͺ Structure
CHβ
|
O --- CH
/ \
CH O
| |
CHβ CHβ-CH
\ /
O -------
- 6-membered ring containing 3 oxygen and 3 carbon atoms alternating
- Each carbon has a methyl group (-CHβ)
- It is the cyclic trimer of acetaldehyde (CHβCHO)
βοΈ Preparation
Trimerisation of Acetaldehyde:
3 CHβCHO β (HβSOβ/HCl catalyst, cold) β (CHβCHO)β (Paraldehyde)
- Acetaldehyde undergoes acid-catalysed trimerisation
- Cold conditions favour paraldehyde formation
- Warm conditions/excess acid β metaldehyde (tetramer) instead
π¬ Physical Properties
- Appearance: Colourless liquid
- Odour: Strong, unpleasant, disagreeable smell - β
- Taste: Burning, unpleasant taste
- Boiling point: 124Β°C
- Solubility: Sparingly soluble in water; miscible with alcohol, ether, oils
- Density: 0.99 g/mL
β‘ Chemical Properties & Reactions
1. Depolymerisation (β Key Reaction)
Paraldehyde is depolymerised back to acetaldehyde on:
- Heating with dilute acid
- Standing (slow)
(CHβCHO)β β (HβΊ/heat) β 3 CHβCHO
This is why old/oxidised paraldehyde smells of acetic acid (acetaldehyde oxidises to acetic acid)
2. Does NOT give Tollens'/Fehling's Test
- Paraldehyde itself does NOT give silver mirror test (no free -CHO)
- After hydrolysis to acetaldehyde, it gives positive reactions β (exam trick question!)
3. Oxidation
Paraldehyde β (air oxidation, slow) β Acetic acid
- Oxidised paraldehyde is TOXIC and must not be used β
4. Reaction with NaOH
No reaction (unlike aldehydes, no Cannizzaro reaction directly)
π Pharmaceutical Uses
- Anticonvulsant - used in status epilepticus (emergency seizure control) β
- Sedative and hypnotic (older use)
- Alcohol withdrawal - to manage delirium tremens
- Basal narcosis before surgery (historical)
- Routes: Oral, rectal (IM painful and can cause nerve damage)
π§ Exam Tips
- Paraldehyde = trimer of acetaldehyde - this is the core fact β
- No free -CHO group β negative Tollens'/Fehling's test (until hydrolysed!)
- Depolymerises to acetaldehyde with acid/heat
- Old oxidised paraldehyde β acetic acid (toxic, must not use) β
- Used in status epilepticus (medical emergency seizure)
- Unpleasant smell = characteristic
- Store away from light and air (oxidises slowly)
βββ COMPOUND 8: ETHYLENE CHLORIDE (1,2-Dichloroethane)
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | 1,2-Dichloroethane |
| Synonyms | Ethylene dichloride (EDC), Dutch oil |
| Molecular Formula | ClCHβCHβCl (CβHβClβ) |
| Molecular Weight | 98.96 g/mol |
| Category | Vicinal dihalide (halogenated alkane) |
π§ͺ Structure
Cl -- CHβ -- CHβ -- Cl
- Two chlorine atoms on adjacent (1,2) carbons
- Vicinal dichloride (both Cl on neighbouring carbons)
- Gauche and anti conformers exist (free rotation around C-C bond)
βοΈ Preparation
Method 1: Addition of Clβ to Ethylene (β Main Method)
CHβ=CHβ + Clβ β CHβCl-CHβCl
- Electrophilic addition reaction
- No catalyst needed
- Carried out in liquid phase at room temperature
Method 2: Oxychlorination
CHβ=CHβ + 2HCl + Β½Oβ β CHβCl-CHβCl + HβO (industrial)
π¬ Physical Properties
- Appearance: Colourless liquid
- Odour: Sweet, chloroform-like smell β
- Boiling point: 83.5Β°C
- Density: 1.25 g/mL (heavier than water)
- Solubility: Practically insoluble in water; miscible with organic solvents
- Immiscible with water (important for extraction use)
β‘ Chemical Properties & Reactions
1. Nucleophilic Substitution (SN2)
ClCHβCHβCl + 2NaOH β HOCHβCHβOH + 2NaCl (gives ethylene glycol)
2. Elimination (E2)
ClCHβCHβCl + KOH (alcoholic) β CHβ=CHCl + KCl + HβO (vinyl chloride)
Or: β CHβ‘CH + 2KCl + 2HβO (acetylene)
3. Reaction with Ammonia
ClCHβCHβCl + 2NHβ β HβN-CHβ-CHβ-NHβ + 2HCl (Synthesis of Ethylenediamine!)
- β Connection between Compound 8 and Compound 5!
4. AgNOβ Test
Heat with dilute HNOβ + AgNOβ β White precipitate of AgCl
- Confirms organically bound chlorine
5. Hydrolysis
ClCHβCHβCl + 2NaOH(aq) β HOCHβ-CHβOH (Ethylene glycol) + 2NaCl
π Pharmaceutical & Industrial Uses
- Intermediate in synthesis - used to make vinyl chloride (PVC precursor) β
- Solvent - for fats, oils, waxes, resins
- Used to prepare ethylenediamine (pharmaceutical use)
- Grain fumigant (with CClβ) - pest control
- Extraction solvent in laboratory
- Historically used as a topical anaesthetic (applied to skin as cooling agent - evaporates rapidly)
π§ Exam Tips
- IUPAC name = 1,2-Dichloroethane (not 1,1-dichloroethane!)
- Prepared by addition of Clβ to ethylene β
- Reaction with KOH(alcoholic) β vinyl chloride or acetylene (elimination)
- Hydrolysis gives ethylene glycol
- Reaction with NHβ gives ethylenediamine (connects to Compound 5!)
- AgNOβ test gives white precipitate (chlorine test)
- Used as solvent and industrial chemical more than pharmaceutical
ββββ COMPOUND 9: LACTIC ACID
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | 2-Hydroxypropanoic acid |
| Synonyms | Alpha-hydroxypropionic acid, milk acid |
| Molecular Formula | CHβCH(OH)COOH (CβHβOβ) |
| Molecular Weight | 90.08 g/mol |
| Category | Alpha-hydroxy acid (AHA); has chiral centre β |
π§ͺ Structure
OH
|
CHβ -- CH -- COOH
- -COOH (carboxylic acid group)
- -OH (hydroxyl group on alpha carbon)
- CHβ (methyl group)
- Carbon 2 (alpha carbon) is chiral β exists as L- and D- forms ββ
Optical Isomers:
- L-Lactic acid (L(+)-lactic acid) = found in muscle (product of anaerobic glycolysis)
- D-Lactic acid (D(-)-lactic acid) = produced by bacteria (in fermentation)
- DL-Lactic acid = racemic mixture (used in industry)
βοΈ Preparation
Method 1: Fermentation (β Most Important)
Glucose β (Lactic acid bacteria, e.g., Lactobacillus) β 2 Lactic acid
CβHββOβ β 2 CHβCH(OH)COOH
This is anaerobic fermentation (no oxygen needed)
Method 2: From Acetaldehyde (Synthetic)
CHβCHO + HCN β CHβCH(OH)CN (lactonitrile)
CHβCH(OH)CN + HβO/HβΊ β CHβCH(OH)COOH (lactic acid)
Method 3: In Muscles (Biochemical)
Pyruvic acid + NADH β (lactate dehydrogenase) β Lactic acid + NADβΊ
- Occurs during intense exercise (anaerobic glycolysis) β
π¬ Physical Properties
- Appearance: Colourless to pale yellow, viscous (syrupy) liquid β
- Odour: Odourless or faint
- Taste: Sour, acidic taste
- Melting point: 18Β°C (pure L-form); 53Β°C (solid DL-form)
- Solubility: Miscible with water in all proportions; soluble in alcohol; insoluble in chloroform
- pKa: ~3.86 (moderately strong organic acid)
- Hygroscopic: Yes
β‘ Chemical Properties & Reactions
1. Acidic Properties (β)
CHβCH(OH)COOH + NaOH β CHβCH(OH)COONa + HβO (Sodium lactate)
2. Esterification
Lactic acid + Ethanol β Ethyl lactate + HβO (Fischer esterification)
3. Self-Esterification (Lactoyl Lactic Acid)
2 Lactic acid β (condensation) β Lactoyl lactic acid (linear dimer) + HβO
At higher temperatures β Polylactic acid (PLA) - biodegradable plastic!
4. Oxidation
Lactic acid + [O] β Pyruvic acid (CHβCOΒ·COOH) + HβO
- Reverse occurs in metabolism
5. Dehydration
Lactic acid β (heat, -HβO) β Acrylic acid (CHβ=CH-COOH)
6. FeClβ Test
Lactic acid + FeClβ β Yellow colour (distinguishes from other hydroxy acids)
7. Haematin Test / Uffelmann's Test
Lactic acid + FeClβ + phenol β Yellow colour (Uffelmann's test, confirms lactic acid in gastric contents)
π Pharmaceutical Uses (ββ)
- Pharmaceutical solvent and acidulant in formulations
- Buffer solutions (as sodium lactate)
- Ringer's lactate (Lactated Ringer's Solution) - IV fluid for fluid replacement ββ
- Keratolytic agent - in skin preparations (peeling agent)
- Vaginal pH regulator - in vaginal preparations (maintains acidic pH ~3.5-4.5)
- Preservation - in food industry (cheese, yogurt, pickles)
- Dental - calcium lactate for remineralisation
π§ Exam Tips
- Chiral centre = exists as D and L forms ββ (optical isomers!)
- L-Lactic acid = in human muscles (anaerobic exercise)
- Fermentation using Lactobacillus = industrial preparation
- Ringer's Lactate = most important pharmaceutical application ββ
- Uffelmann's test = yellow colour for identification
- Viscous liquid (not solid at room temperature)
- Muscle fatigue/soreness is caused by lactic acid accumulation - clinic connection!
ββββ COMPOUND 10: TARTARIC ACID
π Quick ID
| Feature | Details |
|---|
| IUPAC Name | 2,3-Dihydroxybutanedioic acid |
| Synonyms | Dihydroxysuccinic acid, Racemic acid (DL-form) |
| Molecular Formula | HOOC-CH(OH)-CH(OH)-COOH (CβHβOβ) |
| Molecular Weight | 150.09 g/mol |
| Category | Dihydroxy dicarboxylic acid; has 2 chiral centres ββ |
π§ͺ Structure
COOH
|
HO -- CH
|
HO -- CH
|
COOH
- 2 carboxylic acid groups (-COOH)
- 2 hydroxyl groups (-OH)
- 2 chiral centres (C2 and C3)
Stereoisomers (ββ VERY IMPORTANT)
Because there are 2 chiral centres, tartaric acid has 3 stereoisomers:
| Form | Optical Activity | Notes |
|---|
| L(+)-Tartaric acid | Dextrorotatory (+) | Natural form; found in grapes β |
| D(-)-Tartaric acid | Laevorotatory (-) | Mirror image of L-form |
| meso-Tartaric acid | Optically INACTIVE | Has internal plane of symmetry |
| DL (Racemic)-Tartaric acid | Optically INACTIVE | Equal mix of D and L; called "Racemic acid" β |
- "Racemic acid" was the original name Pasteur used when he discovered optical isomerism - historical fact! β
βοΈ Preparation
-
Natural source: Extracted from argol (crude tartar = potassium hydrogen tartrate deposited in wine barrels) ββ
Argol β dissolved in water β treated with Ca(OH)β β Calcium tartrate β treat with HβSOβ β Tartaric acid
-
Synthetic: From maleic acid via epoxidation and hydrolysis
π¬ Physical Properties
- Appearance: White crystalline solid (colourless crystals)
- Odour: Odourless
- Taste: Strongly sour/acidic taste - β
- Melting point: 168-170Β°C (L-form), 206Β°C (meso-form) β
- Solubility: Freely soluble in water; soluble in alcohol; insoluble in ether
- Optical rotation: L(+)-form rotates plane polarised light to the right
β‘ Chemical Properties & Reactions
1. Acidic Properties (Forms Salts - β Very Important)
Tartaric acid forms 3 types of salts (because it has 2 -COOH groups):
- Cream of tartar = Potassium hydrogen tartrate (KHCβHβOβ) β
- Rochelle salt = Sodium potassium tartrate (KNaCβHβOβΒ·4HβO) β (used in Fehling's solution!)
- Tartar emetic = Antimony potassium tartrate (used as emetic) β
2. Reduction with Zinc/HβSOβ
Tartaric acid β Malic acid β Succinic acid (stepwise reduction)
3. Oxidation
Tartaric acid + HNOβ (conc.) β Oxalic acid + COβ + HβO
4. Heating (Thermal Decomposition)
Tartaric acid β (150Β°C) β Tartronic acid
Tartaric acid β (170Β°C) β Pyruvic acid + COβ
5. Potassium Permanganate Test
Tartaric acid + KMnOβ β Decolourises (reduces KMnOβ) - confirms hydroxyl groups
6. Resorcinol Test (Identification)
Tartaric acid + resorcinol + HβSOβ β Cherry-red colour β
7. Fehling's Test
- Tartaric acid is a component of Fehling's solution B (as Rochelle salt = potassium sodium tartrate) - β this connection is important!
π Pharmaceutical Uses (ββ)
- Acidulant - in effervescent tablets and powders ββ (with sodium bicarbonate)
- Effervescent granules/tablets - tartaric acid + NaHCOβ β COβ bubbles (fizz)
- Tartar emetic (antimony potassium tartrate) - used as emetic and in treatment of schistosomiasis
- Cream of tartar - in baking, and as a stabiliser
- Rochelle salt - component of Fehling's solution (used in glucose testing) β
- Mirror test - Rochelle salt used in Tollens' mirror test calibration
- Chiral resolving agent - resolves racemic mixtures in synthesis β
π§ Exam Tips
- 2 chiral centres β 3 stereoisomers: L(+), D(-), meso ββ
- meso-tartaric acid is optically inactive despite having chiral centres (internal symmetry) ββ
- Natural source: argol (wine barrels) β
- Rochelle salt = component of Fehling's solution β
- Cream of tartar = potassium hydrogen tartrate β
- Resorcinol test = cherry-red colour (identification)
- Used in effervescent preparations with NaHCOβ
π QUICK REVISION TABLE - All 10 Compounds
| # | Compound | Key Feature | Main Use | Identification Test |
|---|
| 1 | Chlorbutol | Tertiary alcohol + 3Cl | Preservative (0.5%) | AgNOβ β white ppt |
| 2 | Dimercaprol | 2 -SH groups; BAL | Heavy metal antidote | Nitroprusside β purple |
| 3 | Glyceryl trinitrate | Explosive nitrate ester | Angina (vasodilator) | FeSOβ β brown ring |
| 4 | Urea | Diamide; 1st organic synthesis | Keratolytic, diuretic | Biuret β violet |
| 5 | Ethylenediamine dihydrate | 2 -NHβ groups | Solubiliser (aminophylline) | Smell of ammonia |
| 6 | Vanillin | -CHO + -OH + -OCHβ | Flavouring agent | FeClβ β blue-green |
| 7 | Paraldehyde | Trimer of acetaldehyde | Status epilepticus | No Tollens' (no free CHO) |
| 8 | Ethylene chloride | Vicinal dihalide | Solvent/intermediate | AgNOβ β white ppt |
| 9 | Lactic acid | 1 chiral centre; AHA | Ringer's lactate | Uffelmann's β yellow |
| 10 | Tartaric acid | 2 chiral centres; 3 isomers | Effervescent tablets | Resorcinol β cherry-red |
π― TOP 10 MOST IMPORTANT EXAM FACTS (KUHS)
- GTN preparation must be below 10Β°C to prevent explosion
- Dimercaprol (BAL) = British Anti-Lewisite - antidote for As, Hg, Pb, Au poisoning
- WΓΆhler (1828) - first organic synthesis from inorganic (urea from NHβCNO)
- Paraldehyde has no free -CHO = negative Tollens' test (but depolymerises to acetaldehyde)
- Tartaric acid has 3 isomers including meso form (optically inactive despite 2 chiral centres)
- Aminophylline = Theophylline + Ethylenediamine
- Lactic acid has 1 chiral centre: L-form in muscles, D-form from bacteria
- Rochelle salt (sodium potassium tartrate) is the component of Fehling's solution
- Vanillin has 3 functional groups: -CHO, -OH (phenol), -OCHβ (ether)
- Chlorbutol preservative concentration = 0.5% in parenteral preparations
Good luck with your exams! π These notes cover everything you need for KUHS PharmD 1st year organic chemistry compounds. Focus especially on Dimercaprol, GTN, Lactic Acid, and Tartaric Acid - they tend to come up most frequently in theory papers. Your complete study notes are ready above! Here's a quick summary of what's included for each compound:
What you get for every compound:
- Chemical name, formula, and structure (drawn out)
- How it's prepared (with equations)
- Physical properties (appearance, smell, solubility, melting point)
- Chemical reactions with examples
- Pharmaceutical uses
- Exam tips highlighted
Priority order for your revision:
π΄ Study first (most exam-important):
- Glyceryl Trinitrate - explosive prep, angina use, mechanism
- Dimercaprol (BAL) - heavy metal antidote, 5-membered chelate ring
- Tartaric acid - 3 stereoisomers, meso form, Rochelle salt
- Lactic acid - chiral centre, Ringer's lactate, fermentation
π‘ Study second:
- Urea - WΓΆhler synthesis (1828), biuret test
- Chlorbutol - preservative 0.5%, camphor smell
- Vanillin - 3 functional groups, FeClβ test
- Paraldehyde - trimer of acetaldehyde, no Tollens' test
π’ Then cover:
- Ethylenediamine dihydrate - aminophylline connection
- Ethylene chloride - vicinal dihalide, synthesis reactions
One tip - for KUHS theory papers, they often ask:
- "Write a note on..." - use the structure + properties + uses sections
- "How is X prepared?" - memorise the preparation equations
- "Identify X" - memorise the identification tests from the quick table at the end
Would you like me to make flashcards, Q&A practice questions, or a downloadable PDF of these notes?