chapter 1 introduction to organic chemistry
TRANSCRIPT
FHSC1124Organic Chemistry
Introduction to Organic Chemistry
Chapter 1
Chapter Scopes
• Introduction• Homologous series
• Functional groups• Naming/Nomenclature• Isomerisms
Objectives
After this chapter, you will:
• Learn and differentiate functional groups
• Learn to name organic compounds according to IUPAC nomenclature and draw correct structure
• Learn about types of isomerism
Introduction to Organic Chemistry
Introduction to Organic Chemistry
• Organic compounds are classified into different types, such as alkanes, alkenes, alcohols, amines and etc.
• Each type of organic compound contains the same reactive group of atoms, which is called functional group.
E.g. alcohols contain the –OH functional group
Functional GroupsFunctional Group Structure
Alkane
Alkene (Olefin) C=C (ethylenic bond)
Alkyne CC (acetylenic bond)
Alcohol (hydroxyl)
Arenes (aromatic hydrocarbon)
Ar (Aryl)
Aldehyde
R – H
O
R – C – H
R – O – H
Functional Group Structure
Ketone
Carboxylic Acid (carboxyl)
Ester
O
R – C – R’
O
R – C – OH
O
R – C – O – R’
Functional Group Structure
Anhydride
Amide
Amine
Nitrile
O O
R – C – O – C – R’
O
R – C – NH2
R – NH2
IUPAC Nomenclature
• IUPAC International Union of Pure & Applied Chemistry
• The IUPAC nomenclature system is a set of logical rules devised and used by organic chemists to name the organic compounds.
IUPAC Rules
1. Select the longest continuous C chain as parent chain (use root word for the no. of C)
2. Name each of the branch/substituents as an alkyl / aryl group
3. Number the C chain begin from the end nearest to the branch
branch/substituents appear at the lowest no. possible
4. Name each substituent according to its chemical identity & the no. of the C atom to which it is attached
For identical substituent, use the prefix di, tri… & write appropriate C no. for each substituent
5. Separate no. from no. by commas (,) & no. from letters by hyphens (-)
6. List the substituents alphabetically by name di, tri…. don’t count
Functional Group Nomenclature
Alkane End with -ane
Alkene End with –ene
Arene End with –benzene
Alcohol End with –ol
Aldehyde End with –al
Ketone End with –one
IUPAC Nomenclature
Functional Group Nomenclature
Carboxylic acid End with –oic acid
Ester End with –oat
Anhydride End with –oic anhydride
Amine End with –amine
Amide End with –amide
Nitrile End with –nitrile
Prefix No. of Carbons (n)
Prefix No. of Carbons (n)
Meth 1 Hex 6
Eth 2 Hept 7
Prop 3 Oct 8
But 4 Non 9
Pent 5 Dec 10
Base Names
Straight-Chain Alkyl Groups, R
Alkyl group Name (abbreviation)
CH3 Methyl (Me)
CH2CH3 Ethyl (Et)
CH2CH2CH3 Propyl (Pr)
CH2CH2CH2CH3 Butyl (Bu)
CH2CH2CH2CH2CH3 Pentyl• Alkyl groups are named by replacing the
–ane ending of the parent alkane with an –yl ending
Naming of Identical Branch Substituents
No. of substituents Prefix
2 Di
3 Tri
4 Tetra
Isomerism
Definition of isomerism:
• A phenomena where 2 or more compounds have the same molecular formulae but with different arrangements of their constituent atoms
• Such molecules are known as isomers
IsomerismIsomerism
Structural Isomerism
Stereoisomerism
Chain Isomerism
Position Isomerism
Functional Group Isomerism
Optical Isomerism
Geometric Isomerism
Structural Isomerism• Isomers have the same molecular formulae
but different structural formulae
1. Chain Isomerism• The isomers are from the same homologous
series & have the same functional groups but different type of carbon chain.
• Example: C4H10
2. Position Isomerism• The isomers are from the same
homologous series & have the same functional groups but the position / location of the functional group is different
• Same C skeleton
• Example: C3H8O
3. Functional Group Isomerism• The isomers are from different homologous
series & have different functional groups• The chemical & physical properties are
different
• Example: C3H6O
Geometric Isomerism (Cis-trans Isomerism)
• The atoms making up the isomers are joined up in the same order, but manage to have a different spatial arrangement.
• Due to restricted rotation of groups in double bonds & in cyclic compounds.
Example: Geometric Isomerism
C C
Cl
Cl
H
H
trans-1,2-dichloroethene
C C
Cl
H
Cl
H
cis-1,2-dichloroethene
• trans isomer 2 chlorine atoms are locked on opposite sides of the double bond (trans : Latin meaning "across“)
• cis isomer 2 chlorine atoms are locked on the same side of the double bond
(cis : Latin meaning "on this side")
The Effect of Geometric Isomerism on Physical Properties
1. cis isomer has higher boiling point.• Bp depends on the polarity of the molecules• cis isomers are > polar, stronger attractive
intermolecular forces exist between cis isomer
2. trans isomer has higher melting point.• Mp depends on the arrangement & packing
of molecules in the crystal lattice• trans isomer with > symmetrical structure,
can be > closely packed in the crystal lattice
?? Cis-isomer has higher bp
• e.g. 1,2-dichloroethene• 1 side will be more positive charge & the
other side more negative polar• Van der Waals + dipole-dipole interaction • Need extra energy bp increases
?? Trans-isomer has lower bp
• the slight charge on the top of the molecule is exactly balanced by an equivalent charge on the bottom
• No dipole-dipole force as it is non-polar molecule.
• Thus, only held by weak Van der Waals • Less energy needed lower bp
?? Trans-isomer has lower bp
• Trans-isomer• No dipole-dipole force as it is non-polar
molecule.• Thus, only held by weak Van der Waals • Less energy needed lower bp
?? Trans-isomer has higher mp
• trans isomer has the higher melting pointMelting point = solid solution
• In order for the intermolecular forces to work well, the molecules must be able to pack together efficiently in the solid.
• Trans isomers pack better than cis isomers. The "U" shape of the cis isomer doesn't pack as well as the straighter shape of the trans isomer.
?? Cis-isomer has lower mp
• The poorer packing in the cis isomers means that the intermolecular forces aren't as effective be
• Less energy is needed mp lower
Optical Isomerism• Optical isomers are 2 compounds with the
same structural formulae, but one isomer is the mirror image of the other & cannot be superimposed on one another in any orientation
• It occurs when 4 different groups of atoms are joined to a C atom by 4 single covalent bonds.
Optical Isomerism• Occurs because of the tetrahedral bonding
around a C atom• Structures that can exist as 2 optical
isomers are said to be optically active & possess a chiral centre
• Simple substances which show optical isomerism exist as two isomers known as enantiomers
• Chiral centre = atom bond with the 4 different groups, which is normally marked with an asterisk ()
Example: Optical Isomerism
Chiral centre
Example: Optical Isomerism
• It is important this time to draw the COOH group backwards in the mirror image.
Incorrect
Exercise For each of the following molecules, draw the possible stereoisomers and state the type of stereoisomers shown.
(a) C6H5CH=CHCOOH
(b) C6H5CH(Cl)CH=CH2
(c) CH3CH=CHCH3
(d) CH3CH2CH(NH2)COOH
Summary
use IUPAC nomenclature to name and draw correct structure of simple organic compounds with different functional groups.
Differentiate types of isomerism and draw isomers.