Oxygen Bearing Compounds

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3/5/2011

EXPERIMENT

EXPERIMENT

8
OBJECTIVES CONCEPTS REAGENTS PROCEDURE RESULTS DISCUSSION IR ANALYSIS

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Objectives
to differentiate various types of oxygen-bearing organic compounds to device a scheme to distinguish each functional group

Analysis of Oxygen-bearing Organic Compounds
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OBJECTIVES CONCEPTS REAGENTS PROCEDURE RESULTS DISCUSSION IR ANALYSIS

to characterize an unknown sample through parallel chemical tests

ARMSALCEDO

ARMSALCEDO

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EXPERIMENT

EXPERIMENT

8
OBJECTIVES CONCEPTS REAGENTS PROCEDURE RESULTS DISCUSSION

Reagents
OH

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OBJECTIVES

Reagents
Chemical Analysis
Anhydrous ZnCl2 10% KI 10% K2Cr2O7 6M H2SO4 6M 6M NaOH conc. HCl DNPH reagent Tollen’s reagent 5% aq. NaClO

OH
CONCEPTS

HO
1° alcohol 2° alcohol 3° alcohol

REAGENTS PROCEDURE

O

O

RESULTS DISCUSSION

H
IR ANALYSIS

H
Ketone
IR ANALYSIS

Aldehyde

ARMSALCEDO

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EXPERIMENT

EXPERIMENT

8
OBJECTIVES CONCEPTS REAGENTS PROCEDURE RESULTS DISCUSSION SUMMARY

Procedure
Schematic Analysis
Sample Dichromate test Green soln Yes 1°/2° alcohols, aldehyde Tollen’s test Silver mirror Yes Aldehyde No 1°/2° alcohols Lucas test No 3°/ketone DNPH test Orange ppt Yes Ketone No 3° alcohol

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OBJECTIVES CONCEPTS REAGENTS PROCEDURE RESULTS DISCUSSION IR ANALYSIS Turbid fast Yes 2° alcohol alanx3@yahoo.com
ARMSALCEDO

Discussion
Dichromate Test (Jones oxidation)
REAGENTS: 10% K2Cr2O7, 6M H2SO4 POSITIVE FOR: 1 and 2 alcohols, aldehydes POSITIVE RESULT: green to blue solution REACTION: R OH R K2Cr2O7 H2SO4 R R O + 6H2O + Cr2(SO4)3 green

No

1° alcohol

ARMSALCEDO

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1

3/5/2011

EXPERIMENT

EXPERIMENT

8
OBJECTIVES CONCEPTS REAGENTS PROCEDURE RESULTS DISCUSSION IR ANALYSIS

Discussion
Tollen’s Test
REAGENTS: 1% AgNO3, 6M NaOH, conc. NH4OH POSITIVE FOR: aldehydes POSITIVE RESULT: silver deposits (mirror) REACTION: O H R + 2Ag(NH3)2+OHR O O-NH4+ + 2Ag + silver deposits 3NH3 + H2O

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OBJECTIVES CONCEPTS REAGENTS PROCEDURE RESULTS DISCUSSION

Discussion
DNPH Test
REAGENTS: 2,4-dinitrophenylhydrazine solution POSITIVE FOR: aldehydes, ketones POSITIVE RESULT: yellow or red-orange precipitate REACTION: R HN NH2 O HN N R R R O2 N O2 N NO2 NO2

IR ANALYSIS

ARMSALCEDO

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ARMSALCEDO

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EXPERIMENT

EXPERIMENT

8
OBJECTIVES CONCEPTS REAGENTS PROCEDURE RESULTS DISCUSSION IR ANALYSIS

Discussion
Iodoform Test
REAGENTS: 10% KI, NaClO POSITIVE FOR: methyl ketones POSITIVE RESULT: yellow precipitate REACTION: O CH3 R 3I2 4NaOH R 3H2O CHI3 (s) yellow O O-Na+ 3NaI

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OBJECTIVES CONCEPTS REAGENTS PROCEDURE RESULTS DISCUSSION

Discussion
Lucas Test
REAGENTS: conc. HCl, ZnCl2 POSITIVE FOR: 2 and 3 alcohols POSITIVE RESULT: cloudy or turbid solution REACTION: R R' OH R'' + HCl ZnCl2 R' R'' R Cl + H2O

IR ANALYSIS

ARMSALCEDO

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ARMSALCEDO

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EXPERIMENT

8
OBJECTIVES CONCEPTS REAGENTS PROCEDURE

Summary
TESTS REAGENTS K2Cr2O7 H2SO4 AgNO3, NaOH, NH4OH 2,4dinitrophenylhydrazine KI, NaClO POSITIVE FOR 1° and 2° alcohols aldehydes aldehydes VISIBLE RESULT Green solution

Dichromate

Tollen’s

silver deposits (mirror) Red-orange precipitate yellow precipitate cloudy or turbid solution

DNPH
RESULTS DISCUSSION IR ANALYSIS

ketones

Iodoform

methyl ketones 2° and 3° alcohols

Lucas

HCl, ZnCl2

ARMSALCEDO

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