Organic Synthesis

1. Unstable when heated
2. Does not react chemically with other food ingredients
3. Stores well
4. Unlike sucrose, it has no energy value
   1. Calorie free
5. Fahlberg and Remsen
6. High doses → bad health?

1. Discovered accidentally by Sveda
2. Not as sweet as saccharin but does not leave aftertaste
3. Sodium or calcium salt of cyclamic acid
   1. Prepared by sulfonation of cyclohexylamine
      1. Cyclohexylamine it believed to be toxic in animals

1. Dipeptide of phenylalanine and aspartic acid
2. 1965 Schlatter
3. 200 times sweeter than sucrose and dissolves readily in water
4. Tends to interact with other chemicals in food
5. Decomposes hen heated strongly
6. Bacterial Fermentation, Synthesis, Purification

1. Step by Step
2. Consider toxic, hazardous compounds
3. Consider optical isomers: stereo-selectivity

1. % of elements
2. Combustion analysis: % C,H
3. Empirical formula
   1. Mass spectrometer → RMM → Molecular formula

Attachments:

• Organic compounds

1. IR spectroscopy
   1. Functional groups
2. Mass spectrometry
   1. RMM
   2. Ion fragments → possible groups
3. Nuclear Magnetic Resonance (NMR)
   1. Groups of H atoms

1. Isomers
2. Functional group → H bond → ↑ mp/bp

1. Functional group
   1. Electrophiles, neutrophiles
   2. Addition, Sustitution
   3. Oxidation, reduction
2. Acid, base
3. Solubility

1. +: RX reflux with KCN dissolved in ethanol → nitrile, hydrolysis → RCOOH
2. +: Friedel-Crafts alkylation
3. -: Hofmann's degradation (amide + Br2 + KOH + heat → amine)
4. -: Hunsdiecker reaction

1. Starting material, mass production e.t.c.

1. SN1 → racemic mixture
   1. Usually only one enantiomer is useful, the other may be harmful
      1. Thalidomide
   2. Separate and test enantiomers

1. Reduced amounts can be given → less side effects
2. Separate enantiomers
   1. Thin-layer chromatography
   2. £££
3. Asymmetric synthesis
   1. Make only one enantiomer
   2. £££
   3. Extreme condtions
4. Chiral auxillaries
   1. Direct functional groups
   2. Keep costs down
5. Enzymes

1. Still used in treatment of leprosy, cancer

1. Hazcard

1. Control measures to reduce risk

1. Data libraries → drug development