Identify an Unknown
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Transcript of Identify an Unknown
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Type of compound:
Aldehyde
Alcohol
Amine
Ketone
Identify an Unknown
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1. Physical PropertiesMelting point or boiling point
2. Functional Group
Infrared spectrum
NMR Spectrum
Solubility
Classification Tests
3. Solid Derivative
Procedure
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Distill your unknown and note the boiling point
If can’t distill or not enough sample use this technique.
Measure boiling point of liquids
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Carbonyl Group (1650 - 1725 cm-1)?
Yes No
Aldehyde Ketone
NMR
Aldehyde Ketone
+ -
Alcohol Amine
Broad OH in IR
Yes NoAlcohol Amine
(Basic?)3700 - 4000 cm-1
Yes
Primary or Secondary
No
Tertiary
Functional Group
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NH2NH
NO2
NO2
Aldehyde or ketone
2,4-dinitrophenylhydrazine test
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+ NH2NH
NO2
NO2
2,4-dinitrophenylhydrazone
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C
O
NH2R C
OH
NHR
NRC
DNP Mechanism
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Reagent: NaOH and I2 (NaOI)
CCH3
O
RI2, NaOH
RCOOH + CHI3Yellow
Iodoform Test
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CCH3
O
RI2, NaOH
RCOOH + CHI3Yellow
CHCH3
OH
RI2, NaOH
RCOOH + CHI3Yellow
Iodoform Test
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Iodoform Test
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(NH4)2Ce(NO3)6 + ROH
(NH4)2Ce(NO3)5OR
+ HNO3
Ceric Nitrate Test for Alcohols
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1. Odor
2. If not soluble in water they may dissolve in dilute aqueous acid (HCl).
3. Water solutions of amines are basic to litmus.
Amines
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SO2Cl
Benzenesulfonyl Chloride
Hinsberg Test for Amines
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Primary: Soluble. PPT if add HCl
Secondary: Insoluble
Tertiary: Tends not to react
Hinsberg Test for Amines
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Aldehydes and Ketones
1. 2,4-dinitrophenylhydrazone
2. Semicarbazone
NH2NHC
O
NH2
semicarbazide
+ RC
O
R NNHCNH2CR
R
O
semicarbazone
Derivatives
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O2N
O2N
C Cl
O
O2N
O2N
C OR
OROH
3,5-dinitrobenzoyl chloride
3,5-dinitrobenzoate
Alcohol Derivative
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Primary and Secondary Amines
C
O
Cl + RNH2 C
O
NHR
Benzoyl Chloride Benzamide
SO2Cl + RNH2 SO2NHR
Benzenesulfonyl Chloride Benzenesulfamide
Amine Derivatives
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B.p. =198-200o
DNP = 231-235o
Sample Unknown
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Table
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Structure of Unknown
C
O
CH3
acetophenone
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Sample Unknown
B.p. = 80 - 85o
3,5-dinitrobenzoate = 119 - 121o
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CCH3 CH3
H
OH
isopropyl alcohol
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B.p = 106o
3,5-dinitrobenzoate 85o
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CH2OHCH
CH3
CH3
isobutyl alcohol
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B.p. = 160o
3,5-dinitrobenzoate: 108-110o
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OH
H
cyclohexanol
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B.p. = 155-157o
2,4-DNP = 158 - 160o
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O
cyclohexanone
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B.p. = 180 -183o
Benzenesulfonamide 110 - 112o
Benzamide 160 - 163o
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NH2
aniline