organic chemistry ii - uoh.edu.sa organic chemicals and multistep synthesis. to practice the...

Download Organic Chemistry II - uoh.edu.sa organic chemicals and multistep synthesis. To practice the fundamentals

Post on 12-Jun-2020

5 views

Category:

Documents

4 download

Embed Size (px)

TRANSCRIPT

  • Organic Chemistry II

    CHEM 202

    Instructor: Prof. Khaled S. Abdel Halim

    k.abdulhalem@uoh.edu.sa http://faculty.uoh.edu.sa/k.abdulhalem/index.html

    UOH Blackboard at www.uoh.edu.sa Lab Sessions/Syllabus

    mailto:k.abdulhalem@uoh.edu.sa http://faculty.uoh.edu.sa/k.abdulhalem/index.html http://www.uoh.edu.sa/

  • Objective: To provide students to the basics of spectroscopic techniques, laboratory synthesis of

    organic chemicals and multistep synthesis. To practice the fundamentals of organic

    spectroscopic equipments such as FTIR and UV-vis. To discuss how HPLC (High

    performance liquid chromatography) is a powerful tool in analysis and how to carry

    experiments on HPLC.

    Outcomes:

    Upon successful completion of this course, students will be able to:

     Understand the principals of organic spectroscopy.

    Practice the identification of organic compounds by FTIR & UV measurements.

    Practice the identification of organic compounds by instrumental analysis.

    Know the fundamentals of HPLC.

     Analyze organic chemistry problems & prepare information and data.

     Demonstrate teamwork skills through assignments tasks.

    Demonstrate communications effectively in oral and written form.

  • 3

    Lab regulations

    Total points: 20 % of the CHEM 202 grade (15 % for lab assignments,

    reports, homework & attendance and 5 % for final lab sheet exam) .

    Safety measures are strictly followed in the lab including: proper clothing

    (pant, shirt and shoes), wearing safety goggles, and shoes.

     Homework problems can be found in the provided manual.

     Homework will be collected on the due date for grading.

    No late homework will be accepted, unless prior arrangements have been

    made with the instructor.

    Comments will be made on solution techniques, and mistakes will be

    indicated.

    Homework

  •  Assignments

    Teams will be formed, with four or five students per group. These groups

    will be used for reporting and presenting on assignments.

    Students are encouraged to work on homework assignments in groups. At

    the end of the semester, each group member may be asked to evaluate (score)

    the other members on contributions to team success.

    All writing assignments will be evaluated on the basis of the quality of the

    communications, as well as on technical content.

    Every assignment will be made to relate the information developed in the

    lab to the real world of organic chemistry. Students will be asked during

    presentations to develop their communications skills.

  • 5

    Lab Reports Each student has to write his own report. A copied report will get zero for the first

    time, and if repeated other actions will be taken including dismissal.

    Lab reports will be graded based on the quality and compliance with the suggested

    format.

    If a student misses a lab without official excuse, he will not be allowed to submit the

    lab report for that lab and he will get zero for that lab.

     Hand plotting is not accepted.

    Safety measures are strictly followed in the lab including: proper clothing (pant, shirt

    and shoes), wearing safety goggles, and shoes.

    Every student should submit his lab report on the due date of the report (one week

    after performing the experiment)

  • 6

    Report Format and Grading:

    Each lab report should include the followings:

    1) Cover Page (title of the experiment, date, student name, instructor name, and

    section number) (1 point)

    2) Introduction and Objectives (background related to the experiment and the

    experiment objectives). (3 points)

    3) Experimental Procedure (brief description of the test procedure and listing the

    main equipment used). (3 points)

    4) Results and Discussion (raw data, observation, example calculation, and evaluation

    of data generated, and good quality graphs). (10 points)

    5) Conclusion (main findings or what the experiment added to your understanding).

    (3 points)

  • Manual Outlines

    This manual will provide an introduction to basic spectroscopic techniques, laboratory

    synthesis of organic chemicals and multistep synthesis. The manual will introduce the

    fundamentals of organic spectroscopic equipments such as FTIR and UV-vis.

    Furthermore, the manual will discuss how HPLC (High performance liquid

    chromatography) is a powerful tool in analysis and how to carry experiments on HPLC.

    Finally, a tutorial for synthesis, purification and identification of organic compounds

    will be introduced. It is important for chemical engineer to have some background in

    organic spectroscopy and organic synthesis tests to understand how dealing with

    different types of organic compounds.

  • Lab. I Fundamental of organic Spectroscopy ……..(Assignment I)

    Lab. II Organic Spectroscopic Problems -(Assignment I Discussions)

    Lab.III FTIR tutorial & polystyrene test …………..............(Report 1)

    Lab.IV UV-vis - Demo & UV – spectrum test…………….(Report 2)

    Lab.V Organic Chemistry problems I

    (Aromatic compounds- Aldehydes& Ketones) ……… HW 1

    Lab. VI HPLC- tutorial………………………………(Assignment II)

    Lab.VII Assignment II Discussions

    Lab.VIII Synthesis of organic compounds- tutorial ......(Assignment III)

    Lab. IX Assignment III Discussions

    Lab.X Organic Chemistry Problems II

    (Carboxylic acids & derivatives- Amines) ….………..HW 2

    Lab XI Organic Chemistry Problems III

    (Biochemistry Problems)……………………………..HW3

  • Lab I: Organic Spectroscopy

    In this part, we shall study the following topics:

     Spectroscopic methods.

     Infrared Spectroscopy.

     Ultraviolet and visible spectra.

  • * Modern spectroscopic methods have largely replaced chemical tests as the standard means of identifying

    chemical structures (particularly in organic chemistry). Spectroscopic techniques are fundamentally based on

    the molecules absorbing energy then monitoring the affect this has on the molecule.

    Overview

    * Spectroscopic methods:

    1. Infrared technique (IR)

    2. Ultraviolet technique (UV)

    3. Mass Spectroscopy

    4. Nuclear Magnetic Resonance

    Electromagnetic Radiation (EMR) : “Visible light is the common type of EMR but this is just a

    small portion of all possible types. Electromagnetic radiation has both particle and wave

    properties

    A particle of energy is called a photon. Each photon has a discrete amount of energy a quantum, ∆E = h ν= h c / λ (h = Planck's constant)

  • Electromagnetic radiation

  • Assignment I

    Design a presentation discussing how organic spectroscopy

    is used in identification of organic compounds?!

  • Lab II: Organic spectroscopy problems

    Suggested approach to solving spectroscopy problems:

    Step 1: Calculate the degree of unsaturation to limit the number of possible structures. The degree of unsaturation indicates

    whether or not the compound has one or more double bonds.

    Step 2: Look at the IR spectrum, especially the region of wavenumbers greater than 1500. Look for likely functional groups,

    working in conjunction with the degree of unsaturation result from Step 1 and with the molecular formula. For instance, if there

    is one double bond and an oxygen, it could be a carbonyl; if there is no double bond and an oxygen, it will be either an ether or

    an alcohol; if there are 4 double bonds, there might be an aromatic ring (and so on).

    Step 3: Study the NMR to determine the connectivity of the compound. Draw the likely functional groups proposed in step 2 and

    see how they might fit together to be consistent with the given NMR spectrum.

    Step 4: Draw a structure consistent with the unsaturation, IR, and NMR data. Check that you have the proper total number of

    carbons, oxygens, hydrogens (and etc.) as consistent with the molecular formula. Check that you have 4 bonds to each carbon.

    Check that the structure you have drawn "fits" with the NMR. If it doesn't, draw another possible structure and check again.

  • Degree of Unsaturation Rule 1: Replace all halogens in the molecular formula by hydrogens. Rule 2: Omit oxygens and sulfurs. Rule 3: For each nitrogen, omit the nitrogen and one hydrogen.

    for the formula CnHm

    Applying these rules to the molecular formula C 8 H

    8 NOBr

    •Rule 1, replace halogens with hydrogens: C8H9NO

    •Rule 2, omit oxygens: C8H9N

    •Rule 3, omit the nitrogen and one hydrogen: C8H8

    Therefore, Dou = 5

    Try with the following compounds: Benzene acetylene ethylene propane

  • Problem 10:

  • Lab III: FTIR spectrometer

    (Polystyrene test)

View more