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H H
Alkenes C C e.g. 2-butene CH3CH=CHCH3
O
O C
Ketones e.g. butanone H3C CH2CH3
R C R
O
Carboxylic Acids CH3CH2CH2COOH
R C OH e.g. butanoic acid
O
Esters CH3CH2CH2COOCH2CH2CH2CH3
R C OR' e.g. butyl butanoate
Amides O
CH3CH2CH2CONHCH2CH3
R C NR' e.g. ethyl butanamide
H
Conformations of Alkanes
Important – “Free rotation” is possible around single bonds
in organic molecules.
Eclipsed
Lower Energy
If a molecule could be
“frozen” to stop the
rotation, a lower
Higher Energy energy state would be
.
Blackman p 700-701 preferred
Chair conformation of Cyclohexane
“drawing tutorial is on Moodle”
When the chair is flipped, all groups in “equatorial” becomes “axial” vice versa.
Blackman 17.1 Isomers
Isomers
Different compounds
with the same
molecular formula
Constitutional Stereoisomers
Isomers with a different Isomers with the same order of
order of attachment of attachment of atoms, but a different
atoms in their molecules orientation of atoms or
groups of atoms in space
Enantiomers Diastereoisomers
Stereoisomers that are non- Stereoisomers that
superimposable mirror images of are not mirror images of
each other each other
6 6
Blackman p 61-63 & p 709-710
Constitutional Isomers
“Two compounds with the same molecular
formula but a different connectivity of atoms”
7
Blackman 17.2 Chirality
Many chiral molecules contain an asymmetric carbon
centre, a so called stereogenic centre.
This is easily identified as a carbon atom attached to four
different groups.
Mirror image
8 8
Stereoisomers
Stereoisomers that are NOT mirror images of each other are called
diastereoisomers.
For any given chiral compound, it will have ONE enantiomer and several
diastereoisomers, depending on the number of chiral centre(s).
Blackman 17.4 Enantiomers & Diastereoisomers
Consider a compound with two stereocentres
It has two stereocentres; 22 = 4 stereoisomers exist
R R S S
R S S R
10 10
Naming Alkenes
Step 1. Identify the longest linear chain with the alkene in it.
Step 2. Count from either end of the chain such that the first carbon of the alkene receives the lowest
number (e.g. 2 NOT 3 for our example).
Step 3. Name any side groups based on “Naming #1”, and assemble the name in the following order.
a) Stereochemical designator (E (entgegen) or Z (zusammen), in italics);
b) Branching point (i.e. 4);
c)-side group name and
d) name of longest linear chain with number for first carbon of alkene embedded.
If priority can not be assigned at this level, the next set of atoms are examined. This process is
continued until a 1 4 designation can be made on the four substituents.
In the case of double bonds (e.g. C=O, C=C), the atoms in the bond are treated as two atoms attached
by single bonds
Occurs typically
in multiple bonds
Addition of HX
Additions are carried out with pure reagents or in a polar solvent such as acetic acid
Addition of H2O
Addition of H2O is called hydration
Mechanism
How do we describe reactions?
16
Mechanism
A single covalent bond
A B
is formed by the
overlap of two single
valence
electron orbitals
bond theory
“Normal” arrow
Represents Movement of 2 electrons
18
Curved Arrow Notation
Electrons go from an electron-rich atom
to an electron-poor atom.
19
Mechanism of Something Familiar
-
+
MeOH is ê-rich
Electrophiles: are electron poor species that accept an electron pair from a
nucleophile. They can be neutral or positively charged.
22
Addition of H2O
Blackman 16.5
Mechanism.
Step 1: proton transfer to the alkene gives a carbocation
Blackman p 728-729