Functional groups of oxygen 5 1) alcohols phenols ethanol phenol ethanal dimethyl ketone 3) aldehydes ketones dodecanoic acid ethanoic acid
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Functional Groups
1Chemistry and Introduction to Biochemistry
F Malatesta
2 download it http://avogadro.cc/Avogadro is an open source advanced molecule editor and visualizer designed for cross-platform use in computational chemistry, molecular modeling, bioinformatics, materials science, and related areas. It offers flexible high quality rendering and a powerful plugin architecture.
3A functional group is defined as a part of the structure of a molecule characterized by specific elements, which gives the compound a typical reactivity similar to that of other compounds containing the same group. In other words, the functional group constitutes the center of the chemical reactivity of the molecule.
Functional Groups Chemistry and Introduction to Biochemistry functional group class of compounds notescarbon-carbon double bond alkenes carbon-carbon triple bond alkynes any halogen • haloalkanes • acyl halides • when it substitutes an H in an alkane • when it substitutes an OH in a carboxylic acid hydroxy • alcohols • enols • phenols • when bound to sp
3 carbon • when bound to sp 2 carbon • when bound to an aromatic ring sufyhydryl thiols when bound to sp 3 carbonaldehyde aldehydes carbonyl ketones carboxylic carboxylic acids amine • amines • aromatic amines • ammides • when it substitutes an H in an alkane • when bound to an aromatic ring • when it substitutes an OH in a carboxylic acid 4
Functional groups of oxygen
51) alcohols & phenols
ethanol phenol ethanal dimethyl ketone3) aldehydes & ketones
dodecanoic acid ethanoic acid4) carboxylic acids 2) ethers
dimethyl etherAlcohols and phenols
The functional groups of oxygen are numerous and important. The simplest is the hydroxyl group:Nomenclature: the name of an alcohol is given by the name of the corresponding hydrocarbon, to which the ending -ol is added. The longest hydrocarbon chain is identified, and is numbered by giving the lowest number to the C to which the OH is bound.
2-methyl-1-propanol 2-methyl-2-propanol 3-bromo-3-methylcyclohexanol 2-butanol
6Some alcohols
Alcohols are Found in Many Natural Products
9An alcohol can be viewed as either a hydroxyl derivative of an alkane or an alkyl derivative of water
ethane ethyl alcohol (ethanol) water 10 11The presence of the OH group makes alcohols polar, therefore soluble in water, and it raises the boiling point with respect to the corresponding alkanes.
alcohol solubility in H 2O at 25 °C methanol miscible ethanol miscible 1-propanol miscible 2-methyl-2-propanol miscible 2-methyl-1-propanol 10% 1-butanol 9.1% 1-pentanol 2.7% cyclohexanol 3.6% 1-hexanol 0.6% phenol 9.3% alkane T
eb (°C) alcohol T eb (°C) CH 4 3OH 64.8 CH
3 CH 3 3 CH 2 OH78.3 CH
3 CH 2 CH 3 3 CH 2 CH 2 OH 97.112
Compounds containing 2 (3) OH groups: diols (triols) propane-1,2,3-triol (glycerol) → lipids hexane-1,6-diol ethane-1,2-diol (glicole etilenico) propane-1,2-diol (glicole propilenico)
13primary tertiary secondary Alcohols are also classified according to the carbon the hydroxyl is directly attached to:
14Acid-base reactions
Alcohols have only weak acidic character (methanol andethanol about as water, others with longer chain even less) and do not react with weak bases. It is therefore necessary to use very strong bases (e.g. sodium hydride)
ROH + NaH → RO
Na + H 2 CH 3 CH 2OH + NaH → CH
3 CH 2 O Na + H 2 15In the absence of electron-withdrawing groups (which increase their acidity) and electron-repelling groups (which reduce their acidity) the ionization constants are ca. K
A = 1 10 -15 MAlcohols are very weak acids
CH 3OH + H
2O CH
3 O + H 3 OAlthough they have a hydroxyl group (-OH), the phenols do not behave like alcohols. Phenol has a weak acidic character: pK
A = 9.95 16This happens because the negative charge of the anion that is formed by the dissociation of the hydrogen of the hydroxyl group (phenate ion) is stabilized by resonance on the whole aromatic ring.
17