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CHEM 252.09 Organic Chemistry Lab

CHEM 252.09 Organic Chemistry Lab. Name: Dr. Azizeh Farajallah Lab Time: T/ Th 6-9:50 pm AS 1515 Lecture Time: T 6-7 pm AS 1614 Office hours: W,1-2pm & Th 5-6pm Room: IB 2324C Phone: 934-3940 Email: azizeh.farajallah@seattlecolleges.edu. Learning Objectives.

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CHEM 252.09 Organic Chemistry Lab

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  1. CHEM 252.09Organic Chemistry Lab Name: Dr. AzizehFarajallah Lab Time: T/Th 6-9:50 pm AS 1515 Lecture Time: T 6-7 pm AS 1614 Office hours: W,1-2pm & Th 5-6pm Room: IB 2324C Phone: 934-3940 Email: azizeh.farajallah@seattlecolleges.edu

  2. Learning Objectives • Study the properties, reactions and synthesis of representative classes of organic compounds • Introduction to research techniques by way of independent projects • Introduction to qualitative organic analysis (unknown analysis).

  3. How to succeed • Prelab ( in your notebook and turn in photocopy) 5-10 pts • No make up labs • Follow safety guidelines • Experiment/lab report, 20-35 pts • Exam, 100 pts • Notebook/instructor evaluation, 50 pts

  4. Food Goggles Eyewash station Foot wears

  5. Fire Extinguisher Personal Items The safety shower Fire Alarm

  6. Azo Compounds • Contain the -N=N- group. • Azo group is stabilised by becoming part of extended delocalised system. R-N=N-R' Azo group Butter Yellow/methyl yellow

  7. Color Color rises when a molecule absorbs certain wavelengths of visible light and transmits or reflects others

  8. Chromophor • It is the part of a molecule responsible for its color • When visible light hits the chromophore/absorbed exciting an electron from its ground state into an excited state.

  9. Auxochrome An auxochrome is a functional group of which, when attached to a chromophore, alters both the wavelength and intensity of absorption. Methyl orange

  10. Diazonium Ion + HNO2(aq) + HCl(aq) **ONLY POSSIBLE WITH AROMATIC (ARYL) AMINES (BECAUSE OF DELOCALISATION OF ELECTRONS LEADING TO STABILISATION)** ∆ ≤ 5oC Benzendiazonium chloride Nitrous acid is unstable, so made in situ NaNO2(aq) + HCl(aq)NaCl(aq) + HNO2(aq)

  11. Diazonium Ion + HNO2(aq) + HCl(aq) **The reactions of a diazonium salt are always done with a freshly prepared solution. Diazonium salts are unstable and tend to be explosive as solids.)** ∆ ≤ 5oC Benzendiazonium chloride Water is a side product, if heated a nucleophilic substitution formation phenol and nitrogen gas

  12. Coupling Reaction Electrophilic Attack ATTACK AT PARA POSITION, UNLESS ALREADY TAKEN

  13. Mechanism

  14. USES • Synthetic dyes, especially in the clothing and fashion industry • pH Indicators; Methyl orange frequently used in acid titrations

  15. Concerns Concern over the possible carcinogenicity of some azo compounds; Butter Yellow, was once used as a food coloring Butter Yellow methyl yellow

  16. The Synthesis, Purification, and Characterization of Ferrocene

  17. Background of Ferrocene • “Accidental” Discovery (A. Kealy and Pauson – 1951) 2C5H5MgBr + FeCl2 C5H5FeC5H5 + MgBr2 + MgCl2 Pauson and Kealy's original (incorrect) notion of ferrocene's molecular structure

  18. Background • Lead to Development and Research in Organo-metallic Chemistry • Earliest and Best Known of the “Sandwich” Compounds

  19. Background •  In 1973 Fischer of the Technische Universitat Munchen and Wilkinson of Imperial College London shared a Nobel Prize for their work on metallocenes and other aspects of organometallic chemistry.

  20. Ferrocene Acetylation

  21. Purification/characterization • Extraction • TLC • Column chromatography • Melting point/NMR 125-127°C 81-83°C

  22. Ferrocene Application • Fuel additive to promote smokeless combustion • Exhibit anticancer activity • Scientists succeeded in altering carbon nanotubes so that they supply electrons when exposed to light.  Ferrocene is known for its tendency to relinquish electrons

  23. Lab Check in • X drawers • Lock combination • Check your glassware/fill our the check in sheet • Sign the safety sheet

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