Unsaturation, alcohols, phenols and acids4 concepts
| Compound | Bromine water fades | How (from the structure) | Precipitate |
|---|---|---|---|
| hex-1-ene | ✓ | addition (C=C) | none |
| phenol | ✓ | substitution | white ppt |
| aniline | ✓ | substitution | white ppt |
| benzene | ✗ | : | : |
| cyclohexane | ✗ | : | : |
- Not proof of a C=C when bromine water fades. Phenols and aniline also use up bromine, but by substitution, giving a white precipitate and HBr. Addition to an alkene gives no precipitate.
| Compound | Class (from structure) | CAN | Lucas |
|---|---|---|---|
| ethanol | 1° | red | clear at room temp. |
| propan-2-ol | 2° | red | about 5 min |
| 2-methylpropan-2-ol | 3° | red | turbid at once |
| benzyl alcohol | 1°, benzylic | red | turbid at once |
| phenol | phenol (ring C–O) | : | no reaction |
- Lucas turbidity is the insoluble RCl; its speed follows carbocation stability, so benzyl and allyl alcohols react at once like 3°. Phenols do not react, as the ring C–O bond does not break.
- Na metal frees from a dry alcohol, but it is not specific: water, phenols and acids also give .
| Acid | C=C (from structure) | Neutral FeCl₃ | Bromine water |
|---|---|---|---|
| benzoic acid | ✗ | buff ppt | no change |
| cinnamic acid | ✓ | buff ppt | decolourised |
- Bromine water gives a white precipitate of 2,4,6-tribromophenol at once, with no catalyst. Phthalein dye test: heat with phthalic anhydride and conc. , then add NaOH; phenolphthalein shows pink-red.
- Not only phenols colour neutral . Acetate gives a deep red colour and benzoate a buff precipitate. So cannot tell benzoic acid from cinnamic acid; bromine water can (cinnamic acid's C=C).
| Compound | Dissolves in NaOH | NaHCO₃ fizzes |
|---|---|---|
| ethanoic acid | ✓ | ✓ |
| phenol | ✓ | ✗ |
| picric acid | ✓ | ✓ |
| benzenesulphonic acid | ✓ | ✓ |
| benzyl alcohol | ✗ | ✗ |
| 4-(dimethylamino)phenol | ✓ | ✗ |
- Not every –OH dissolves in NaOH. Only an acidic one: a ring –OH (phenol), –COOH or ; is an alcohol and stays out. A ring –OH still dissolves when the ring also carries .
- Not a carboxyl test for every 'acid'. Sulphanilic acid is a sulphonic acid with no –COOH, so it gives no ester test, though its N and S do show up in Lassaigne's test.
- Not always –COOH when fizzes. Any acid stronger than gives . Phenol does not, but picric acid (2,4,6-trinitrophenol) and sulphonic acids do.
- Quick method. In a separating funnel, aqueous NaOH pulls only acids (as salts) into water; amines need dilute HCl, and neutral compounds never move. Benzoic acid leaves ethyl acetate; aniline and chlorobenzene stay.
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14 more concepts in 6 topics
Aldehydes and ketones, Amines, Syllabus preparations, Titrimetric analysis and Physical experiments (NTA list), plus ideas from Purification, Mole concept. Read the first part free. Sign in free with Google to read the rest and download the PDF.
Aldehydes and ketones3 concepts
- 2,4-DNP test: any aldehyde or ketone2×
- Tollens', Fehling's, Benedict's, Schiff's7×
- Iodoform test and preparation2×
Amines3 concepts
- Carbylamine test: 1° amines only3×
- Hinsberg test: 1°, 2° or 3°1×
- Nitrous acid and the azo-dye test1×
Syllabus preparations3 concepts
- Acetanilide and p-nitroacetanilide1×
- Aniline yellow (p-aminoazobenzene)
- Mohr's salt and potash alum
Titrimetric analysis3 concepts
- Primary standards4×
- Acid–base indicators5×
- KMnO₄ vs oxalic acid and Mohr's salt2×
Physical experiments (NTA list)2 concepts
- Enthalpy of solution and neutralisation
- Sols and the iodide–peroxide clock
Also asked here: Purification, Mole concept
- Key points1
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