1 - AROMATICS (PHENOLS)
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what is the structure of phenol?
what is the pKa of phenol?
10 phenol is a weak acid
what are some uses of phenol?
• used to sterilize surgical instruments and clean wounds (it is an antiseptic) • can be used as an analgesic to relieve minor pain • corrosive, can cause severe chemical burns • at low concentrations used to do chemical peels on the skin • rubber, dyer, perfumes, ink, plastic and epoxy resin (through reactions)
structure of BHT (butylated hydroxy toluene) and function
antioxidant food additive
structure of salicylic acid and aspirin
structure of vanillin and function
flavoring agent
where can vanillin like fragments be found?
in lignin natural constituent of wood, present in cell walls
what are the different methyl phenols used for (o,m or p)
constituents of cresote, from coal tar or crude oil used in disinfectants, deodorizers and insecticides
what are benzene diols used for?
film developing agent disinfectant reducing agent, film developing, skin whitening agent
what are ways in which phenols can be identified?
• ferric chloride color test the solution turns purple when there is phenol prosent the iron makes a complex with the phenols • in IR, there is the characteristic 3600cm^-1 broad curved stretch, with some interference from the intermolecular H bonding • through NMR spectroscopy
what are the pKas of alcohols?
16-18 phenol is a stronger acid than other alcohols
why is phenol more acidic that other alcohols?
• resonance effect: the phenoxide negative charge can be delocalised throughout the ring, which leads to a more stable conjugate base = more acidic • orbital and inductive effects: aliphatic alcohols are bound to an sp3 carbon, while on phenol the carbon is sp2 this increases the s character, and makes it was electron withdrawing, which again leads to greater stabilization
what is the pKa of carboxylic acids?
4-5
what are the different solubilities of carboxylic acids, phenols and alcohols in strong vs weak bases?
carboxylic acids: soluble in both phenols: soluble in strong but not in weak alcohols: soluble in neither
what is NaNO2 and HCl a source of?
source of nitrosonium ion (Ntriple bond O+)
synthesis of phenol from nitrobenzene
how is nitrosonium ion formed?
mechanism from aniline to diazonium salt derivative
