PHCY256 pKa & FG

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Created by:

gjandrews  on June 2, 2012

Subjects:

chemistry

Description:

Rough acid/base, pKa identification, FG priority.

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PHCY256 pKa & FG

What is the highest priority FG?
Carboxylic acid
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Definitions

What is the highest priority FG? Carboxylic acid
What is the lowest priority FG(excluding a methyl)? Ether
Highest priority between an ester and an amide? Ester
Highest priority between an amide and a nitrile? Amide
Highest priority between an aldehyde and a ketone? Aldehyde
Highest priority between an amine and an alcohol? Alcohol
Highest priority between an amide and an amine? Amide
Highest priority between an amine and a nitrile? Nitrile
Put in order of priority: amine, ketone, nitrile, amide Amide > nitrile > ketone > amine
Put in order of priority: alcohol, ether, amine, ester Ester > alcohol > amine > ether
Put in order of priority: ketone, nitrile, sulfonic acid, aldehyde Sulfonic acid > nitrile > aldehyde > ketone
Benzoic acid, pKa? ~4
Aniline, A/B, pKa? ~5, base
Acetic acid, pKa? ~5
Quinoline, A/B, pKa? ~5, base
Isoquinoline, A/B, pKa? ~5, base
Pyridine, A/B, pKa? ~5, base
Thiophenol, A/B, pKa? ~6.5, acid
Imidazole, A/B, pKa? 7, base
Ammonia, A/B, pKa? ~9, base
Phenol, A/B, pKa? ~10, acid
Dimethylamine, A/B, pKa? ~10, base
Piperidine, A/B, pKa? ~11, base
Ethanol, A/B, pKa? ~15, neutral
Indole, A/B, pKa? ~17, neutral
Pyrrole, A/B, pKa? ~17, neutral
Toluene, A/B, pKa? ~41, neutral
Imine, A/B, pKa? ~5, base
Aromatic amine, A/B, pKa? ~5, base
Amide, A/B, pKa? ~15, neutral
Alcohol A/B, pKa? ~15, acid
Aromatic alcohol, A/B, pKa? ~10, acid
Imide, A/B, pKa? ~8, acidic proton but neutral
Nitrile, A/B, pKa? ~1, neutral (weakly basic)
Sulfonamide, A/B, pKa? ~5, acid
Tetrazole, A/B, pKa? ~5, acid
Sulfonic acid, pKa? ~1
Enol, A/B, pKa? ~5, acid
Amine, A/B, pKa? ~10, base
What is a Claisen-Schmidt reaction? Use of an aromatic aldehyde and an aliphatic aldehyde to create a crossed condensation
What is the Fischer-Speier method? Ester synthesis using carboxylic acid and aliphatic alcohol in acid
What are the two ways of synthesizing esters? Fisher-Speier, and acid chloride/alcohol method
Hemi-acetal synthesis? Carbonyl and primary alcohol, acidic anhydrous conditions
Aldehyde synthesis? Oxidation of primary alcohols in anhydrous conditions
Ketone synthesis? Oxidation of secondary alcohols in anhydrous conditions, or Freidl-Crafts acylation
Carboxylic acid synthesis? Oxidation of primary alcohol with water present
Which part of the ester is named second? The carboxylic acid
What is Williamson synthesis? Use of an alkyl halide to create ethers
What does an aldose reduce to? An alditol
What does HNO3 do to an aldose? Reduces to aldaric acid
What does Br(aq) do to an aldose? Reduces to aldonic acid
What does the enzyme-catalysed reaction produce from aldose? Uronic acid
What aldose reaction results in HOOC-----CH2OH? Oxidation to aldonic acid by Br(aq)
What aldose reaction results in OHC------COOH? Oxidation by enzyme to ironic acid
What aldose reaction results in HOH2C-----CH2OH? Reduction by NaBH4 to an alditol
What aldose reaction results in HOOC------COOH? Reduction by HNO3 to aladric acid
How is an alditol created? Reduction of an aldose by NaBH4
How is an aldonic acid created? Oxidation of an aldose by Br(aq)
How is an aldaric acid created? Oxidation of an aldose by HNO3
How is an urconic acid created? Oxidation of an aldose by enzyme

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