Beruflich Dokumente
Kultur Dokumente
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Polarity Saturated compounds,
hydrocarbons, aromatics
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- Description of the distribution of charges within a Neutral/very weak base
eH w
molecule N H2SO4 forced protonation
o.
Oxygen-containing
Organic rs e
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compound Class S
- Water-soluble compounds
o Limited: 5 carbons or less per H-bonding
insoluble+
o
soluble + group
diethyl ether
aC s
o ROH alcohol
o RC=OOH carboxylic acid
S2 S1 insoluble + soluble + o RNH2 amine
5% HCl 5% NaHCO3 o RC=ONH2 amide
o RC=O carbonyl
ed d
o ROR ester
ar stu
B A2 A1
insoluble S1 S2
Polar Highly polar
sh is
M I N Class A
- NaOH-soluble compounds
- Acidic groups:
o R=COOH carboxylic acids
o Ar-OH phenols (rel. weaker)
A1 A2
Strongly acidic Weakly acidic
NaHCO3 soluble Insoluble
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Class B o Single solvent + water
o Mixed solvent + water + ethanol
- HCl-soluble
2. Heat
- Basic groups
3. Charcoal (very small amount)
o RNH2 amine
o Adsorption of colored impurities
Class M 4. Hot filtration
o Avoid premature recrystallization
- Have N – not basic
(↓ %recovery)
- Have S – not acidic
Fluted filter paper
- Groups
Short-stemmed funnel
o RC=ONH2 amide
Pre-heated receiving flask (or w/
o R-NO2 nitro
hot water)
Class N 5. Cool to room temperature
o Slow cooling – allow particle growth
- Conc. H2SO4-soluble
o Large crystals
- Neutral/very weak bases (benzaldehyde, benzyl
High filterability
alcohol)
↑ %purity – less SA exposed
- Forced protonation salt + water
6. Filter + wash crystals
- N/S/O-containing compounds
o Cold solvent – prevent redissolution
- Unsaturated compounds (electron-rich)
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er as
- ROH + H2SO4 ⇄ ROH2 + HSO4-
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PARAMETER RECRYSTALLIZATION SUBLIMATION
RC=O + H2SO4 ⇄ RC=OH+R + HSO4-
eH w
-
- RC≡N + H2SO4 ⇄ RC≡NH+ + HSO4- Procedure Tedious Simple and easy
o.
Class I Many steps Single step,
rs e
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- Insoluble in all no solvent
- Saturated compounds, aromatics, alkyl halides
% yield High Low
% purity Low High
o
m
- SP: water adsorbed on cellulose
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o Conformational
- MP: solvent (via capillary action) Free rotation about a single bond
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giving rise to different isomers
eH w
Solvent
Torsional strain
- Moderately volatile Eclipsing
o.
- Good resolving power – no tailing
- Non-toxic rs e Steric strain
Bulky groups
ou urc
- Cheap o Geometric (cis-trans) isomers
Chromatographic chamber Restricted rotation about a double
bond or a ring structure
o
Same group
- Paper should not touch the sides of the chamber
vi y re
E-Z
- Unimpeded uniform rise of the MP Different groups
- Solute sample – (prioritized)
o Not below the solvent level
Cahn-Ingold-Prelog rules
o Just enough (too much will leave a tail, too
ed d
o Optical
little will not show spots)
Not superimposable
ar stu
- Slow rise of MP
Can rotate plane-polarized light
o Open chamber
Optically active chiral
o Thick paper
Enantiomers
Spot detection Mirror images
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Not superimposable
- Under visible light
Th
Diastereomers
- Iodine chamber detect unsaturated compounds
Non-mirror images
Retention factor Not superimposable
- Good resolution: Rf = 0.4 – 0.8 Meso copounds
Superimposable
𝑑𝑖𝑠𝑡𝑎𝑛𝑐𝑒 𝑡𝑟𝑎𝑣𝑒𝑙𝑒𝑑 𝑏𝑦 𝑠𝑜𝑙𝑢𝑡𝑒 Identical
𝑅𝑓 =
𝑑𝑖𝑠𝑡𝑎𝑛𝑐𝑒 𝑡𝑟𝑎𝑣𝑒𝑙𝑒𝑑 𝑏𝑦 𝑠𝑜𝑙𝑣𝑒𝑛𝑡 Optically inactive
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E6: PREPARATION AND PURIFICATION OF AN ALKYL HALIDE More accurate
o Continuous flow of water
- Nucleophilic substitution reaction
Condensation is maximized
SN1 SN2 o Sealed joints
Prevent volatilization
Unimolecular Bimolecular
Two steps One step
E7: ALCOHOLS, PHENOLS, AND ETHERS
3° > 2° > 1° > CH3 CH3 > 1° > 2° > 3°
Lucas Baeyer’s
R R+S RS
Ethanol None after 10m Brown ppt,
Non-stereospecific Stereospecific decolorization
Rate = k[RX] Rate = k[RX][Nu-] Isopropyl alcohol 5m Brown ppt,
decolorization
Electrophile (E+) Nucleophile (N-) Leaving groups Benzyl alcohol Immediately Brown ppt,
decolorization
Electronegative Large/↑ # of e- Stable
m
Diethyl ether Purple solution
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EWG ↑ polarizability Weak base
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(NH3/H2O
eH w
Halides Lucas Test
o.
t-BuOH HCl OH (strong base) - Differentiate 1°, 2°, 3° alcohols
- Secondary ketones
o Salt-out agent - ↑ polarity of aqueous layer, - Ethers –
more distinct layers o do not decolorize
3. Organic layer + solid NaHCO3 o Inert to oxidation by MnO4-
o Neutralize excess HCl - Phenol Ketone
o Aqueous NaHCO3 – introduce water
o Effervescence – indicator of the pH FeCl3 Br2 in H2O KMnO4
neutralization reaction
Phenol 5 Violet White Brown ppt
4. Filtrate + CaCl2
o Remove water formed and excess alcohol p-nitro 3 Red
o Prevent hydrolysis
Picric 1
5. Simple distillation
o Boiling chips Β-naphthol Green
Distribute heat evenly
p-bromo Yellow
Prevent superheating
o Vapor temperature measured (not liquid’s)
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Acidity of phenols Hexane Limonene Benzene
- Electron withdrawing groups more acidic State Liquid Liquid liquid
Bromination of phenols Color Colorless Yellow Colorless
- Br2 in H2O (Lewis acid) H2O Insoluble Insoluble Insoluble
- E+AS
Density Less dense Less dense Less dense
FeCl3
T-BuCl/AlCl3 Yellow Yellow Orange
- Complexation [R3Fe] (FC’s crystals crystals crystals
alkylation)
Br2, light Colorless Colorless Smoky
E8: ALIPHATIC AND AROMATIC HYDROCARBONS
(FRS) yellow
Alkanes
Br2, dark Red orange Colorless Red orange
- Inert
KMnO4 Purple Brown ppt, Purple
- Free radical reactions – require light/heat
solution decolorization solution
Alkenes/alkynes
Combustion Blue, Yellow, Yellow,
m
- Loosely held pi electrons reactive
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non-smoky non-smoky smoky
- Reactivity: alkenes > alkynes
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- Electrophilic addition reactions
eH w
Aromatics E9: RELATIVE RATES OF ELECTROPHILIC AROMATIC
o.
- Special stability due to resonance SUBSTITUTION
-
rs e
Electrophilic aromatic substitution ELECTRON DONATING (o,p)
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- Huckel’s rule
o # of pi electrons = 4n + 2 Strong -OH
-NH
Distillation -NHR
o
-COOR
- Br2, light/dark + brown to colorless -CHO
o Light – alkanes (FRS) -COR
o Dark – alkenes, alkynes (E+A) -CONH2
- Alkylation + orange crystals -SO3H
o Aromatic compounds Strong -NO2
- Baeyer’s/KMnO4 + decolorization, red ppt -NR3+
o Unsaturated compounds, phenols, 1°/2° OH -CX3
- Combustion
o Higher C:H ratio and heat resistance – C
released as soot
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