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The structure and nomenclature of alcohols, ethers and epoxy compounds Part 1

 GCE-AS-A2-IB ADVANCED LEVEL ORGANIC CHEMISTRY

Examples of displayed formula, graphic formula, molecular formula, skeletal formula, structural formula

1a Open chain single OH alcohols and ethers 1b chloroalcohols

2. diols-triols * 3. cyclo-alcohols * 4. phenols * 5. epoxyalkanes

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• Diol and triol structures are named on the basis of the longest carbon chain and the suffix 'ol'.
• Diol and triol means two or three hydroxy groups in the molecule.
• The positions of the OH groups is denoted with the lowest possible numbers.
• The prefix uses the full parent alkane name e.g. butane….

1. Ethane-1,2-diol (ethylene glycol, glycol), ,
2. Propane-1,2-diol , ,
3. Propane-1,3-diol , ,
4. Propane-1,2,3-triol (glycerol), ,
5. Butane-1,2-diol , ,
6. Butane-1,3-diol , ,
7. Butane-1,4-diol , ,
8. Butane-2,3-diol , ,
9. Butane-1,2,3-triol , ,
10. Butane-1,2,4-triol , ,
11. Pentane-1,2-diol ,   ,
12. Pentane-1,3-diol ,   ,
13. Pentane-1,4-diol ,   ,
14. Pentane-1,5-diol ,   ,
15. Pentane-2,3-diol ,   ,
16. Pentane-2,4-diol ,   ,
17. Hexane-2,3-diol , ,
18. Hexane-2,5-diol , ,

• Cycloalcohols (cycloalkanols) are named on the basis of the number of carbon atoms in the ring (minimum 3) and the prefix 'cyclo' and the suffix 'ol'
• The prefix alkane name e.g. 'prop' has an 'a' added but leaves out the end 'ne' if more than one OH group (note in mono-hydroxy alcohols its propan… and in diols/triols etc. it is propane…)

1. Cyclopropanol (cyclopropyl alcohol), ,
2. Cyclobutanol (cyclobutyl alcohol), ,
3. Cyclopentanol (cyclopentyl alcohol), ,
4. Cyclopentane-1,2-diol , ,
5. Cyclopentane-1,3-diol , ,
6. Cyclohexanol (cyclopropyl alcohol), ,
7. Cyclohexa-1,2-diol , ,
8. Cyclohexane-1,3-diol , ,
9. Cyclohexane-1,4-diol , ,
10. Cyclohexane-1,2,3-triol , ,
11. Cyclohexane-1,2,4-triol , ,
12. Cyclohexane-1,3,5-triol , ,

If the OH group (hydroxy) is directly attached to a benzene ring, the molecule is classified as a 'phenol'. If not, the molecule is classified as an aliphatic alcohol (e.g. all the previous examples so far!). This difference is illustrated below with molecules containing a benzene ring.

1. phenols: phenol, 2-chlorophenol, 2-hydroxybenzoic acid,
   • 2-hydoxyphenylethanone,  methyl 2-hydoxybenzoate,
     • all have an OH group attached directly to a benzene ring.
2. and these can be classified as aliphatic alcohols:
3. phenylmethanol (benzyl alcohol),
   • which is isomeric with the ether, methoxybenzene (anisole)
4. 1-phenylethanol,
   • which is isomeric with the ether, ethoxybenzene (phenetole)

5. Examples of epoxy-alkane structures and names

• Epoxy compounds have a -C-C-O- triangle (epoxide/oxirane ring)in their structure which is equivalent to the simplest cyclic ether but much more reactive because of the C-O-C or O-C-C bond angle strain (60^o instead of 109^o in ethers like ethoxyethane) e.g.

• epoxyethane (ethylene oxide)

• epoxypropane (propylene oxide)

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