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CHM1022 – Week 2 Tutorial

TUTOR: FERA LUCIAWATI


(FERA.LUCIAWATI@MONASH.EDU )
Functional Groups
Alkanes R CH2 CH3 e.g. butane CH3CH2CH2CH3

H H
Alkenes C C e.g. 2-butene CH3CH=CHCH3

Alkynes C C e.g. 2-butyne CH3C CCH3

Alcohols R OH e.g. 1-butanol CH3CH2CH2CH2OH

Ethers R – O – R’ e.g. diethyl ether CH3-CH2OCH2CH3

Alkyl Halides R X e.g. 1-chlorobutane CH3CH2CH2CH2Cl

Amines R NH2 e.g. 1-butylamine CH3CH2CH2CH2NH2


Functional Groups
O
Aldehydes e.g. butanal CH3CH2CH2CHO
R C H

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.

Conformations result from carbon-carbon bond rotation:


Staggered

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”

They have different physical and chemical properties

CH3 CH2 OH CH3 OCH 3


Ethanol Dimethyl ether
bp 78°C bp -24°C

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.

Example: Lactic acid = 2-Hydroxypropanoic acid


Mirror plane
Stereogenic
OH HO H HO H H OH
centre
C
H3C COOH H3C COOH H3C COOH HOOC CH3

Mirror image

These dra 3D-representation


wings do not provide any Bond in the plane
information about stereochemistry Bond projecting away
Bond projecting towards viewer

8 8
Stereoisomers

When a molecule has 2 or more chiral centres, enantiomers and


diastereoisomers are found.

Stereoisomers that are mirror images of each other are called


enantiomers.

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.

See examples on the board!


E & Z Nomenclature
Cahn, Ingold, Prelog system
Priority rules:

Priority is based on atomic number.


The higher the atomic number, the higher the priority (i.e. 1 is higher than 2, 3 and 4).
The atoms directly attached to the stereocentre are examined first.

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

See examples on the board!


Blackman 16.5
Addition Reactions
An Addition Reaction
“Is one where an atom or group of atoms is
added (formally or informally) to a molecule
without the loss of any other atom or group of
atoms”

Occurs typically
in multiple bonds

Revision and Introduction


13
to Organic Chemistry
Blackman 16.5

Addition of HX
Additions are carried out with pure reagents or in a polar solvent such as acetic acid

Additions are regioselective, ie one direction of bond-forming or bond-breaking occurs


in preference to all other directions. Blackman p 726
Markovnikov’s rule: In additions of HX to alkenes, H adds to the carbon with the
greater number of hydrogens
Blackman 16.5

Addition of H2O
Addition of H2O is called hydration

Acid-catalyzed hydration of an alkene is regioselective - hydrogen


adds preferentially to the carbon with the greater number of
hydrogens
Blackman Ch. 2

Mechanism
How do we describe reactions?

But what’s actually happening?

The reaction mechanism describes the formation and


breakage of bonds.

Blackman Ch. 2, p 49-50

16
Mechanism
A single covalent bond
A B

is formed by the
overlap of two single
valence
electron orbitals
bond theory

Revision and Introduction


17
to Organic Chemistry
Blackman Ch. 2, p 49-50
Mechanism
BREAKING BONDS (Lytic)
Heterolytic bond cleavage
Charged products with
paired electrons

MAKING BONDS (Genic)

Heterogenic bond formation


2 electrons from one
starting material

“Normal” arrow
Represents Movement of 2 electrons

18
Curved Arrow Notation
Electrons go from an electron-rich atom
to an electron-poor atom.

All acceptable electron redistributions (bond break/make) must:


1. have the same number of valence electrons
2. obey the rules of covalent bonding
3. differ only in distribution of valence electrons
4. have the same number of paired and unpaired electrons
5. Have a charge balance following the redistribution

Make sure you understand electronegativity!

19
Mechanism of Something Familiar
-

+

MeOH is ê-rich

Carbonyl carbons are ê-


poor - especially with
neighbouring halides!

Break a bond Make a bond


Mechanism of Something Familiar
Describing Functional Groups
Nucleophiles: are electron rich species that donate an electron pair to an
electrophile. They can be neutral or negatively charged.

Electrophiles: are electron poor species that accept an electron pair from a
nucleophile. They can be neutral or positively charged.

Pauling electronegativity of some elements

X = halogen, OH, NR2

22
Addition of H2O
Blackman 16.5

Mechanism.
Step 1: proton transfer to the alkene gives a carbocation

Step 2: a Lewis acid/base reaction gives an oxonium ion

Step 3: proton transfer to solvent gives the alcohol

Blackman p 728-729

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