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Organic chemistry: oxygen and nitrogen compounds, polymers and analysis

Alcohols: oxidation (primary → aldehyde → carboxylic acid; secondary → ketone), dehydration, esterification, reaction with sodium; the iodoform test for CH₃CH(OH)–. Phenol: acidity, reactions with bromine water and diazonium salts.

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Hydroxy compounds

Alcohols: oxidation (primary → aldehyde → carboxylic acid; secondary → ketone), dehydration, esterification, reaction with sodium; the iodoform test for CH₃CH(OH)–. Phenol: acidity, reactions with bromine water and diazonium salts.

Carbonyl compounds

Nucleophilic addition with HCN; reduction with NaBH₄; tests with 2,4-DNPH, Tollens' and Fehling's reagents.

Carboxylic acids and derivatives

Acidity and relative strengths (electron-withdrawing groups); acyl chlorides (addition–elimination with water, alcohols, amines); esters (hydrolysis); amides.

Nitrogen compounds

Amines (basicity: alkylamines > ammonia > phenylamine); diazotisation and azo dyes; amino acids (zwitterions, isoelectric point); peptides and proteins.

Polymers

Addition polymers; condensation polymers – polyesters and polyamides (nylon, Kevlar); biodegradability.

Organic synthesis and analysis

Multi-step synthetic routes; chromatography (TLC, GC); infrared spectroscopy (O–H, C=O, N–H); mass spectrometry (M⁺ peak, M+1 for carbon count, fragmentation); carbon-13 and proton NMR (chemical shift, splitting by the n + 1 rule, D₂O exchange).

Worked example: An M⁺ peak has height 30.0 and the M+1 peak 2.0. Estimate the number of carbon atoms.

n = (2.0 ÷ 30.0) × (100 ÷ 1.1) ≈ 6

Exam tip: Combine IR, MS and NMR evidence step by step to deduce a structure.

Check yourself

  1. Why is phenylamine a weaker base than ethylamine?
  2. What does a triplet in proton NMR indicate?
  3. Which reagent reduces aldehydes to primary alcohols?
Show answers
  1. The nitrogen lone pair is delocalised into the benzene ring, making it less available.
  2. The protons have two neighbouring hydrogen atoms (n + 1 = 3).
  3. NaBH₄ (sodium tetrahydridoborate).
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