211 PHC By: Dr. Reem Al-Wabli Dr. Ebtehal Al-Abdullah Dr. Maha Al-Mutairi.
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Transcript of 211 PHC By: Dr. Reem Al-Wabli Dr. Ebtehal Al-Abdullah Dr. Maha Al-Mutairi.
211 PHC
By:Dr. Reem Al-WabliDr. Ebtehal Al-AbdullahDr. Maha Al-Mutairi
Dr. Reem Al-WabliAssistant Professor in Pharmaceutical
Chemistry Department
Office no. S69(67)
Course Evaluation
Total(Marks)
Final (Marks)
Activities (Marks)
Midterms (Marks)
15 - 5 Midterm I(10)
Dr. Reem
30 15 5 Midterm II(10)
Dr. Ebtehal
30 25 5 - Dr. Maha
25 Practical
100
Textbooks :
R. Fessenden and J. Fessenden, Organic Chemistry, PWS Publishers, Latest edition .
Optional reading: Joule and Smith, Heterocyclic Chemistry, Van Nostrand Reinhold, Latest edition.
Topics to be covered:
Part I: Stereochemistry Amino acids
Part II: Classes and Mechanism of reactions
Part III: Heterocyclic chemistry
Aim of the Course
The Course is Designed to Provide the Students with:• Recognize the various classes and subclasses of organic
compounds and how the chemical and physical properties influence their behavior.
• Understand the chemical reactions unique to each class or subclass of organic molecules and their role in synthetic chemistry.
• Recognize the different reaction mechanisms and their importance in synthesis.
• Understand the stereochemistry of organic molecules and the stereochemical courses of organic reactions.
• Understand the role of physicochemical properties, mechanisms, and stereochemistry of organic molecules in biology and pharmacy.
Stereochemistry
Lecture Contents:
•Introduction to stereochemistry.
•Types of isomers.
•Constitutional isomers.
•Stereoisomerism.
•Geometrical isomer.
Stereochemistry
Is the study of molecules on space. i.e. how atoms or groups in a molecule arranged in space relative to each other
It is that part of the science which deals with structure in three dimensions
Is the field of chemistry that concerned with isomerism ( stereoisomerism )
Isomerism
A phenomenon resulting from molecules having the same molecular formula but different arrangement In space
When two or more organic compounds have the same molecular formula but differ in their physical or chemical properties they are called Isomers and the phenomenon called isomerism.
Isomers
Constitutional isomers
Stereoisomers
Optical isomers
Geometrical isomers
Conformational isomers
Constitutionalisomers
Have the same molecular formula but different
connectivity
eg. Ethanol & DimethyletherSame molecular formula, C2H6OBut the atoms in each compound are connected differently
C
H
C
H
H
H
H
OH
CH3CH2OH
C O C
H
H
H
H
H
H
CH3OCH3
Constitutional Isomers
They differ in the way their atom are connected.
1. Chain isomerism2. Positional isomerism3. Functional isomerism
Chain Isomerism
Chain isomers have the same molecular formula but differ in order in which the carbon atoms are bonded.
Predict:
Answer:
Positional Isomerism
Position isomers have the same molecular formula but differ in the position of functional group on the carbon chain.
Examples are:-
Predict
Functional Isomerism
Functional isomers have the same molecular formula but different functional groups. Examples are;
Stereoisomerism
Restricted rotation' of carbon-carbon double bonds
Diastereoisomers are designed cis or trans according to the priority orders or sequence rules [ atomic number ]
Geometrical Isomers(cis & trans)
cis-trans isomers result from restricted rotation
Restricted rotation- caused by either double bond or by cyclic system
The (E, Z) system for Nomenclature of alkene
Alkenes with four different substituent
Which isomer is cis and which is trans?
E-Z systems
-Mostly used in trisubstitutedand, tetrasubstituted double
bonds.
-To name an alkene by E-Z system, separate the double
bond into its 2 end.
-Assign priorities to groups on each C atom.
-Consider each end of the C double bond.
-Assign first and second priorities to substituent group
Priority Rules:
Problem 1: